Philip and Vivian tell the family they are expecting a baby. Hillary is expected to move out to make room for the baby. Ashley wants to fit in at a new school so she dresses like the girls Will is interested in.
When Philip backs out of taking Vivian to Lamaze class, Will reluctantly offers to be her coach. Will meets a single pregnant woman who is a sportswriter. She invites Will to attend a game with her, where she goes into labor.
Carlton is upset when Paula breaks up with him. She then pursues Will and they begin to date. After getting the picture of an ultrasound from the doctor, Philip & Vivian ask Geoffrey to hid it so they do not find the sex of the baby.
In an attempt to get back at Geoffrey, Will and Carlton give him a fake lottery ticket and trick him into thinking he won $26,000,000. As a response, Geoffrey quits and the boys must convince him to come back.
Will wants to take the next step in his relationship with his current girl Monique, but she is an old fashion girl and wants to wait until marriage. so him and jazz get together to set up a fake wedding. Monique, thinking they are married, is now willing to go all the way, saying that will is a good and honest man. will Will be the man and take her, or will he man up and tell the truth?
Princeton University starts talking to students at Will & Carlton's school about admissions to the university. Will is accepted, but Carlton is not. At night, Carlton has a vision of his guardian angel - Tom Jones.
Will is run down with work, school, and his girlfriend, and has trouble staying awake. He decides to take amphetamines to help him. Carlton asks will for vitamins and Will accidentally gives him the uppers. Carlton ends up in the hospital.
Will's friend Keith, a comedian from Philadelphia, visits Will and the Banks family. His sense of humor tickles Will's funny bone, causing Will to think that a career in comedy might work for him, too. Meanwhile, Vivian is away and Phillip demands the attention of his children in her absence.
Philip and Vivian are celebrating their 25th wedding anniversary and the others put together a scrapbook. This is a flashback show with clips from the previous seasons as the scrapbook is put together.