- Audience-Alienating Premise: Incest, statutory rape, pedophilia, parental neglect and abuse all rolled into one.
- Fridge Brilliance: Chad threatens to use his "government-issued revolver" on Todd early in the film. At first, it seems like an error by the filmmakers, as the US Military hasn't issued revolvers in almost a century. Then you find out that Chad was only pretending to be a Marine.
- Hilarious in Hindsight: Leighton Meester portrays an apparently, quirky but actually a complete jerkoff of a bride-to-be that cheats on her husband-to-be with her brother and in the series finale of her show, Gossip Girl, a half-brother and sister (they share a brother) get married.
- Squick: Chances are, something in this movie will make you want to throw up or take a shower. Or throw up while taking a shower.
- Unfortunate Implications: As Nathan Rabin of ''My Year of Flops'' pointed out, Donny and McGarricle's student-teacher sexual relationship is treated like the ultimate teen fantasy, complete with Donny being cheered on by the whole school assembly when he's discovered in the act. So the implication is sexual abuse of young boys isn't evil pedophilia, it's a blessing every guy would want.
Rabin: Imagine this scene with the genders reversed and you have easily the creepiest scene in the history of American mainstream comedy, and that includes Freddy Got Fingered.
- The Woobie: Todd.
- WTH, Casting Agency?: James Caan and Susan Sarandon, most especially.