During a sleepover, Will tells Ashley and her friends a story about his first day at Bel-Air Academy.
This episode provides examples of the following tropes:
- Big Man on Campus: Will quickly becomes one upon entering Bel-Air Academy, causing tensions to grow between him and Carlton.
- Chafing Against the Dress Code: Will is adjusting to prep school and the uniform of navy blazer, button-down shirt, and tie. He first tries to wear the neck tie as a headband, claiming the rule book doesn't say HOW the tie should be worn. Seeing that the blazer is lined in a bright red print, he wears it with the liner facing out. The administration appears to just give up and he wears it like that until graduation.
- Chewbacca Defense: Will engages in this to try to justify vandalizing the Alumni Desk, putting forth that the academy's inaugural students were somehow worse than him by writing on the desk when it was new, while it was old when he carved into it.
- Ned Fellows engages in this during the meeting as well via Feigning Intelligence about Will's less well-off background, arguing that where Will grew up, "bad" means "good".
- Framing Device: Will's first day at the academy is told through a "scary story" he tells Ashley and her friends.
- Kilroy Was Here: Will decides to leave his mark on the school by carving his name on the Alumni Desk, landing him in very hot water.
- New Transfer Student: The episode focuses on Will's introduction to Bel-Air Academy.
- Oh, Crap!: Will's reaction to learning that Bel-Air Academy is an all-boys school.
- Rushmore Refacement: In addition to carving his name on the Alumni Desk, Will daydreams about his picture up on the wall along with those of the academy's inaugural students.
- Title Drop: Phil angrily declares "Day damn one, Vivian. Day. Damn. ONE", upon hearing about Will getting into trouble on his first day in his new school.
- Undying Loyalty: Will gets saved at the end by the other boys at the school (sans Carlton) threatening to leave, and take their wealthy parents' money with them, if Will gets kicked out.
- Whole Episode Flashback: The episode covers Will's first day at Bel-Air Academy which occurred a few months before the present day.
- Would Rather Suffer: Will makes clear to Carlton he's not interested in having his friends.Will: You just don't get it, do you, man? I don't want your friends. All right? If I woke up one morning and I had all of your friends and I was an Alligaroo and I wore those cute shirts with the little horses on them, I'd jump off the Empire State Building and hope to catch my eyelid on a nail.
