- Fridge Horror: Colson was very clearly falling in love with Josie. But the thing is, he had no idea about her true age. No one did. So it could be argued that he fell in love with a high school girl.
- Remember, though, that Josie was playing an 18 year-old student at the time and he doesn't seem that much older.
- More straddling the line between this and Fridge Logic, but - Rob is a 23-year-old pretending to be a high-school student, who plays baseball. Most, if not all, governing bodies would force South Glen South to forfeit the games in which he played, as players over 18 are a big no-no a high school sports.
- Hilarious in Hindsight: Seeing James Franco as one of the popular jerks and Leelee Sobieski as a bully-target becomes almost karmic when you see the ending to The Wicker Man (2006).
- Hollywood Homely:
- Leelee Sobieski as the nerdy girl, especially when she strips down to that spandex blue cat suit at the prom.
- Also Josie Geller — she's supposed to be a bookish, nerdy girl as well... but she's Drew frickin' Barrymore! That said, they do manage to make Drew look pretty bad in her prom flashback. More than the majority of these examples, anyway.
- Retroactive Recognition: Hey, who's that guy getting hit in the face with a purse? That wretched James Franco, of course!
- Squick: It's rather creepy how Rob pretended he dated Josie. And don't his friends ask how she was in bed, to which he replies, "She's amazing." And then don't they lean in and want details WHICH HE THEN HAS TO DESCRIBE??? Yeah, it's a charade, but seriously?
- Tear Jerker: Josie's flashback to the night of her prom. Her younger self giddily rushes to her front porch to meet her date... only for him and his real date to cruelly pelt her with eggs and drive off, leaving young Josie sobbing. Also a bit of realistic Nightmare Fuel to those who were picked on in high school.
- Values Dissonance: The "dunce sombrero" that Josie sports for being late to class might double as cultural appropriation and an archaic form of punishment during the time of movie setting.
- What an Idiot!: Why exactly did Rickford assign a copy editor to do a huge story anyway? Does he randomly assign stories to random people? If he could fire his own cousin for a lackluster story, what exactly did he expect from a copywriter who hasn't cut her teeth on any stories yet?
- He's the owner of the paper, not the daily manager. It seems he decided based on the fact that Josie was really the only one who was young enough to possibly pretend to be a high school student.
YMMV / Never Been Kissed