In the peaceful coastal New England town of Capeside, Massachusetts, Dawson Leery, a 15-year-old film buff, lives a fantasy life of movies and filmmaking with his lifelong friends, tomboy Josephine "Joey" Potter and the outgoing and clownish Pacey Witter. On the day before starting the new school year as a sophomore, Dawson meets and falls for newcomer Jennifer "Jen" Lindley who arrives from New York City into the house next door to Dawson's to help her grandmother care for her invalid grandfather. Dawson's new bonding with Jen makes Joey slightly jealous which comes out during a movie outing with her, Dawson, Pacey and Jen. Meanwhile, Pacey finds himself growing in love with a new mystery woman that comes to town, Tamara Jacobs, who turns out to be the new English teacher at Capeside High School. Also, Dawson tries to get into Capeside High's film class, but is denied for being a sophomore.
The class movie hits some trouble, giving Dawson an advantage. Joey falls in love with a visitor to the town. Pacey's school achievements and his relationship with Tamara intensify. Dawson brings his feelings about Jen out into the open.
Dawson turns to Jen for comfort after learning about his mom's affair with her co-anchor, Bob, as well as Joey's knowledge of it. But he regrets doing so when Jen tells him some of her own problems involving her promiscuity and the real reason her parents forced her to move to Capeside. Meanwhile, Pacey and Tamara continue to temp fate with their affair, which was compromised because Dawson accidentally videotaped it.
When a major hurricane strikes Capeside, all the principal characters take refuge in the Leery home, including Joey's very pregnant older sister Bessie and her boyfriend, where Jen's overly religious grandmother does not hide her bigotry towards them. Also, Dawson rages at Jen about her past and at Joey for not confiding in him about her mother's philandering. But when Mitch learns about Gail's affair, he angrily storms out of the house, leaving a tormented Dawson to deal with the fallout. Meanwhile, Pacey takes shelter at Tamara's beach house with his brother Doug, a local policeman, where he ruins his brother's chances to hook up with Tamara by secretly telling her that Doug is gay.
Capside is abuzz with rumors of a teacher's indiscretion, rumors that could prove fateful for Pacey and Tamara. Pacey then takes it upon himself to go before a school board hearing to admit to personally fabricating the rumors to clear Tamara. Meanwhile, Joey and Jen get a life lesson when Bessie is aided by an unlikely source, Grams Ryan, when she goes into labor and gives birth to her baby in Dawson's living room, with Dawson videotaping the whole thing.
After Dawson, Joey, Jen and Pacey individually commit various violations at school, they all get stuck together for an eight-hour Saturday of detention, along with Abby Morgan, a trouble-making imp, where tensions still run high between all of them when Dawson and Pacey turn against each other, and Joey offers a tearful, partial explanation for her personal anger towards Jen.
Dawson feels the heat when Jen is visited by an old boyfriend, named Billy, from New York and whom is unwilling to let go of the past, or her. Meanwhile, Joey lets off a bit too much steam at a beach party by getting drunk after seeing Dawson and Jen together and has to be rescued by Pacey. Also, tensions between Mitch and Gayle reach the boiling point as they attempt to rebuild their marriage.
Hoping to get over his breakup with Jen, Dawson and Pacey join Billy in a boys night out to Providence. Meanwhile, Jen handles damage control after Joey becomes the subject of a rumor at school when a jock tells everyone that he and Joey are physically involved.
A double date finds Jen and Cliff joined by Dawson and a savvy sidekick, named Mary Beth, at Capeside's annual carnival which is revealed to be a plot to make Jen jealous while Mary Beth asks Dawson to help her out by trying to make Cliff jealous as well. Meanwhile, Pacey and Joey grow more close to each other when they work on a school biology project which a comedy of errors leave them stranded on a marsh bog. When Dawson later finds out of their misadventure, it's his turn to become jealous. Also, Mitch and Gail's marriage continues to become strained over him becoming more distrustful of her.
In honor of Friday the 13th, both the film and the date, Dawson plays practical jokes against everyone while he plans a séance for the gang to look up ghosts, until they are all spooked by reports of a serial killer heading towards Capeside. Meanwhile, Jen is asked out by a friendly jock, named Cliff, in which the date ends up at Dawson's house while Dawson, Joey, Pacey bring along a slightly-crazed young woman, named Ursula, who is running away from her psychotic boyfriend.
Jen convinces Joey to enter a beauty competition to win money for college, while Pacey decides to enter to win money for his own apartment. While Dawson covers the competition, with his mother's assistance, Jen begins to regret her breakup with Dawson.
At her sister Bessie's persuasion, Joey goes to visit her father in prison. Dawson tags along and leading them to spend the night in a motel where he finally reveals his true romantic feelings for her, while Joey debates going to France for a semester abroad to escape from her troubled home life in Capeside. Meanwhile, Grams tries to persuade the atheist Jen to act through prayer as her comatose grandfather is admitted to the hospital. Also, the sarcastic Pacey continues quarreling with Doug over Pacey's failing grades, which all emits from Pacey's extremely low self-esteem.
The day after their first true romantic kiss, Dawson and Joey both begin to have doubts about the future of their relationship as Joey forgoes her plans of going to France to be near Dawson. Meanwhile, Pacey decides on a new hairstyle look for himself and becomes chummy to the new girl in town: the neurotic, stuttering Andie McPhee, after they accidentally collide with each other in their cars. Pacey then asks Andie to help him get the attractive head cheerleader, named Christy Livingstone, to notice him. Following the death of her grandfather, Jen debates her own future after figuring out that Dawson and Joey are now a couple. Also, Mitch doubts the future of his marriage with Gayle when he goes to see a divorce lawyer.
Dawson gets in trouble with Joey when he reads an entry in her diary about her true feelings about his fantasy life of filmmaking. Meanwhile, Dawson is so self-involved with repairing his love live that he forgets Pacey's 16th birthday. As a result, Pacey, who also failed his drivers' ed test, decides to throw himself a pier party bash with a little help from Andie. Jack McPhee, Andie's older brother, gets a job at the Ice House restaurant which Bessie runs. Meanwhile, Abby Morgan begins to become a negative influence over the lonely Jen by taking her out carousing for guys and drinking. Also, Gayle confides in Grams, and Mitch with a friend, about their troubled marriage.
An economics class project pairs Dawson and Jen as husband and wife, as well as Pacey and Andie as a married couple. Jen, with a little of Abby's help, tries to take advantage of this project to get closer to Dawson, while Pacey gets to know a little more about Andie's background from Jack. While doing this project, Joey learns that as a single parent, she has a better chance of success in life, but does not see the same for Bessie who begins pressuring her to work harder at the Ice House. Also, Mitch and Gale's marriage continues to deteriorate to a point where neither one wants to be around the other.
Tamara Jacobs, the former Capeside High English teacher who left town to avoid a scandal after her affair with Pacey was almost exposed, shares an awkward reunion with him as she's temporarily back as a real estate agent, who is trying to sell Mitch a warehouse which he hopes to open his own restaurant. The encounters triggers old emotions in Pacey and curiosity in Andie who asks Dawson for advice on Pacey's likes and dislikes. Meanwhile, Joey finds a new joy in art and takes the time visiting a gallery with Jack who shares her newfound love, but Dawson does not have the same interests. Also, Abby tries to get Jen to help her flirt with an attractive seaman, named Vincent, who rejects Abby's over-played advances, but accepts Jen's more softer approach.
Emotions run high during the monthly night of the full moon when parental problems cast a pall over Dawson and Joey's new romance as Dawson finds himself stuck in the middle of Gail and Mitch's hostile feud over people they invite over; he with Miss Jacobs over the property and she with a new co-worker. Meanwhile, Pacey is troubled when he tries to meet Andie's elusive parents, and sees first-hand the home life that Andie avoids which involves her delusional mother unable to let go of Andie and Jack's older brother whom died the previous year. The rife between Jen and Abby increases as Jen invites Vincent over to her house for a date. Left alone to run the Ice House, Joey and Jack share a 'tender moment' during a power outage.
Dawson is rocked by two setbacks in his life. First he learns that Mitch and Gail have decided to separate. Then later at Capside's formal Homecoming dance, he learns about the kiss between Joey and Jack, setting off a chain of fireworks and events that shatter his lifelong friendship and newfound romance with Joey. At the same time, the night gives Jen a chance to use Joey's mistakes to try to get back together with Dawson, but it doesn't work. Also, Pacey tries to be honest with Andie, but ends up breaking her heart when he flirts with cheerleader Christy Livingstone.
Faced with a difficult English test, Dawson, Joey, Pacey, Jen, and Andi have an all-night studying session at Chris Wolfe's house. During this time, a purity quiz reveals the innermost secrets of all involved, including Pacey's fling with the departed Miss Jacobs, as well as Chris' motives to sleep with Jen, who reverts back to her promiscuous personality. The grouping also reveals the rage and jealousy in Dawson over his and Joey's failed relationship, in which he confides in Chris' younger sister, Dina, about his life problems.
After Dawson gets a $2,500 grant from the Boston Filmmaking Association following his win with his horror film, he asks Joey to help him work on his next film. But she refuses for she wants to have a life of her own. That evening, Joey's 'semi-date' with Jack for a moonlight picnic prompts a resentful Dawson to join Jen at a bash house party, thrown by Chris Wolfe, where she gets drunk once again and he ends up saving her from doing some things she'll regret. Meanwhile, Pacey proves his worth when Andie's mother has another psychotic breakdown during a study session at her house. Also, Mitch cannot understand Dawson's views on their divorce.
Andie decides to run for student body president and asks a reluctant Joey as her running mate. But Andie's run lands her on a campaign trail of tears when the devious Abby learns and begins advertising her dysfunctional family situation. Meanwhile, Jen helps Dawson take steps to deal with his powerlessness over his parent's divorce by taking him out on a delinquent spree of pranks as well as a moonlight swim in the nude. Also, Jack shuts out Joey for he does not want to talk about his family problems with her or anyone.
