Jazz asks Will the favor of taking his sister out on a date after she moves into town, Will turns it down until Jazz introduces the two. Will takes her on a date and learns that she has her whole life planned out for the two already.
Geoffrey's old employer Lord Fowler and his daughter come to the Banks' house for the weekend. Will wants to use the car to go to a Ziggy Marley concert in Nevada, Philip and Viv won't let him so he makes a proposition to be on his best behavior for the week. Lady Penelope winds up not being what Will thought she was.
One of Vivian's students, Kayla Samuels comes over for dinner and Will tries to impress her but fails. It upsets Will that he fails so they next day they have an argument but wind up liking each other. Will starts taking time away from her studies and Aunt Viv tells him to cut back on seeing her so she can have a good future ahead of her. Vivian winds up lecturing Kayla and revealing things about her struggle to be successful.
Vivian goes away to Berkeley for the weekend, leaving Hilary in charge of the house while Philip is at the office. Will steals the car keys to go to the pool hall he winds up losing his money and the car to a hustler. Philip goes down to the pool hall to claim the money back, playing the hustler.
Will makes a bet that Carlton wouldn't last a weekend in Jazz' neighborhood, Compton. Carlton starts to fulfill the bet, by not only fitting in, but getting along with the guys in "The Hood". Will has to find a way to stop him from going to MacArthur Park at night, to "Hang with the crew".
Ashley's birthday is nearing and when the family asks her what she would like for her birthday shows a picture of a boy, Little T. Hilary knows T's agent so she has him come to Ashley's birthday party to perform a song for her. They hit it off and set up a date for the next day. Will and Carlton disagree with the date, so they decide to follow them on their date.
Hilary lands a new job as an assistant to an actress, Marissa Redman. Ms. Redman turns out to be completely bossy. Will surprises Hilary with Jazz in the office and Marissa takes a liking to Will, wanting to bring him to a restaurant opening, she puts Hilary's job on the line if she can't set the date up. Will will only do it if Hilary goes on a date with Jazz.
Philip and Vivian take a weekend vacation and leave the kids home alone, Hilary and Carlton set up a video shoot with Bell Biv De Voe in their house, and then everyone must rush to clean up after Philip and Vivian decide to come home early.
Will gets lucky at a fundraiser and wins some money. When Will doesn't follow the club's tradition, it starts rumors about the Banks family. Ashley is too young to go to the fundraiser, so she and Geoffrey set up their own poker night.