* {{Anvilicious}}: The scene and speech at John's birthday party.
* {{Fanon}}: Fans seem to agree that Beth is Bisexual.
* FanPreferredCouple: Despite Kate ending up with Scott, most fans don't ship her with him. Instead most fans prefer to pair Kate with Beth. This is usually due to the fact that they actually kiss, Beth often being interpreted as bisexual, and the chemistry between the two actresses. There's not much fanfiction about the film, but most of it is Kate/Beth.

* FridgeHorror: The girls trying to work out who Kate is by asking if she took a year off last year to go into rehab, then for bulemia or fat camp. Creator/BrittanySnow actually suffered from eating disorders in high school and appears fine - if someone had genuinely just come out and asked those things, well, it sounds really insensitive. Good thing Snow's ever the professional.
* HilariousInHindsight: The Tucker brothers, John and Scott. John is hugely popular while Scott is widely ignored. Nowadays Penn Badgely is a popular actor while Jesse Metcalf has diminished in popularity.
** Until the ''Series/{{Dallas}}'' reboot came out that is.
** Creator/BrittanySnow played the young Lily Rhodes on ''Series/GossipGirl'' (and for its planned but not picked up spinoff). So in other words, Dan Humphrey had a crush on his stepmother.
* HollywoodHomely: The audience is really supposed to think that Brittany Snow is any less attractive than her equally beautiful mother played by Jenny [=McCarthy=]
* JerkassWoobie: By the time John's humiliation rolls around, it isn't as fun to watch as initially expected. The "Will you be my girlfriend?" scene has a vicious case of DramaticIrony.
* LesYay:
** The practice kiss between Kate and Beth.
** Beth calling Kate's mom hot.
** The other girls blatantly gawk at Kate when she dresses in lingerie to video chat with John.
* RetroactiveRecognition: Is that [[Series/GossipGirl Dan Humphrey]]/[[Series/You2018 Joe Goldberg]], playing the smart largely ignored high schooler trying to get the blond's attention?
* {{Squick}}: The final scene during the credits with all of the old men wearing thongs.