A series of 'horrifically epic' tryouts for his latest movie project, now involving a teen romance, prompt a steamy dialog between the two stars Chris and Abby, while director Dawson and producer Jen decide that they may have to recast Abby's role. Meanwhile, Jack poses in the nude for Joey for her art class' project sketch, who feels herself drawn towards intimacy. Also, Pacey sets out to fulfill Andie's dream date on his own with a romantic dinner, and a encounter in a hotel room.
Abby and Chris find an anonymous love note at school and set out to find who wrote it. Abby figures out that the author and intended recipient apparently had sex the night before and, in her true devious fashion, she sets out to expose the affair. The three suspect couples are: Dawson and Jen; Joey and Jack; Andie and Pacey. Abby and Chris work from clues about Joey's night of sketching after discovering her drawings of a nude Jack, while angry Dawson sets out to find Joey and Jack, while Pacey becomes distant towards Andie after their romantic dinner. In a true Gothic themed mystery novel backdrop complete with a thunderstorm and lighting, Abby and Chris gather all six suspects into a classroom after hours to bring out the author and which couple, if any, went "all the way".
The gang explore uncharted waters when the girls, Jen, Joey, Andie and Abby spend a day with Gail doing a TV report on teenage behavior amid the tensions between all of them over Jen and Joey's continuing feud and Abby's continuing insensitivity. Meanwhile, Dawson and Pacey explore their own uncharted waters when they go on a father-son fishing trip with Mitch and Pacey's grumpy and critical father, Sheriff John Witter, as well as Jack whom Pacey invites to tag along which brings out more tension between Dawson and Jack.
The filming of Dawson's new movie brings back memories for both the filmmaker and for Joey, who grows to dislike Devon, the actress playing her, as well as Chris, who's playing Dawson's character. Meanwhile, Jen, now working as Dawson's producer, meets a new potential boyfriend for herself, Tyson 'Ty' Hicks who is hired as a props man on Dawson's set, along with other Capeside High volunteers. Also, Pacey learns that Andi is bi-polar after he finds anti-depressant pills in her trash, which prompts her to believe that Pacey is more of an interference than a help in her life.
Capside High is abuzz with the gossip mill after Jack bears his soul in a English assignment and is forced to explore his innermost secrets while reading a poem he wrote aloud in class, leaving Dawson, Joey and Andie shaken by the implications of what it all means: Jack happens to be gay. Meanwhile, Pacey tries to defend Jack in the face of his adversarial English teacher, Mr. Peterson, and ends up getting in trouble when he assaults the petulant Mr. Peterson which causes a riff between Pacey and Andie. Also, Jen finds Ty Hicks to be full of surprises of not only being part of a bible study group, but having a liking for blues music by taking her out to a local jazz club.
On Dawson's advice, Joey attempts to heal the wounds of her romance with Jack which has been left shattered by rumors and innuendo. Meanwhile, Jack and Andie's father, Joseph McPhee, arrives in town for a get-together which brings out old family tensions which leads Jack confronting his innermost secrets. For the first time in his life, Pacey stands up for what he believes in when he takes on the mean-spirited Mr. Peterson. But the consequences of his convictions are more than Pacey could have imagined when he's suspended from school and Peterson makes his personal agenda to fail Pacey with unethical means. Pacey then sets out to ruin Mr. Peterson by investigating and challenging his authority with a code of conduct book over his teaching methods. Also, Jen thinks that Ty may not be the guy for her when she sees little amusement in his stereotypical comments especially over Jack's true sexual orientation, while Grams is surprisingly understanding and supportive.
On Dawson's 16th birthday, he, Pacey and Andie follow her therapist's advice and throw themselves into an unabashed night of recklessness where both Dawson and Andie get drunk at the jazz club and end up on stage singing the blues. Meanwhile at the Leery house, Joey is organizing a surprise party for Dawson. But the longer the guest of honor is a no-show, the more she is subject to surprises of her own. Abby and two of her girlfriends crash the party and taunt Jack over his recent 'coming-out.' Jen and Ty finally face up to their potentially irreconcilable differences in which they break up for good. Also, Gayle and Mitch come to decisions about how to raise their son in light of their divorce.
Dawson's confidence as a filmmaker is shaken when his new film class teacher, Nicole Kennedy, a Hollywood movie studio executive on sabbatical in Capside, speaks her mind and tells him the painful truth about his new romance movie and its faults. Meanwhile, the future is unsure for Joey when she visits a Gypsy fortuneteller at the annual Capeside Carnival, who advises her to be open to every new opportunity that crosses her path. Shortly after, Joey stumbles into Colin Manchester, a gorgeous photographer who brings out Joey's free-spirited side during a wild photo shoot. Also, Jen tries to persuade Grams to go out with an old flame, and Pacey becomes more uncertain about where he stands with Andie.
With Joey's father back in town after being paroled from prison, he persuades Bessie to expand the Ice House to cater weddings. Needing help, they enlist the services of the gang as staff. Andie tells Pacey that she hates weddings, but he loves them, while Joey doesn't think her ex-con father should be seen around Capside. In a comedy of errors, Jack and Dawson battle to help a scared bride, Andie and Pacey scramble to fix the wedding cake, while Mitch shows up with his new girlfriend Nicole Kennedy making Gayle sad, and Dawson angry. Also, the trouble-making Jen and Abby crash the ceremony to steal some food and liquor for another night out which eventually leads to tragedy when Abby falls off a pier while drunk... and drowns.
In the aftermath of Abby's death, all of Capeside is attempting to 'whitewash' her life. But all the hypocrisy is making Jen angry knowing that Abby's 'good life' was all a scam. At Abby's funeral, Jen delivers part of the eulogy where she embarrasses Grams by announcing that Abby taught her the falseness of God. Meanwhile, Abby's clueless mother asks Andie to deliver the eulogy after mistakenly thinking that they were friends. Joey is afraid to attend the funeral which brings back bad memories of her own mother's funeral while Dawson persuades her to overcome her fears. Also, Gail tells Dawson that she has accepted a job offer as an TV executive in Philadelphia.
With Dawson and Joey back together, he decides to take her out to a romantic dinner for old time's sake. But also eating out are Mitch and Nicole. On top of that, the restaurant, not realizing that there are two Leery parties, has only has one table available, forcing all four of them to sit together which immediately lights up tension. Also at the restaurant are Jen and Gail where Dawson, Joey and Jen attempt to reunite Gail and Mitch after Nicole walks out from the constant arguing. But the ploy only works temporarily. Meanwhile, Andie begins to fall into insanity when she begins changing her hair color from blond to brown, and begins having ghostly encounters with her deceased brother, Tim, while Pacey and Jack catch on and try to confront her with her mental state.
Concerned for Andie's well being, Jack phones their father who arrives back in Capeside where he announces that he intends to take both Andie and Mrs. McPhee to Providence for treatment in a mental hospital. Both Jack and Pacey are stunned at the news which leads to Pacey and Andie to decide whether her mental wellness is more important than being together. Jack also must decide if he wants to go with Andie and their mother, or stay alone in Capeside. Meanwhile, Dawson is preparing his film class' final exam by videotaping all individuals involved as well as helping Joey's father, Mike Potter, extend the Ice House for Bessie. After being shunned by everyone, Jen wonders where she'll live after her parents tell her by phone that she is not welcome to come back to New York.
Dawson's suspicions about Mike Potter become confirmed when he sees him selling drugs again and is torn on whether or not to tell Joey or leave things as they are. But Pacey's grumpy and misanthropic father, Sheriff Witter, is already suspicious and has the Ice House staked out hoping to catch Mike Potter in the act in which the restaurant is set afire by Mr. Potter's competitors. Meanwhile, Gail tells Mitch that she has decided to take the job offer in Philadelphia and wants to leave as soon as possible with Dawson. Pacey becomes more depressed as his school grades start decreasing now that Andie is gone from his life and his domineering father verbally bullies him. Also, Jen becomes more and more depressed over Abby's death in which Jack wonders if she is suicidal. Eventually, Grams asks Jen to come back to live with her and Jack is welcome to live with them too.
After spending the summer with his mother in Philadelphia, Dawson returns to Capeside and meets a beautiful, outgoing, young woman, named Eve Whitman, on the bus from Philadelphia. Eve soon brings trouble to Dawson's ho-hum life when he accidentally wrecks his father's boat during an outing with her and tries to come up with $3,000 to repair it before Mitch finds out. So, Eve helps out by throwing a rave party at the Leery house with strippers from the club she works at. Meanwhile, Joey, who has frozen Dawson out all summer for forcing her to rat out her father, realizes that she still has feelings for him again when they meet during the first day back at Capeside High as juniors. While working at the Capeside Marina, Joey deals with the come-ons from her sexist boss Rob Logan. Jen gets more than she bargained for when she tries out for Capeside High's cheer leading squad and faces off in a war-of-wits against the mean-spirited head cheerleader, and acquires her position. Also, Mitch gets a new job as Capeside High's varsity football coach, and a new charismatic, but very stern, principal, named Howard Green, arrives to administrate the school.
Dawson is recruited by Mitch and Principal Green to produce a film for the football pep rally, while the mysterious Eve continues to temp Dawson. Meanwhile, Pacey enlists Joey's help for help in bringing Andie back to Capeside. But Pacey's and Andie's long-awaited reunion doesn't go exactly as Pacey intended when a guilt-ridden Andie tells him about a fling she had of her own and as a result, Pacey breaks up with her. Also, Jack is asked to join the football team, the Capeside Minutemen, and then comes to an unexpected understanding with his father who has returned to Capeside after moving his struggling business to live near Jack and Andie. Also, head cheerleader Jen has a meeting of minds with the new Capeside quarterback; the rookie freshman Henry Parker.
Dawson is stunned when Eve presents him with stolen copies of the school's PSAT's and everyone is tempted to cheat, including Joey whose scholarship to Harvard is dependent on her SAT scores. But when the test goes missing, Dawson wonders who stole it and accusations run high, especially with Pacey. Meanwhile, Jack feels that the whole football team is verbally and physically beating down on him because he is gay, while Henry Parker asks Jack for advice on talking to Jen. Also, Rob Logan continues to make Joey's life difficult at work after she turns down an offer to go on a date with him.
