|Airdate||April 29, 1991|
|Written by|| Jeff Pollack|
|Directed by||Jeff Melman|
Working it Out
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 (Tevin Campbell), 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.
On the date, Will and Carlton talk to T privately after tricking Ashley away and discover that the date is also his first as he's never had time for a girlfriend between touring and school. At home, Phillip tells the family that he knew one day Ashley would start dating boys but didn't think it would happen so early, realizing that she's growing up. Will watches Ashley fixing her hair in the mirror and thinks back to when he taught her to rhyme upon his arrival in Bel-Air, also realizing that she is growing up too.
- Will Smith as Will Smith
- James Avery as Phillip Banks
- Janet Hubert as Vivian Banks
- Alfonso Ribeiro as Carlton Banks
- Karyn Parsons as Hilary Banks
- Tatyana Ali as Ashley Banks
- Joseph Marcell as Geoffrey Butler
- Tevin Campbell as Little T
- Ron Fassler as Lee Cohen
- Carlton's first crush was Tootie from Facts of Life
- Will says that Ashley is 9 years old in "Bang the Drum, Ashley," but she is turning 12 years old in this episode.
- Will (after Little T has kissed Ashley): Look. I'm tellin' you, Uncle Phil, he kissed her right on her mouth.
- Carlton: It was more on the cheek, Will.
- Will: Yeah, yeah, yeah, yeah, but he was aiming for her mouth and he missed. The kid is not only aggressive, but he's inaccurate and that's a dangerous combination.
- Carlton: I just don't think it's healthy that Ashley's so boy-crazy. I mean, shouldn't she be playing with those toy ponies with the pink hair?
- Philip: Carlton, it's just puppy love. Don't you remember your first crush?
- Carlton: Yeah, it was Tootie on "The Facts of Life."
- Will: Wait, you had a love thing for Tootie? When'd you get over it?
- Carlton: What do you mean, get over it? I'd still love to meet her someday. I wonder what I'd say.
- Will: How 'bout, "Hello, Tootie. I'm Fruity"?