Vivian goes away to Berkeley for the weekend, leaving Hilary in charge. When Will steals the car keys to go to the pool hall, and winds up losing his money and the car to a hustler, Philip must go down to rescue him. There he acts like he's never played pool before and lets the hustlers win. They then play again with Philip's signature cue named Lucille for $100 a ball in which Geoffrey gives to him. He then greatly wins over the hustlers (totalling to $900) and gets the car back. Hilary acts as a tyrant to Carlton and Ashley when she is left in charge.

Ashley's birthday is nearing and when the family asks her what she would like for her birthday, she shows them a picture of Little T, the popular teen singer. 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. They find out that all the things they heard about him were false and let them continue on with their date. At the house, as Ashley is adjusting her hair, Will thinks back to the time he taught her how to rap and how she is already growing up fast.