Mitch and Dawson are at odds with each other again when Dawson moves forward with a news piece for his mother's Philadelphia station using Mitch's star player, Jack, as his subject matter, even though Mitch is vehemently opposed to it. Meanwhile, Joey and Pacey find themselves in cahoots when they must pay the price for ditching school for the day so Pacey can work on a 'dream boat' he plans to sail around the world in, while Andie panics and jumps to conclusions when Principal Green wants to meet with her after school after mistakenly thinking that he knows about her cheating on the PSAT's. Also, Jen goes to great lengths to remove herself as head cheerleader due to the stress of being in that position, but is shocked at the end results which involve the painfully shy Henry Parker.
During a late-summer heat wave, Dawson plays detective when Eve's mysterious ways, including breaking and entering at Grams house, cause him to wonder about her reasons for being in Capeside and he gets Pacey to help him. But Eve is too slick for Dawson's inept detective ways and throws him off balance every time. Meanwhile, Joey's misgivings of Rob lead her to crash his date with Andie at the movies which leads to him firing her. Also, Jack goes against Jen's wishes and sets her up for a rendezvous with Henry.
Nominated for Capeside's Homecoming Queen, Jen wins and is put in charge of planning the Annual Homecoming Queen Gala, where she shocks the prim-and-proper committee president, Constance Freckling, and the entire town with the entertainment, while Jen also asks the painfully sky Henry to be her date. After Joey and Pacey save Andie from the libidos Rob, she wants to get back together with Pacey. But Joey becomes suspicious that Andie may have orchestrated the event to make Pacey her savior. Meanwhile, Dawson is distressed with his mother, Gail, unexpectedly returns from Philadelphia, and soon learns that she was fired from her job, while he is torn about telling Jen the scandalous secret he has about the departed Eve.
Dawson recruits Joey, Pacey and Jen to be his guerrilla crew on a documentary for history class about Witch Island, a local spot shrouded in mystery for its reputation for being haunted by witches. During their work, they are haunted by tall tales of witches and love lost that has Dawson and Joey questioning their failed romance and Jen and Pacey on considering a new kind of friendship. Back at school, Andie takes her new job on Capeside's disciplinary committee a little too seriously when she tries taking back the halls of the outgoing students.
When Jen's estranged mother, Helen, unexpectedly arrives in Capeside on Thanksgiving morning, Dawson confronts her about her secret past involving Eve, and makes a decision to help bridge the gap between Jen and Helen Lindley during the dinner at the Leery house where Grams takes over the cooking munch to Gail's chagrin. Meanwhile, Jen continues to pursue a new type of friendship with Pacey. Mitch and Gail make known to Dawson the future of the Leery family. Joey, Bessie and baby Alexander join the Leerys for Thanksgiving after their turkey dinner literally falls through. Also, Jack and Andie end up attending the Thanksgiving feast at the Leery house after being left alone by their father for the day, and Pacey soon follows suit after apparently being unable to stand Thanksgiving at his house with his crude, crass, and drunkard parents which makes both him and Andie uncomfortable with each others presence.
Dawson becomes suspicious of Pacey's awkward behavior and misconstrues his actions when he learns that Pacey has been spending time with Joey. As it turns out, Joey has asked Pacey to be her ballroom dance partner in exchange for tutoring him in math. Meanwhile, Pacey begins to doubt about moving forward his secret, no-strings-attached, relationship of sex with Jen. Also, Andie urges Jack to meet a gay student from a nearby town who contacted him via the Internet after seeing Dawson's news story.
Dawson, Joey, Jack and Andie spend the weekend at Boston University for an advanced look at college and where Dawson has entered his Witch Island documentary in a student film festival. But he finds the reception not to his liking along with recommendations from Nikki Green, an aspiring student director of her own. Elsewhere on the campus, due to a clerical error, Joey's weekend guide is not what she expected as it turns out to be a guy, named A.J. Moller, who shares her love of the same literature. Meanwhile, Andie's pursuit for an advanced admissions interview leads her to some inspirational advice from an unlikely source: a career secretary. Also, Jack takes a risk and explores the local gay community.
Dawson experiences an identity crisis when Nikki, who happens to be Principal Green's daughter, arrives in Capeside and gives Dawson advice on his future as an aspiring young director like her. Joey experiences her own crisis when Dawson won't open up to her about the pain of his parents divorce. Meanwhile, during a weekend outdoor folk concert, Jack's first efforts to hit on another guy are rebuffed when the man, Ethan, only wants to be friends. Elsewhere in the camp, Jen realizes that she may have passed up the chance at something special with Henry. Also, Pacey and Andie uncomfortably find themselves sharing the same after school activity of planning a school play of 'Barefoot in the Park,' with Pacey in the lead role, and Andie as the assistant director.
Joey's friends and their families work together to make sure that the opening of Potter's Bed & Breakfast is a success and that she and Bessie don't lose everything they have after Pacey surprises them with a visit from a prestigious travel critic. Meanwhile, Jen admits her concerns to Grams about getting close to Henry. Jack considers moving back home to his own house after hearing Andie's loving plea. Also, Dawson tries to understand the connection between his parents after their divorce.
Dawson makes the radical move of dropping out of film class to spend some time re-evaluating his teenage years against Nikki's advice. Meanwhile, Joey is torn between attending Pacey's opening night and her date with A.J., who has come to Capeside for the day. Before opening night of the school play of 'Barefoot in the Park', Andie must take over as director when the faculty director, Mr. Broderick, becomes ill and she tries to persuade Pacey to act out his feelings when he gets stage fright. Also, Jen agrees to go out on a date with Henry by taking him out to see the play. But she throws him another block by bringing Grams with her.
Joey questions Dawson's state of mind when he and Pacey decide to lead her and their friends to a secret location party on a golf course hosted by Matt Caulfield, a wealthy and snobbish student connected to a clique of spoiled rich kids from school, infamous for their complete and utter debauchery. Meanwhile, Jack's ex-girlfriend, Kate Douglas, arrives from Rhode Island for a visit while nursing a broken heart, but is unaware of Jack's coming out. Also, Jen's first date with Henry is a Valentine's Day she won't soon forget when he passes out after donating four pints of blood to pay for their romantic dinner at a fancy restaurant.
Joey is chosen to be part of a group of students to paint a school mural, but when hers is defaced before the unveiling, Dawson offers words of encouragement while Pacey takes action and risks suspension when he goes in search of the culprit whom he suspects to be Matt. When Andie's PSAT scores rank among the best in the country, she feels tremendously guilt-ridden and gambles with everything she has worked for by telling Principal Green about the previously stolen PSAT test. Also, Pacey moves in with his brother, Doug, when their divorced sister and her kids move back into the Witter house and take over Pacey's room.
Joey relies on the support of Pacey and A.J. to rally the students in a major school protest against the school superintendent, Dr. Fielding, after he forces Principal Green to resign for expelling Matt Caulfield who destroyed Joey's mural after the guy's wealthy and powerful parents threaten the school board with a lawsuit. Meanwhile, Dawson and Gail both go back to their respective places in back and in front of the camera to produce a piece about the ongoing school protest which ruffles more than a few feathers of the school board hierarchy as well as Gail's old rival; a reporter named Sherry Eisle who "stole" Gail's old job back in Philadelphia and is now covering the story in her own self-serving and bias way.
Joey travels to Boston to visit A.J. where he is about to receive a critic writing award and meets his childhood friend, Morgan, whom Joey sees as a clone version of herself and her growing feelings for Pacey. Back in Capeside, to avoid suspension, Pacey becomes a mentor to a nine-year-old boy, named Buzz Thompson, and must contend with the kid whom is a little version of himself: a neglected and abused little boy - with a big attitude. Meanwhile, Dawson asks Mitch to help as a chef with the opening of Gail's restaurant which makes Gail angry as she wants nothing to do with her ex-husband.
Pacey hopes that an overnight camping trip by taking Dawson to their favorite childhood camping spot will help ease the pain when he prepares to tells Dawson about his romantic feelings for Joey. But their plans get interrupted when Buzz and two of his friends come along. When Dawson brings up memories about their loyal friendship, Pacey chickens out and decides not to tell Dawson. Meanwhile, Joey deals with the emotional fallout from her kiss with Pacey by spending a girls' night out with Jen and Andie. But to Jen's surprise, they stumble upon a 15th birthday party for Henry at the local roller skating rink that she was not invited to. Also, Jack clashes with his father when Ethan arrives at his house for a visit in which Ethan gets caught in the middle when Mr. McPhee bonds with him and not Jack.
Dawson invites Joey, Andie, and Pacey to spend Spring Break in the mountains of Vermont at his Aunt Gwen's home. But the trip is filled with tension as Joey and Pacey continue to battle about their feelings for each other and Andie becomes intrigued with the gang's childhood friend, Will, who is visiting. Back in Capeside, Jen, working as the hostess at Gail's new restaurant, Leery's Fresh Fish, becomes surprisingly territorial when a waitress, named Shelley, flirts with Henry who's now working there as a busboy. Also, Gail and Mitch question their current situation over being partners in the restaurant.
In this unusual episode that replays the same day's activities from three different perspectives: after Pacey unveils his new sailboat, named 'True Love', he and Joey vacillate on the ways to tell Dawson about their feelings for each other. But each time they decide to tell Dawson about them being romantically involved, they chicken out. But when both Pacey and Joey get together and decide to tell Dawson about them, Dawson's angry reaction is what they hoped they wouldn't get: Dawson reveals that he already knows when Jen had earlier that day told him about Joey and Pacey after assuming that they told Dawson. Meanwhile, Andie, who thought she was over Pacey enough to date, accepts a date with Capeside visitor Will, but their first date is ruined when she also learns about Joey and Pacey now a couple. Pacey also leaves the trouble-making Buzz with his brother Doug for the entire day as Andie deals with her feelings for will, Also Jen deals with Henry who wants to take their relationship to the next level.
As Capeside prepares for the Annual Spring Regatta boat race, Dawson and Pacey compete with each other for the winning trophy, only Joey is tired of feeling like the prize. Meanwhile, after many weeks of mixed messages, Gail makes the first move with Mitch. After Jen finally forgives Henry for his one-track mind, he gives Jen the most romantic night of her life with a moonlight picnic atop a building overlooking the bay.
