Philip mistakes Will for Carlton accidentally several times and offers to pay for Will's Homecoming dance expenses, causing Will to become paranoid that he is becoming exactly like Carlton and totally living off of Uncle Phil's help and money. Will decides to secretly get a job at a pirate-themed restaurant to pay for the Homecoming expenses himself.
- Acquired Situational Narcissism: When Tina expresses attraction for him, Carlton rebuffs her as he should; however, her attention does give him an ego boost and when she develops feelings for Will instead, Carlton ends up trying to keep her attention on him.
- An Aesop: You don't need to feel guilty about needing help.
- Armor-Piercing Response: When Phil finally chews out the waiter that has been hassling him.Phil: You are the most rudest, most incompetent waiter I have ever met.
Will: [removing his disguise] I'm not a waiter. According to my uncle, I don't even have a job! - Cassandra Truth: Uncle Phil initially does not believe that Will got a job, even grounding the latter for "lying" to him. However, Phil does realize his mistake after Will reveals himself at his job.
- Fish out of Water: Deconstructed. Will is so comfortable with his Philadelphian Blithe Spirit tendencies that he tries to defy this trope wearing off as it realistically tends to do.
- Idle Rich: Will worries that he is becoming one of these and that it will destroy his capability and self-image. While the concern in itself can be a legitimate one, he ends up going too far trying to avert it.
- Leaning on the Fourth Wall: When Philip questions Vivian believing Will's claim that he got a job, he says she would believe him if "he was a big rap star whose album just went platinum".
- Mistaken from Behind: Uncle Phil approaches what is seemingly Will from behind in order to initiate reconciliation; however, this person ends up being another black man wearing the pirate work costume, and to make matters worse, Phil's familial style of speech ends up sounding like a romantic proposition to a stranger.Waiter: What did you say, pervert?!Phil: Oh, I'm sorry, I...Waiter: This is Treasure Island! Now, Pleasure Island is down the street.Phil: I'm sorry, I thought...Waiter: Oh, I know what you thought. But in case you haven't noticed, the parrot is sitting on my LEFT shoulder!
- Oh, Crap!: Phil when Will reveals himself as the waiter. Not only was he wrong about Will having a job (and wrong to ground him when he told the truth), but he spent several minutes basically insulting Will to his face.
- Paper-Thin Disguise: Will's costume at the restaurant includes an eye patch and a fake beard, though it's still clearly him. However, the family doesn't realize it's him until he tells them because a) he furthered the disguise by talking in a funny accent, and b) the family thought he was at home and weren't looking for him.
- Precocious Crush: Ashley's friend Tina develops one on Carlton and later Will. Them being around five years older than her wouldn't fit if they were all adults, but since she's in junior high and they're in high school, it fits.
- Self-Made Man: Discussed Trope. Uncle Phil admits to Will that, while he has worked hard to get where he is in life, he's also had other people open doors for him along the way. He's also worked hard to open doors for his children, Will included, and he sees no shame in choosing to walk through them by accepting help when it's offered.
- Shirtless Scene: Carlton is seen without a shirt when he comes out of the pool and meets Tina, showing that despite Will's frequent teasing about his appearance he is actually quite muscular.
- Troll: While disguised at the restaurant, Will takes every opportunity to insult Phil and Carlton.
