Will's love affair with a superstar singer, Michelle Michaels (Stacey Dash), is threatened when he meets her handsome former lover. Will learns that glamorous flings are not fulfilling as meaningful relationships.
Will begins a love affair with Michelle Michaels, a famous pop singer and begins to develop real feelings for her. Will's fling with Michelle causes him to stand up his family when they plan a surprise birthday party for him as well as Jazz and another friend who had planned to watch a boxing match on the weekend with him. At the boxing match, Will is crushed to see Michelle kissing a male model that she had met and she calls things off with him as she wants nothing more than a fling and fun since she is terrible with relationships when Will injures the model during a scuffle. Phillip helps Will realize that he is simply in love with the lifestyle that comes with dating a rich girl he can mooch off of, not being in actual love with her.
- Will Smith as Will Smith
- James Avery as Philip Banks
- Daphne Maxwell Reid as Vivian Banks
- Alfonso Ribeiro as Carlton Banks
- Karyn Parsons as Hilary Banks
- Tatyana Ali as Ashley Banks
- Joseph Marcell as Geoffrey Butler
- Alan Smith as Rick
- David Bertolucci as Mike