Will reluctantly takes Nicky to the mall to see the child-hero Dougie the Whale. When Dougie starts yelling at the stage hands, Will talks to Dougie to behave for the children.
While on a double date the girl Will wants, kisses Carlton. This results in a wrangle. Meanwhile, Philip and Hillary try to teach Ashley to drive a car.
Will and Carlton play poker with Jazz but think he is cheating. To get even with Jazz, Will and Carlton make up a story about their witnessing a murder and being in a witness protection program.
Philip and Vivian once were on Soul Train and are invited again for a special show. Vivian is very enthusiastic about it, Philip however doesn't want to go.
While Will and Lisa are on a date, another guy starts to pick on them. Lisa steps in and uses self defense techniques to get rid the heckler. Will is embarrassed and takes tae kwon do lessons.
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.
The guys are throwing a bachelor party for Will. On the way, Will, Carlton, and Jazz get stuck in an elevator. They recall past events for each of them, shown in flashbacks.