Dawson, Joey and Andie prepare their own unique prom when they learn that the committee has scrutinized Jack's selected male date Ethan. Dawson, who has invited Joey to be his date, uses the special evening to try to win her back and make Pacey jealous. Andie persuades Pacey to be her escort, but her evening ends by her consoling him about his love life uncertainties. Also at the prom, Jen becomes outraged with Henry when he reveals he is leaving Capeside for the summer to attend football camp in Ohio, and Gail and Mitch celebrate their new found romance.
Pressured by two parties, Joey ultimately must choose between her love for Dawson and her new feelings for Pacey who's planning a summer getaway by sailing down the coast on his new boat, 'True Love.' Meanwhile, Grams talks about love and regret with Jen over the departed Henry, and encourages her, with Jack and Andie tagging along, for an all-night drive to Ohio so that Jen can see Henry one last time. They then take Jack to Boston to see Ethan who tells him that he has returned to his gay boyfriend. Also, Mitch and Gail decide to get remarried and have the ceremony at their house with Dawson as the best man and Joey as the maid of honor. At the end, Dawson encourages Joey to make a move to follow her own path, and she runs off to join Pacey on his boat, leaving Dawson emotionally beaten and alone once again.
Pacey and Joey return from their summer vacation at sea where they have to deal with Dawson's feelings, who has been deeply hurt for the past months while he and Jack made money by painting houses. At first, he doesn't want to talk to either one of them, but at a drive-in theater, Jen convinces him to talk to Joey. Meanwhile, Pacey's other older sister, Gretchen, arrives in Capeside after taking time off from college and moves in with Doug, making Pacey homeless since he does not want to live with Doug or their hostile parents anymore. So, he asks Joey to let him crash at her B&B house for a while. Dawson confides in Jack about Gretchen, for whom he had a secret crush a few years ago. Also, Andie meets two French guys during a beach outing where she becomes attracted to one of them.
Joey is looking for a new job and gets one as a waitress at the Yacht Club Restaurant pretending to know a very affluent family. But she is tricked by her boss' snobbish, trouble-making son, Drue Valentine, who sees through her lies, but decides to let her stay on in order to get to know her better. Meanwhile, Mitch, now working as a guidance counselor at Capeside High, tells Pacey he's not going to graduate unless he makes up for his bad grades. Pacey doesn't want Joey to know, but Mitch tells Dawson, who tells Joey. Gretchen also finds a new place to live in the form of a wretched beach front house, and Pacey willing moves in with her. Jen gets ticked off after the departed Henry breaks off their relationship by e-mail whom he sends to Jack instead of her.
Pacey, enlightened by getting good grades, decides to take a sail on his boat and takes Jen with him for company. Meanwhile, Andie has an interview with Drue's mother for a college acceptance. But her medical records get in her way in which the egotistical and snobbish Mrs. Valentine worries about Andie's mental stability and outright denies her the spot. Everyone's plans change when a big storm rolls into Capeside, trapping Pacey and Jen at sea where Dawson and Joey steal a motorboat, owned by a cranky old resident, A.I. Brooks, to rescue them while Andie takes control of the situation at the Yacht club to wait out the storm. At sea, Jen and Pacey admit to each other their biggest regrets in life. Jen regrets never being in love, despite her feelings for Henry, and Pacey regrets the destruction of his friendship with Dawson.
Everybody starts to think about their future, and how they are getting into college with Joey concerned about Pacey not having grades good enough to graduate and she being Number Four among the top 10 best in school. Drue makes everybody think it's Jen's birthday so he can throw a party and make the moves on her in which it's revealed that that they've known each other when he used to live back in New York. At the gathering, a worried Joey gets drunk and says some concerning things to everyone involved. Meanwhile, Andie takes over Jack's applications for college and drives him crazy with her obsession over it while he is recovering from a pulled shoulder he gets at football practice. Gretchen gets a job as the bartender at Gail's restaurant, and talks with Dawson about his life problems and hers about the real reason why she dropped out of college.
Gail drops a bomb on Mitch and Dawson, saying that she might be pregnant, but she is conflicted whether or not to keep her baby. As a result, Dawson seeks solace with his growing hobby of photography and confiding in Gretchen about his troubles. Meanwhile, Joey seeks advice from Jen because she has the feeling sexual intimacy with Pacey is approaching. Jen tells her to go to the clinic as prevention. Bessie finds out and berates Joey about the risks of sex. Also, Jack and Andie are coaching a little league of soccer kids, and he soon lands in an awkward situation when a teammate's older sister starts to flirt with him. He feels pressured to tell her that he's gay, but he soon regrets it when most of the parents turn out to be homophobic.
Andi gets early acceptance into Harvard, exciting Jack and their father. But accomplishing what should be the biggest thing in her life doesn't make her happy. She decides to explore different paths in her life by going to a rave with Jen and Jack. Andi steals an Ecstasy pill from Jen, which reacts badly with her anti-depressant. Meanwhile, things get awkward during the party when Gretchen brings along Pacey, Joey and Dawson, who is growing more attracted to Gretchen. Also, Mitch and Gail decide to keep their baby.
While Andie is recovering from her near-fatal drug overdose, Jack blames Jen for the incident, while Jen blames the deranged Drue for her life falling apart after he turns everyone, including Grams, against Jen by saying that she deliberately slipped Andie the ecstasy. Andie's father tells her that it would be better if she were to spend the rest of the year in Italy with her aunt, since she already has the credits required for an early graduation. Meanwhile, Joey is conflicted when she must ask Dawson to say a good word for a college acceptance form. Also, Dawson continues painting the misanthropic Mr. Brooks' house and realizes that the old man has his own personal life problems with his estranged family.
A sailboat owned by Capeside High's pompous Principal Dave Peskin, with "Class of 2001" written on the sail, and with his pet dog aboard, is found in the school swimming pool as part of a major school prank. As a result, Mitch Leery and Principal Peskin are after the guys who did it in which Dawson, Pacey, Jack and Drue are main suspects. Since, the dog that was on the boat instantly recognized Jack, Pacey had access to the yacht club and Dawson had access to the school keys. Each one has alibis for that day; Jack was at the soccer field with Jen to help plan a game. Dawson was cleaning Mr. Brooks parlor where he discovers that the that the old man was a former filmmaker from the 1950's. Pacey was with Doug on a routine police patrol where they squabbled about Doug's well being. Drue, despite his denials, is revealed as the culprit. But at the end, Joey finds out that Dawson, Pacey and Jack all teamed up to pull it off and to get Drue into trouble.
Jen reveals an important decision she's made with regards to college while Jack and Grams make a decision on their own for her. When Dawson comes up empty with answers to an important question on his college essay on registration for USC Film School, he turns to Mr. Brooks for inspiration and learns that Mr. Brooks' life in Hollywood eerily parallels Dawson's own life when Mr. Brooks left the filmmaking business after his best friend and girlfriend got together. Meanwhile, Pacey accompanies Joey to a formal party at the Yacht Club for prospective Worthington College students where the visiting dean, Walter Kubelik is impressed... with Pacey. Also, Gretchen takes over planning for Gail and Mitch's Christmas party at the restaurant where Mr. Brooks has a meeting of minds with Grams Ryan.
When Bessie takes a weekend getaway, Joey's hoping to get some studying done. But between her responsibilities at the B&B and Pacey's affections, Joey's hard pressed to find a moment alone to study for an English exam, and as if that wasn't enough, she's trying to cope with her feelings about having seen Dawson kiss Gretchen the other night at the Christmas party. Pacey's got his own issues with that 'kiss' and he's convinced Dawson and Joey need closure, once and for all. Meanwhile, Dawson's collaboration with A.I. Brooks on a documentary on his life story begins, which rejuvenates Dawson's filmmaking spirit and learns more about Mr. Brooks, whom never got over his best friend stealing away his girlfriend. Also, Jen takes Jack to a "Gay-Straight Coalition" meeting in the hopes that he'll meet some gay friends. But Jen seems to fit in with the crowd more than Jack does, who meets the militant founder Tobey.
Pacey learns that Dawson and Gretchen are dating which doesn't suit him at all. So, Pacey tries to get Gretchen and her ex-boyfriend, Nick Taylor, back together when they go on a road trip to pick up her car at her college in Providence. Back in Capeside, Joey has her fair share of problems when she gets locked in a storage closet at the Yacht Club with none other than the loathsome sociopath Drue Valentine, whom has set up the whole thing to avoid visiting his estranged father in New York. Meanwhile, Dawson observes the feelings growing between Mr. Brooks and Grams and fears that Grams will get hurt when she finds out that Brooks, like her last husband, is terminally ill with cancer.
Joey decides to help throw a surprise 18th birthday party for Pacey at his parents house, not knowing about Pacey's 'birthday curse'. The party goes haywire from the start as Joey finally sees why Pacey hates his dysfunctional and annoying family so much; his domineering, drunkard father; his overbearing, delusional mother; and his divorced sister Kerry and her three children, make everyone feel uncomfortable, and Doug later joins in and gets them to embarrass Pacey with stories from his past. Meanwhile, Dawson becomes upset when he feels that Gretchen doesn't want anyone to know about their growing romantic relationship and postpones their first real date to go to the party. Also, Jen is paired with Tobey for a community service project that evening of being the town's designated driver for drunken college kids.
Mrs. Valentine forces Joey to go on a double date with Pacey to accompany Drue and his wealthy, dim-witted, girlfriend, Anna Evans, to make sure that Drue behaves himself. Of course this isn't an easy thing to do when Joey starts to get concerned over the attention that Anna is bestowing on Pacey. Meanwhile, Dawson has his own problems when he and Gretchen go out with two of her college friends and he realizes the span in between their ages. Also, Jack finally gets some positive attention from Tobey when he asks Jack for help in teach reading to grade school kids, and Mr. Brooks becomes more weaker from his illness during the final completion on Dawson's documentary. Knowing that his days are numbered, Mr. Brooks tells Dawson to continue to follow his dream as a filmmaker and not let the love of his life (Joey) slip away, and end up like him: a bitter, misanthropic, lonely old man.
