After learning of Ashley's Celeb Crush on Teen Idol Little T and finding out that Hilary has connections to his agent, Will arranges for the singer to come to Ashley's 12th birthday party. However, when Ashley and Little T hit it off start going out on dates afterward, Will and the Bankses must come to turns with the fact that the baby of the family is growing up.
This episode provides examples of the following tropes:
- Amazingly Embarrassing Parents: Aunt Viv makes a huge deal out of Ashley's first date, getting a camcorder out and trying to have her daughter do multiple takes of walking into the room in her outfit.
- Will of all people ends up having a non-parent version of this trope, when he does a long dance routine at Ashley's party. While it may be "hip" for high schoolers, the middle schoolers at Ashley's party aren't impressed. He and Carlton follow that up with showing up at Ashley's date to threaten Little T.
- Broken Pedestal: Actually Averted with Ashley and Little T, as he turns out to be a legitimate down to earth 13-year-old who wants to date Ashley to get a break from the stresses of his music career and fame.
- Celeb Crush: Ashley's crush on singer Little T is what drives the episode's plot; Carlton is revealed to have a crush on Tootie from The Facts of Life.
- Celebrity Is Overrated: Little T is shown to be a level-headed guy who wants to go on dates like a normal teenager to get a break from his otherwise insanely busy schedule.
- Chick Magnet: Little T appears to be this, especially from the perspective of his manager, who makes him out into a straight-up Kidanova. However, Little T later states that his manager lies all the time and that in reality, while he may have lots of female fans, he's never had the opportunity to go on an actual date before.
- Consummate Liar: Little T notes that his manager lies all the time about his prominence in the film industry, although it's easy to tell given his obsession with telling stories about making hilariously mundane changes to famous film titles, like going to Pretty Woman from "Attractive Woman".
- Dreaded Kids' Party Entertainer Job: To his great chagrin, Geoffrey is forced to dress up as a clown to provide the entertainment at Ashley's party. He barely stays in character and the kids are immediately repulsed by him.
- Faint in Shock: Ashley's reaction upon meeting Little T.
- Hypocritical Humor: Carlton brushes off the things Ashley says about her crush on Little T, saying they are only juvenile feelings. However, he immediately reveals that he not only had the same type of Precocious Crush on Tootie Ramsey, but still has it, and ends up reacting the exact same way as Ashley when Will mocks him for it.
- Puppy Love: It's made quite clear that the attraction between Ashley and Little T isn't anything more than the standard butterflies for two preteens, though that doesn't stop Uncle Phil, Will, and Carlton's protective instincts from kicking in immediately.
- My Sister Is Off-Limits: And cousin in Will's case. Both he and Carlton are none too excited about Ashley going out with Little T, and are quite happy to follow Uncle Phil's orders to follow the two of them to the site of their date, where they give a grilling to Little T. Will starts coming around to it by the end of the episode though, however reluctantly.
- Starstruck Speechless: After going on a whole monologue before her party about what she might say to Little T should they ever meet, when she does come face to face with him at the party, Ashley responds by fainting.
