Ashley's birthday is right around the corner, and for her special day Hilary and Will have arranged for her to meet her latest crush, a boy singer named Little T. At the party, Ashley is humiliated first at Geoffrey who shows up as a clown, then at Will who tries and fails to get her friends involved in a dance game, then at Carlton who shows up as a magician. Suddenly, Little T shows up singing Happy Birthday to the birthday girl, who promptly faints. When she comes around, he and Ashley really hit it off. He asks her out and they start dating. Little T's agent makes it known that while his client is on tour, he has a lot of girlfriends. Will and Carlton follow her to the restaurant to see how things go. While Ashley is in the restroom, they confront Little T about what his agent said, and admits that this is, in fact, his first date. At home, the family admits that they overreacted and that they have to face up to the fact that Ashley is growing up.
—Jerry Roberts <armchairoscars@hotmail.com>