While the rest of the school goes to the snowy mountains of Vermont for a ski weekend, Dawson stays behind to help Grams keep a bedside vigil at the hospital for the near-death Mr. Brooks. But things become complicated when Dawson learns that Mr. Brooks had earlier asked him to sign a medical clause which leads him to be forced to make an impossibly hard decision to decide whether or not to cut off Brooks' life support systems. Meanwhile, the ski trip evening takes an unexpectedly romantic turn when Jen sprains her ankle, she breaks into her room's mini-bar, gets drunk and nearly sleeps with Jack. At the same time, Drue and Anna Evans sneak into the events pretending to be another couple since Drue has been banned from the ski trip and Anna does not go to school at Capeside. Also, Pacey and Joey find their own ways to keep warm on the cold night by taking their relationship to the next level.
Unusual episode about four separate plots told in chronological order rather than concurrently as in previous episodes. "About Last Night": Left behind at the ski lodge, Pacey and Joey are forced to go home by bus where they talk about their sordid night before where he is insecure about his performance and she brings up her own insecurity. "The Big Picture": In Capeside, Dawson is forced to face Mr. Brooks' death by going through his belongings with Gretchen. But soon, Dawson gets surprised to find out that he is Mr. Brooks' will and finds himself with a lot of money in his hands, and no idea of what to do with it. "Excess Baggage": As punishment for breaking into her hotel mini-bar and getting drunk during the class ski trip, Jen is forced to see a psychologist where she can discuss her "inner teen issues." But Jen finds the psychologist, Dr. Tom Frost, to know more about Jen than she does about herself. "Seems Like Old Times": Joey's path with Dawson's collide when they spend an evening catching up on the past weekend and its many happenings. Dawson thinks Joey is different in some way. Here, he asks her the big question: did she or did she not have sex with Pacey during the ski trip? Torn between hurting her best friend by being honest, or lying to him, Joey outright lies and says she didn't sleep with Pacey.
The results of the Senior Polls have ramifications for Dawson, Joey, and Pacey, as the three try to ignore the taunting of the poll master, who happens to be Drue Valentine. While Pacey and Joey try to have some time alone together at his and Gretchen's house, Dawson finds his first night alone with Gretchen more awkward than he'd expected. Gretchen becomes angry and snappish with everything after she learns that Joey lied to Dawson about having sex with Pacey. Meanwhile, Jack becomes resentful when Jen drags him along with her to follow Dr. Frost to find out more about him and they end up going to a poetry reading group to stalk him out.
While Joey glows after being accepted into Worthington University, Dawson is forced to face a crushing rejection when he is denied to NYU. Joey's elated mood, however, is tempered by a sobering realization due to the fact her sister, Bessie, runs a B&B she can't afford the $15,000 tuition requirement, until Dawson proposes a surprising solution: loaning her the money Mr. Brooks left for him in his will, which increases her guilt for lying to him about sleeping with Pacey. Meanwhile, Jen and Jack have nothing but options when it comes to college. While Jack's convinced that New York is the place to go, Jen isn't so sure she's ready to return there because of unresolved issues with her parents. Jen tries asking Drue for advice on her past, but he's no help.
As Senior Ditch Day arrives, Joey is excited to find herself accompanying Jen on an excursion to New York City under the auspices of attending a college meeting. But it's not long before Joey realizes that they're there for an entirely different reason. Jen is there to meet her estranged father, Theo, where she reveals to him the roots of her self-destructive lifestyle. Meanwhile, eager to infuse their relationship with a bit of spontaneity, Gretchen and Dawson take off on their own road trip. But what starts out as unpredictable fun turns into one debacle after another when they get stuck in the middle of nowhere with a flat tire. Back in Capeside, Pacey and Drue find themselves the only seniors in school on Ditch Day. That evening, they set out for some real fun, drinking at a bar which leads to both of them getting arrested for underage drinking, leaving Pacey in serious doubt as to what his future will hold for him.
Gail throws a baby name shower to try and think for a name for the baby. But it's an experience that throws Joey for a loop when she realizes it's possible that she could be pregnant, and Pacey is nowhere to be found. After a series of false alarms, Gail finally goes into labor and forces the hesitant Mitch to take her to the hospital. While Dawson awaits the arrival of his new sibling, he and Gretchen wonder what their future holds when she considers an out-of-town job. Meanwhile, Jack faces an unexpected situation when he learns that Tobey has fallen victim to a vicious hate-crime and wants to keep it to himself.
As everyone gets ready for this year's senior prom which is held aboard a yacht cruising on the cape, some bad news causes Gretchen to reflect on her life, and Joey worries about Pacey's odd behavior. Meanwhile, Jen and Jack meddle in each others' lives resulting in some interesting prom dates with him being paired with Toby and she being paired with Drue. At the prom, Joey and Pacey confront once unspoken issues after a series of misfortunes incidents, in which Pacey loses his short temper and explodes at Joey saying that he will not be attending any college and resents the fact that she and everyone else is. The festivities cause conflict for Gretchen as she questions her relationship with Dawson after she tells him that she has decided to go back to college and thinks their relationship will not work out. Jen ends up getting drunk and nearly falls off the boat, but is saved by Drue who tells that despite his unwholesomeness, he does care about what happens to her, while only Jack and Tobey are the sole happy couple among their circle of friends.
As the school year draws to a close, Joey and Dawson deal with their respective break-ups, while Jen makes a startling decision about her future when Grams announces that she is selling her house to pay for her tuition. Meanwhile, Dawson has his own decision to make with regards to Gretchen when he wants to be with her for the summer before she goes back to college. But Gretchen refuses when she sees the specter of Joey hanging over Dawson and leaves town without saying goodbye. When Mr. Kubelik from Worthington asks Joey to bring Pacey with her to a party for incoming freshman, which fills the pair with hope that they might be able to have a future together. But it's revealed that Mr. Kubelik wants Pacey to work for the summer on his boat as a deck hand.
As graduation day approaches, Joey has a tough time preparing her commencement speech, and Dawson helps her find some bittersweet inspiration. Pacey wonders if he's going to graduate at all and worries that his last final will be the toughest one. He walks out of it after his teacher makes a rude comment on him, costing him his diploma. Meanwhile, Andie McPhee returns to Capeside for the cap and gown ceremony, and is surprised to meet Jack's new boyfriend, Tobey. Pacey spends some quality time with Andie and decides he must get out of town to search for his feelings. After a friendly talk with Doug about his future, Pacey privately says his goodbyes to Doug, and then leaves town, vowing never to return. Also, Drue temporarily moves into Jen's house after being kicked out of his home by his mother after an argument. Drue then tells Jen that before they both graduate and go their separate ways to college, he convinces her to help him pull a hilarious senior prank for old times sake by setting off the school sprinkler system during the ceremony. But they get caught by Principal Peskin whom forces them to listen to his awful violin playing skills for three hours as their final detention of punishment.
Accepted early to the University of Southern California, Dawson finds his last night in Capeside has arrived much sooner than everyone had originally anticipated. While Dawson looks forward to spending the evening with his friends Joey, Jack and Jen, his father Mitch has other ideas to spend it with him. Meanwhile, Dawson's not the only goodbye Jen has in store for her, as she bids farewell to the house she's been sharing with Grams as she prepares to sell it. Pacey also phones Dawson from Miami to say his own goodbye while Joey says goodbye to Dawson in her own way, with a final goodbye kiss.
Joey is in her 2nd month at Worthington University where she is struggling in her beginners writing class taught by Professor David Wilder who criticizes her first essay about her and Dawson. Audrey Liddell, Joey's brash new roommate from Beverly Hills, proves to be more of an annoyance than a friend with her wild and crazy personality. Dawson, who's continuing his studies at USC with an internship in Hollywood, begins his job on a shaky start when he meets Todd Carr, an arrogant, egocentric, hack film director who gives Dawson a hard time. Meanwhile, Jen pays Pacey a visit, who's lying low as he docks his yacht in Boston Harbor after sailing away the summer. At nearby Boston Bay College, Jen and Jack are invited to their first fraternity party. They persuade Joey to come along with Audrey who seems to get along with Jen and Jack, much to Joey's surprise. Also, Jen meets Charlie, a bass player. She is rude to him, insulting him away, but deep inside feels strongly attracted to him.
After arriving in Boston to visit, Dawson sees great complications in his past relationship with Joey, who decides to drop out of Professor Wilder's writing class. But the line is incredibly long, which takes Joey all day and all the time she had to spend with Dawson, who ends up being guided around the campus by Audrey whom he confides in with his problems. Meanwhile, Jack pushes Jen into talking to Charlie, who works as the campus radio DJ, and after their first date, she ends up sleeping with him. Also, Doug pays Pacey a visit at the Boston docks and tells him about a job he can get for him at a restaurant, called Civilization, in which the chief, Danny Brecher, is a friend of Doug's. Reluctant at first, Pacey eventually gives in and gets the job after his latest girlfriend, Melanie, is forced to pay for their evening out since Pacey has no job or money.
Dawson goes back to Capeside to inform his parents of his decision to drop out of USC and stay in Boston. Mitch reprehends him and tells him he belongs in California, but Dawson's decision is made. Meanwhile, Jack is accepted on the Sigma Epsilon fraternity house and has doubts if he should go because they want him because he would be filling a quota of being a gay member. Joey finds Pacey working at the restaurant and goes pay him a visit on the boat where they have a nice conversation about their current lives. Pacey, bored of just peeling potatoes at the restaurant, has to put up with one waitress, named Karen Torres, and her bad mood in which he later finds out because he got the kitchen job she wanted. Also, Jen and Charlie try to go through 12 hours without sex so they can learn more about each other.
After Mitch suddenly dies in a car accident, Dawson has to handle the funeral arrangements where everybody comes to give him and Gail support as Dawson tries not to breakdown upon his father's sudden death. Gail, unlike Dawson, is not holding up very well and feels sorry for six-month-old Lily, who will never know how her father was like. Everybody, including Joey, Jen, Jack, Pacey and even Grams Ryan try to comfort Dawson in their own way, and Dawson starts to blame himself for his father's death.
