* FridgeHorror: 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 [[{{Squick}} 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 FridgeLogic, 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.
* HilariousinHindsight: 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 TheWickerMan remake.
* HollywoodHomely:
** Creator/LeeleeSobieski 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 frikkin' Barrymore! That said, they do manage to make Drew look pretty bad in her prom flashback. More than the majority of these examples, anyway.
* RetroactiveRecognition: Hey, who's that guy getting hit in the face with a purse? That wretched JamesFranco, of course!
** And Creator/JessicaAlba is totally Disco Barbie!
** [[Film/TheHelp Octavia Spencer]] also has a minor role.
** Creator/JohnCReilly as the newspaper editor.
* {{Squick}}: I'm sorry, but is anyone else creeped out that 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???'' I get that it's a charade, but seriously?
* {{Tearjerker}}: 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.
* WhatAnIdiot: 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 copy writer 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.