Will, in an attempt to impress Lisa, makes a photo of Jay Leno by night and sells the picture to an editor. However, Will doesn't know the editor works for a sleazy gossip magazine and ends up being sued for libel by Jay Leno.
Lisa tells Will is OK if he wants to go out with his friends one night and she will go out with her friends. They each lie about what they are going to do, and happen to both go to the same party. Worse, they find Ashley at the same party.
Will finds out what it is like to have a woman in his life that controls things. Also, Will lands a part in a soap opera and begins to see himself as a major star, spending money to fit his new status.
A family friend visits Philip. He asks WIll to do something illegal and Will tries to find a way to avoid the issue. Carlton and Hilary try to find a match in online dating and end up being matched with each other.