With Dawson still staying in Capeside, Joey tries to get his mind off his father in which they end up going to Professor Wilder's book party where Dawson has an emotional twist which makes him storm out of the party. Meanwhile, Jen sees Charlie with another girl and makes a scene out of it, but turns out it was his sister. Embarrassed, she decides to make up for it and bring him a fruit basket, and catches him kissing another girl. Tobey makes a surprise visit for Jack, who gives more attention to his fraternity brothers and he ends up breaking Tobey's heart. Also, Pacey still tries to establish a good working environment with Karen and learns that his boss, Danny, is cheating on his wife by meeting a mystery woman aboard his boat.
Dawson goes to Boston to see a shrink for his anxiety attacks. Instead of calling Joey right away, he decides to go party with Jack and his fraternity friends. Jen decides to get back at Charlie for cheating on her by teaming up with the other girl, Nora, to get revenge. Meanwhile, Audrey's overbearing mother, Kay, arrives from Califoria for a visit, and all she does is drive Audrey insane by judging her and making her feel bad. Joey sees herself caught up in the middle of the mother-daughter argument and makes an intervention in order to save her roommate. Also, Pacey discovers that the woman Danny has been cheating on is Karen when he recognizes a necklace she wears which was in Danny's possession.
Jen helps Dawson go back to the psychiatrist, Dr. Rachel Weir, whom he ran away from. Dawson still thinks that the whole idea of sharing his thoughts with a complete stranger is weird, but he is surprised with how much he learns from it. Back home in Capeside, Dawson has to handle the problem with his father's will, which does not include baby Lily. Meanwhile, Joey is working on a project with Professor Wilder about old love letters written by an obscure writer, and with a little help of Audrey's audition videotape for "The Real World: Ibiza," she manages to catch something not one of the fellow students caught. Also, Pacey confronts Karen about the risks she is taking for having an affair with Danny, but she refuses to listen to him. Later, Karen is hurt when Danny's wife shows up at a dinner party the restaurant holds, and he completely blows Karen off.
Dawson's therapist advises him to go to New Hampshire (where his documentary film of Arthur Brooks is being honored) and take a friend with him since he's been feeling so estranged from them. He takes Jen (who gets heartbroken after finding out that Charlie is trying to reconcile with his other girlfriend, Nora, and not her) and they pretend to be a couple, getting a very romantic honeymoon suite. Meanwhile, Jack brings Joey and Audrey to a frat party and Joey finds out they're only there for the fraternity brothers to score with them. Also, Pacey takes Karen on a non-romantic date and they accidentally sleep together, in which she reacts confused, quits her job, and hits the road.
After going to see a scary movie and feeling completely unsatisfied, Joey, Jack, and Pacey arrive at Grams' house and decide to tell some scary stories of their own. First off, Joey tells how she had a creepy encounter while studying alone at the library on Halloween night. She could have gone to a party with Audrey, who reminded her that a young female student was attacked there not too long ago. Next, Jack tells of how he was spooked while sorting through items in the frat house basement. Third, Pacey's story involves an unsettling run-in he and Karen had while driving on a quiet road one night. It seems a mysterious driver wouldn't be satisfied until he ran them off the road for good. Finally, Grams comes in and caps the night with what she promises to be the scariest story of them all. It involves Jen, the radio station, and someone (or is it something) that gives her a scare.
Pacey offers to cook for the gang on their weekly dinner at Grams house. Jen and Dawson return early and decide to keep their sexual encounter a secret, but they are caught by everyone making out at the door. The dinner goes on in a very awkward way for everyone as Audrey and Dawson worry about Joey, while Jack and Pacey worry about Jen. Charlie later drops by to talk to Jen, causing some tension for Dawson.
Joey and Audrey go out to a nightclub to celebrate both Joey's straight-A grades and the winter break from school. Charlie is also there and he hits on Joey, who turns him down for what he did to Jen. But Charlie doesn't give up so easily and dares Joey to do something wild in which she accepts a dare to go on stage to sing with his band. Meanwhile, Pacey sees himself hanging out with Audrey after he joins her and Joey at the club to celebrate his new promotion when Danny makes Pacey the assistant chef at restaurant Civilization. Also, Dawson and Jen go back to Capeside to visit his mother where they have their first fight over what Dawson will do with his life.
Dawson begins directing Oliver's movie with Oliver playing the lead where Dawson has to deal with Audrey (who took the leading female part) as well as her complaints about Oliver's kissing skills. When Dawson discovers that Oliver has no talent in acting, he must recast the male lead role within the day and Jen comes up with the most unlikely candidate: Charlie. During the filming, Audrey has a crisis and locks herself in the bathroom because she kissed Pacey and felt like she was betraying Joey. Meanwhile, Joey feels conflicted over where to go on with her situation with Professor Wilder, but is called away from him at his out to help out with Oliver and Dawson's film to help Audrey get back on the set so they can finally finish the shooting. Also, Jack is fed up with his frat brothers after the homophobic Eric accuses Jack of making a pass at him in which Jack moves out of the frat house.
In a cross-over continuation of the previous episode, set in real time during a cold winter night of a sudden snowstorm, Joey is robbed at gunpoint and forced to clean out her ATM account by a street mugger at a deserted area of Boston's Downtown Crossing district. But the robber ends up getting run over by a car in a hit-and-run accident, minutes after mugging Joey. Instead of calling the police, she stands by her aggressor, checking up on him and trying to get an ambulance to get him to the hospital after seeing the similarities between him and her own father, especially when Joey meets the guy's estranged wife Grace, and her young, tomboy daughter Sammy in the hospital waiting area.
Professor Wilder ends whatever romance he had with Joey, and refuses to listen to an explanation of why she stood him up the night before by saying it was for the best. Joey is shocked, but not as much as when she spots him at the movies with another woman during an outing with Dawson. Meanwhile, Jen has to interview a band for her radio show, but things aren't as easy as she hoped when she has to fight flirtation at all costs with one of the members of the band, while Audrey does the same with another member. After Audrey refuses to give her growing relationship with Pacey another chance, he goes out with Jack to a gay bar where Jack shows Pacey an inside look at what it feels like being a woman.
Charlie asks Joey to sing with his band at a distant biker bar club, which requires Pacey to give them a ride. Pacey and Charlie hate each other, and it takes a patient Audrey to keep them from going at each other's throats. At the bar, Joey is nervous and isn't well received by the rough audience, until Charlie helps her with a duet. They all end up for the night in a cheap motel where Joey begins to have feelings for Charlie, while Pacey and Audrey escape from their problems with sex. Meanwhile, Dawson, Jen, Jack and Grams drive up to Capeside for Lily's 1st birthday, and Dawson finds out his mother has a new significant other. Also, Jen confesses to Jack that she wants to break up with Dawson after feeling they are not right for each other, while Dawson is conflicted with the possibility of loving Joey again.
Oliver arranges a screening for their movie, which one of the guests turns out to be Amy Lloyd, movie critic for Boston Weekly, whom Oliver secretly invited for the screening and has a quarrel with Dawson. Meanwhile, Joey goes to Jen for advice on her feelings for Charlie, while Jen deals with Clifton Smalls, the new African-American boyfriend of Grams. Audrey tests Pacey's love for her by teasing him about the number of men she has had sex with. Also, Oliver decides to ask Jen out. She turns him down, but he plays her into being curious about him.
On Spring Break, the gang flies down to Florida to party at a beach house owned by Audrey's parents. Here, Audrey and Pacey go through their first relationship test when Audrey's old high school boyfriend, Chris, shows up with tickets for a concert where she is torn with the memories of the past and her present situation. Charlie unexpectedly shows up to try to spend some time with Joey, while Jen spends most of the week in bed suffering from a bad cold, and Jack spends his time getting drunk and refuses to talk about what's bothering him. Meanwhile, Dawson and Oliver are on the road driving towards New York to meet with a film agent who's interested in their movie Dawson spends the time telling Oliver his whole life story about him and Joey with hopes that there lies some reconciliation.
Charlie's band lands a deal for a tour and he asks Joey to go with him, but she doesn't want to leave college in the middle of the semester. Charlie then decides to quit the band and stay with her. But she breaks up with him so he can go with his band on tour. Meanwhile, Oliver and Dawson finally get to New York to meet with an agent. But Oliver ruins the meeting with his brazen obnoxiousness, and Dawson ends their partnership. Also, the restaurant Civilization is sold and an attractive, 30-something woman, named Alexandra 'Alex' Pearl, takes over as the new manager. She promotes Pacey as head chef, but fires Audrey and half the other employees. Pacey tries to get Audrey her job back, but all he gets is an inadvertent kiss from Alex.
Pacey's new boss, Alex, proposes more professionalism in the workplace. Audrey suspects something is going on between Pacey and Alex, leaving the future of their relationship unknown, while Pacey struggles with the growing attraction he feels for Alex. But when Alex shows up at Pacey's apartment and propositions him, Pacey learns that she is just a tease. Meanwhile, Dawson runs into Amy Lloyd, and they end up having sex at her apartment, where they talk about movies. She gives him an old Woody Allen movie and tells him that it's a gift. Dawson finds a movie she directed as a student and wants to see it, but she adamantly refuses. Also, Joey and Jack focus on studies, and while she has problems concentrating at the library, he has to catch up an entire semester and goes back to the fraternity house asking for help, but they refuse. Luckily, Eric shows up at Grams' house with the needed notes to help.
With the end of the semester, Joey and Audrey pack their things and move out of their dorm room. Professor Wilder also says goodbye to Joey before he tells her that he has decided to leave Worthington to try writing novels again. In Capeside, while Audrey hangs out with Dawson, Joey decides to visit her dad in prison, only to find out he was released on parole four months ago. Meanwhile, Dawson receives a phone call from their agent saying that some big producer in Hollywood wants to make something out of their film. But Dawson doesn't know how to break the news to Oliver, whom he has barely spoken since their trip to New York. Alex is still ruling the Civilization like the devil-in-person and fires a waitress. Fed up with Alex, Pacey takes the opportunity of a meeting with investment executives to protest her employment tactics, which pushes her over the edge. Also, Jen and Jack decide to take an adventurous vacation in Costa Rica, but Grams tells Jen that her parents have invited her to spend summer at their new beach house.
