It's Ashley's birthday and she is going to have a party. Will thinks he is helping by getting Geoffry to dress as a clown. Giving the family, minus Ashley, a good laugh dressed in the clown outfit, Geoffry is less than excited about his part at the party.
Hilary states she has the perfect gift for Ashley's birthday. She is friends with Ashley's teen idol, Little T, who is a young singer. Hilary says she could talk to his agent and get Ashley tickets to his show. Will, Vivian, and Philip think it would be wonderful if Hilary could talk to Little T's agent to get him to come to the party.
During the party, Little T shows up and thrills Ashley and her friends by singing Happy Birthday to Ashley. Ashley faints when he finishes singing.
While in the kitchen, Little T asks Ashley out on a date. Vivian and Hilary are thrilled but Philip, Will, and Carlton are against the idea.
On the night of Ashley's date, Philip sends Will and Carlton to spy on her. After talking to Little T, Will and Carlton realize he is an innocent who just happens to like Ashley. As Will is walking up the stairs to go to bed, he remembers Ashley the first time he taught her to rap and how she is growing up.