Summer is upon the gang and so they move on with their lives to follow their own plans. Joey, back at Capeside, returns to her job as a waitress at the Yacht Club; Pacey gets a new job there as a security guard and runs into Danny Brecher whom has left his wife; Dawson and Audrey are on their way to L.A.; and Jack and Jen to Costa Rica. But a few things change everybody's plans when their flights are delayed. Bessie tells Joey they got an answer from the scholarship Joey thought of applying in France (which Bessie secretly sent in without Joey's knowledge). Also Grams decides to go to Las Vegas with Clifton. Jack meets Eric at the airport, who was just coming back from his hometown where he tried coming out to his parents. Jen tells Jack to go help Eric, as she'll go help herself by going to meet her parents.
During the summer, Pacey and Audrey rocked Los Angeles and spent time with her next door neighbors, the Osbournes, and Jack Osbourne even tags along with them to interview at Worthington. Jen spent her time in New York and got ecstatic to learn her parents are separating. Jack got dumped by Eric, but got over it. Joey spent her summer in Capeside doing a lot of reading, working and romancing. On their first week back at Boston Bay College, Jen is shocked to run into find that Grams Ryan has decided to go back to school. At Worthington, Joey experiences nothing but bad luck when she decides to enroll in an intermediate writing class taught by the liberal, but manipulative and cynical, Professor Greg Heston who does not hesitate to ridicule and embarrass Joey in front of the class with her lack of knowledge of the current book topic. Pacey and Jack move out of Grams' house and Pacey tries to get the perfect apartment, owned by a feisty, punk rock British woman, named Emma Jones, who works as a waitress in the local bar Hell's Kitchen. Also, Dawson is working on a new movie, a horror film titled "Wicked Dead" with him as the assistant director and the hack Todd Carr as director. When he finally gets together with Joey, he is the only one to have remembered her 20th birthday.
After spending their first romantic night together, Dawson and Joey decide not to discuss it, because every time something happened between them they always ruined it by over discussing it. Dawson even shows Joey the set that he's working on which resembles his own house in Capeside. Meanwhile, Pacey starts on his new job as a stock broker which was set up by Audrey's father and during Pacey's first day he deals with his ambitious, but oily and pig-headed boss Rich Rinaldi. At the same time, Jack finally gets himself and Pacey the dream apartment Pacey was chasing so hard to get, with a little deviousness against Emma. During a heated argument with Grams, Jen accidentally meets a very cute guy, named C.J., a fan of Jen's defunct radio show who invites her to a counseling center that he works at. Also, Joey is hired as a waitress as the local bar, Hell's Kitchen, to get some extra cash for herself.
Joey's worst nightmare comes true when she accidentally sends a very personal e-mail she wrote for Dawson to the entire student body. The next morning, Joey's e-mail is the topic of virtually all campus discussions when Professor Hetson cruelly decides to debate it with his students just to see Joey squirm at the talk. Meanwhile, Jack makes an attempt to get to know his cultural professor, Mark Freeman, better, but he pays no attention to Jack. Pacey, while struggling to survive the first days on his new job, closes a very important deal for the firm, which his wheeling-dealing mentor Rich Rinaldi takes full credit for. Eddie, at student in Joey's reading class and whom works as the bartender at Hell's Kitchen, persuades Joey to confront any challenge that Hetson throws and not show any weakness because the stern and misogynistic Hetson thrives on it.
Dawson's former girlfriend, Natasha, (whom Dawson met and dumped during his summer in L.A.) returns as the new lead actress for the movie and now he has to deal with the consequences of dumping her over the phone. The production orders some food from Hell's Kitchen and Joey delivers it on the set, forcing her to see Dawson. Natasha gets angry and jealous when she sees Joey and has Todd fire Dawson by saying she will not work unless Dawson goes. But Natasha soon realizes Joey has hurt Dawson much more than he hurt her. When Eddie confronts Joey about her uncertainty, she decides to "follow an impulse" and kisses him. Meanwhile, Pacey ditches Audrey and goes to a strip club party with his bosses. Audrey runs into him and goes to a party with Jen and Jack, where she gets drunk and almost sleeps with a guy, if it weren't for C.J.'s stopping her. Also, Jack is disappointed when Professor Freeman tells him his wife is pregnant, and later makes a move on Jack.
Heather Tracy, Dawson's movie producer, arrives on the set and threats to shut down production on the film if the lead, Natasha, isn't replaced. The egotistical Todd doesn't do much to save her job and it's up to Dawson to keep the film from being canceled altogether. Back at Worthington University, Eddie has an argument with Professor Hetson over him criticizing Joey's presentation and he storms out of the class. Joey leaves after him, and then she discovers he's not a student after all. Meanwhile, Emma asks Audrey to be the new lead singer of her all-girl punk rock band, Hells Belles, which will perform at Hell's Kitchen. But Pacey continues working late hours and misses Audrey's debut performance. Also, Jack confronts Professor Freeman after he gives Jack's paper a C- which Jack thinks was the result of an argument the previous day.
On Halloween night, Todd throws a costume rave on the sound stage where Dawson thinks he sees the ghost of a famous Hollywood actress whom was murdered, while he also sees Todd and Natasha becoming more friendly. Jen is encouraged by Jack to call C.J., but she thinks he's gay after he shows up at the rave with another guy. Jack has a talk with C.J. and finds out the guy he's with, David, is gay, but not him. But C.J. also confides in Jack that he's not interested in Jen either. Meanwhile, Joey is stuck babysitting for Professor Hetson's annoying and headstrong 15-year-old daughter, Harley. Eddie helps her by taking them to a haunted house, where he and Joey kiss. Also, Audrey breaks up with Pacey at the costume rave after she overhears him talking to Emma that he doesn't love Audrey anymore.
Audrey gets a little too drunk before a concert with 'Hells Belles' band at Hell's Kitchen, and ends up making a scene and trashing the place. C.J., who was there on a "non-date" with Jen, tries to give her a little comfort and end up taking her back to his place. Meanwhile, Jack attends Professor Freeman's book signing and tells him the moment for Jack to make his move has passed as Freeman informs him that he has quit teaching to concentrate on his writing career. Jack then goes to invest his relationship with David, who waited all night long for Jack to show up at the bar. Joey feels bad for not being there for Audrey and has an argument with Eddie. When Eddie comes over to Joey's dorm to hand her Audrey's wallet that was forgotten at the bar, they decide drop their little game and go on a date. Also, Pacey's firm partners go down to New Orleans to celebrate a business deal, and Pacey has a big disappointment when he learns that the girl he's with is a call-girl bought by Rinaldi.
Dawson gets concert tickets for the band 'No Doubt' for the entire gang. Joey asks Eddie to go with her, but she forgets their tickets. But they sneak backstage anyway with a little help from Eddie's father who works as a maintenance man in the building. Jen sets Pacey up to meet Audrey at the concert hoping they'll reconcile. Everything goes well at first until C.J. confesses to Jen that he and Audrey slept together the night before, and he later confronts Audrey about her relationship with Pacey. Pacey learns about it and starts a fistfight with C.J. in which they get thrown out of the concert, as well as Jen, Audrey, Emma, Jack and David just for being with them. At the same time, Dawson misreads his tickets that are for Saturday's concert, and he and Natasha end up in jail after a policeman catches them making out in the parking lot, and Todd has to bail them out.
A big movie star, named Max Winter, arrives on the set to act with Natasha, and the flirting between them upsets Dawson. Pacey takes Emma to an office party where she finds out that Pacey is using her to win a contest among the office employees to see who brought the hottest date. Meanwhile, Joey has an upcoming Hetson final and Eddie offers his place for her to study. In the morning, they talk and end up having sex, which causes Joey to be late and she ends up missing the exam. Professor Hetson refuses to let Joey take a make up test and outright gives her an 'F'. Later that evening, Hetson comes to the bar and immediately starts an argument with Eddie where, in a very cruel tone, he tells Eddie how much he despises a loser like him taking up Joey's time. The hot-tempered Eddie falls right into the trap by punching Hetson in the face, and he gets instantly fired from Hell's Kitchen for it. Admired by Eddie's actions and stand against the mean Professor Heston, Joey then tries to cheer Eddie up and admire him for his noble act by taking to a local ice skating rink where they declare their love for each other.
Dawson goes back to Capeside to celebrate Christmas and brings Natasha and Todd with him where Dawson can't get past the fact that he saw Natasha and Max together, and Todd's drunkenness bothers Gail. Joey also arrives back in Capeside with Audrey, where Eddie later arrives with a Christmas tree to celebrate. There Eddie meets and has an argument with Joey's father, Mike Potter, who worries that Eddie might not be good for Joey since he's now unemployed and doesn't go to college. Pacey also comes back to spend time with his brother Doug who does not like the expensive gifts and constant, lavish spending Pacey is doing after making a lot of money at his stock trading job. The gang, as well as Jen and Grams, gather to have Christmas dinner at the Leery household which goes disastrously wrong where a drunken Todd makes an embarrassing thanks, but not as embarrassing as Audrey's, whose drinking problem has gone so out of control that she lashes out on everyone, and wrecks Pacey's new car.
During a typical five-day work week, Joey is incessantly trying to reach Eddie while dealing with Harley Hetson showing up at Hell's Kitchen every day after cutting school. When Harley persuades Joey to see Eddie, she is devastated after finding out that Eddie has moved out of his apartment without saying a word. But Joey manages to persuade Harley to behave like an adult, and she also finally stands up to the intimidating Professor Hetson to help him look after Harley once in a while. Meanwhile, Pacey begins skipping work by hanging out at the Boston Aquarium with Emma. But any romance between Pacey and Emma is quashed when Rich Rinaldi buries Pacey with more paperwork, making him miss his lunch date at the aquarium with Emma. Jen starts working as a peer counselor with C.J., but her personal interests get in the way of her work. Jack and David both get tested for HIV which leads to them talking about their sexual pasts. Dawson and Todd fly to Los Angeles after photography on Todd's movie, "Wicked Dead" finally wraps up. But Heather Tracy and the executive producer, Larry Newman, want Todd to re-shoot the entire ending. After Todd refuses, due to his pride and ego, he gets fired and Dawson is ordered to step in as director. Also in L.A., Audrey goes back to her roots by hanging out with her party-loving friend Jack Osbourne.
Harley tries to encourage Joey to make up with Eddie after they find him now living with his parents in nearby Worcester, and even gets him to return to her with a made-up story about Joey being pregnant. Meanwhile, Audrey returns from L.A. with a more positive attitude. After apologizing to her friends, Emma takes Audrey back in the band Hell's Belles for a big concert. But Audrey cannot stay away from liquor in which she performs drunk, and passes out on stage, and Emma fires her from the band. Meanwhile, Pacey is invited by Rinaldi to an exclusive party for the best stockbrokers and gets a promotion of handling a mysterious account led by the shady pharmaceutical entrepreneur Roger Stepavich to handle the client's major pharmaceutical company. All is well until a mysterious woman tells Pacey that all that good might have some bad, which raises suspicions on Pacey about Rinaldi's true intentions towards him.
In Los Angeles, while directing re-shoots on "Wicked Dead", Dawson finds his authority questioned by Heather Tracy when Natasha refuses to do a nude scene. Frustrated in this work, Dawson (at Natasha's advice) resorts to an aggressive, Todd-like attitude to get the crew to listen to him. Meanwhile, Joey is unable to say good-bye to Eddie, who is moving to California to register at a college. She convinces him to help her take Audrey to a rehab clinic in Los Angeles, and the three of them, plus Bob, drive cross country where the four quarrel with each other. At a gas station, Audrey steals their car, forcing Joey and Eddie to walk, and they manage to work out their differences. They find Audrey in the parking lot of a bar and save her from an attempted rape by a guy she met there. Back in Boston, Jen and C.J. set a lonely Grams up with C.J.'s Uncle Bill, who turns out to be quite randy.
In Los Angeles, Dawson visits Audrey at the rehab clinic where he spots a big time film producer, named Toni Stark, and follows her into a therapy session hoping to talk to the woman who'll direct Dawson to better contacts. Meanwhile, Pacey throws a party at his place to celebrate his new success at his job as well as purchasing a new super-sized TV set and is surprised when Joey, still sulking over the departure of Eddie, lets loose by getting drunk and setting up a spontaneous game of spin the bottle. Jen catches the reformed alcoholic C.J. with a drink which leads to them arguing, and making up by having sex for the first time. Also, Emma tries to stay in the country to get her green card by courting a stoner to marry her until Jack offers to marry Emma. But in the end, Emma decides that it's not worth it and decides to leave.
After agreeing to pose as Pacey's date at a business party, Joey demands to be taken home. Pacey makes a quick stop at a local K-Mart to buy some snacks and condoms for another date for later that night, and they accidentally get locked inside the store. They're forced to spend the night there and talk about their friendship and relationship, past and future, which eventually leads to a kiss.
Professor Heston orders Joey to baby-sit for Harley to make sure she does her homework. But Joey ends up serving as relationship counselor when she finds Harley's boyfriend, Patrick, hiding in the house and he starts to drool over Joey. Meanwhile, Dawson pays a visit to his past when he's asked to speak on Mr. Gold's class at Capeside High about how it is to be working in L.A. Dawson has a student, named George, show him his movie in which he realizes that he's moved on from the teenager he once was. Pacey also returns to Capeside when his father is admitted to the hospital after suffering a heart attack where Pacey has an argument with Doug about the way Pacey's been treating the family by shutting them out, and resents the new lifestyle Pacey has.
Joey agrees to be Pacey's temporary secretary over his recent promotion. But they both have second thoughts when their mutual jealousy leads to disaster in the office over a reporter, named Sadia, the same woman whom met Pacey at the office party (in the 'All the Right Moves' episode), as well as Joey not getting along at all with the pig-headed and callous Rich Rinaldi. Meanwhile in Los Angeles, Dawson sells his idea for a coming-of-age movie, but when the studio heads Heather Tracy and Larry Newman want to change the movie into a teen sex film, Dawson must decide if he should take the lucrative deal or stick with his original concept. Also, an open-minded Grams is the intermediary that brings Jen and C.J. back together.
Dawson asks Pacey to help him invest for his first independent film and then returns to Capeside to write his next script. But Gail asks Dawson what will he do in case his plans of becoming a successful director fall through. Meanwhile, Pacey escorts Joey to Harley's school dance where they have a perfect time despite Harley's date, Patrick, picking a fight with another guy. There, Joey tells Pacey she can't have anything to do with him because Eddie is back from California during a break before he starts college in the fall. Also, Grams tells Jen she has been diagnosed with having breast cancer, and Jen sees her entire world fall apart with the possibility of Grams's death.
Audrey returns to Boston from rehab in L.A. and tries to make peace with everyone while the gang see their relationship problems exposed to a large audience when they all become patients of Dr. Drew Pinsky and Adam Carola's counseling center benefit at Boston Bay. C.J. is trying to find out why Jen inadvertently dumped him that very morning, while Eddie wants to know why is Joey opposing to have sex with him, while David thinks Jack is flirting with another guy. All and all, Jen ends up walking away from her hosting duties, leaving Audrey in charge. She tells C.J. about Grams' disease and C.J. assures he's there for her. Joey finally gives in and asks Eddie back to her place. But David and Jack don't have happy ending for David refuses to believe Jack was just being nice and asks for some time off.
Joey aces Professor Hetson's final exam and ends the semester with a C+, and Joey is finally relived that her ordeal with Hetson is over. However, she decides she wants him as her advisor after she chooses English as her major. Eddie proposes they go backpacking through Europe before going their separate ways to college. Reluctant at first to jump so suddenly on such an intense trip, Joey decides to go, only to find a goodbye note from Eddie, this time for good saying that she deserves someone better than him. Elsewhere, David finally breaks up with Jack, who ponders if he was only with David to prove to himself that he could hold a steady relationship. Meanwhile, Pacey continues dating Sadia and selling stocks. But things change drastically, first when Sadia leaves him by returning to her fiancée. Then the biotech stocks that he and Dawson were investing in go bankrupt. Pacey then asks Rinaldi to borrow some money, but the cold-hearted Rinaldi refuses. Frustrated and angry, Pacey finally snaps and punches Rinaldi in the face, who instantly fires Pacey.
Pacey, now jobless and penniless, returns to Capeside where Dawson invites him to be a producer on his autobiographical film. Pacey accepts, but can't work up the courage to tell Dawson that all his money is gone. With classes at Worthington over, Joey says goodbye to Audrey who has to stay behind to attend summer classes to make up for her absences, with Jack Osbourne tagging along. Joey also returns to Capeside to see Dawson where they have minor argument with about how she wanted him to be the most significant person in her life and somehow he became her only one night stand. Back in Boston, Jen invites her mother, Helen, over to Grams' house where she wants her to tell Helen about her cancer. While introducing C.J. to Helen, Jen witnesses C.J.'s Uncle Bill storm into the house and yell at Grams, revealing everything by saying that she shouldn't give up on her life just because she has cancer. Jen suggests that they all move to New York to live with Helen. Also, Audrey decides on a low-key change for herself by playing an old-fashion acoustic guitar at Hell's Kitchen, and Pacey finally tells Dawson about losing all his money in his poor stock investments.
As Dawson abandons his lifelong dream of becoming a filmmaker and works to pay off his huge credit card debt, Joey decides that Dawson must realize his dream, and rallies everyone she knows to help him begin production on his movie, which is the autobiography of his life. Joey forcibly recruits Harley and Patrick to play the roles of Joey and Pacey, and George volunteers to play Dawson, while Audrey volunteers for the role of Miss Jacobs. Gail even calls Todd Carr to assist with the production and Doug Witter for security, whom is now the acting sheriff since Mr. Witter is too sick to work anymore. Meanwhile, Pacey is newly inspired to raise the funds that are needed by going to various local businesses to raise money and at one meets a crush from his past, Christy Livingston. As filming wraps, Jen, Jack and Grams say goodbye to everyone as they leave for New York City where Jen and Jack transfer to NYU. Joey acts an a mentor to get Dawson and Pacey to make up while she finally achieves her life-long dream of going to Paris.
The year is 2008. After five years, the gang returns to Capeside for a reunion and wedding after taking different paths in life. Joey is a successful book editor living in New York with her current boyfriend Chris. Dawson lives in Hollywood and is a successful executive producer of his autobiographical TV series, 'The Creek.' He is still single, but has not forgotten the love of his life. Pacey is now the manager to the re-opened restaurant, The Ice House, but still continues his brash lifestyle of dating older women. Jack is now a teacher at Capeside High and dating Pacey's brother Doug, now the sheriff, who is still closeted. Jen lives in New York with Grams and runs an art gallery in SoHo, and is now the mother of a baby girl, while Audrey has gone off to Europe on tour with a band. They all (sans Audrey) meet at Pacey's restaurant, and after a little too much wine they all start bringing back ghosts from the past. They all get dressed and ready for Gail's wedding, and between old memories and new bruises (from Pacey, who was beaten up by some married woman's husband), Joey tries to balance having the two men that changed her life around her. Suddenly, Jen faints and is taken to hospital, where Grams reveals that she suffers from a lethal heart condition. Jen is dying...
With Jen in the hospital, the gang tries not to be too sad about it. Dawson helps Jen make a video for her infant daughter, asking her to never stop loving and dreaming. Jen also asks Joey as her last wish to end the chasing and running and to settle down. Jack tells Jen that she's his soul mate and asks to raise baby Amy for her. Jen finally passes away and while mourning the death of their close friend, the gang has to move on. Doug tells Jack he's willing to spend his life with him and wants to help raise Amy. Joey breaks up with Chris over the phone while she tries to decide whom she will choose: Dawson or Pacey. After Jen's funeral, Pacey suddenly tells Joey that she's "off the hook". Pacey explains to Joey that despite his endless love for her, he can't hold her back any more. Since both Joey and Pacey had troubled and painful childhoods and adolescence's (Joey with her mother's death from cancer and her father's imprisonment for drug trafficking, and Pacey with his outrageously neglectful and abusive parents). But his point is that, as much as Joey wanted, all her life, was to get far away from Capeside and see the world, Pacey seems forever destined to be stuck there just like his alcoholic loser father, and grandfather, and so on. Before returning to New York, Joey sits with Dawson and confesses that even though they may never be together, he and she are soul mates and nothing should ever change that.