* DesignatedHero: Robbie is presented by the film as a plucky, charming kid who never gives up on his love of his babysitter, even when the odds are stacked against him. Unfortunately, his love quest involves constantly following the girl around badgering her to date him, staging elaborate displays of affection that make her a laughing stock, acting like she's cheating on him when he finds out she likes someone else, and even turning his valedictorian speech into a passive agressive rant about not believing in love anymore because a crush turned him down. Add in the fact that this comes to light because she caught him masterbating to her, which he has [[TroublingUnchildlikeBehavior absolutely no embarrassment about]], and how he truly seems to believe he's [[EntitledToHaveYou entitled to a relationship]] with her because he's "nice", and many people end up seeing him as a CreepyChild StalkerWithACrush. The fact that he never learns a lesson about respecting people's wishes and not making them feel uncomfortable, and instead [[spoiler: gets rewarded for his behaviour with nude photographs of his crush]] makes it even harder to root for him.
* FridgeLogic: [[spoiler: Liz is presumably a very close friend of Hannah's. Has she never met Cal or seen pictures of him, enough to recognize that he's the guy Jacob is with at the bar? Not only that, but it appears that Hannah goes to the bar fairly often, yet never once ran into her father there.]]
** Also, [[spoiler: do none of these women that Jacob sleeps with then never calls again ever return to the bar?]]
*** [[spoiler: Hannah pretty much puts her social life on hold in order to study for the bar exam. She stops going out the same time Cal starts frequenting the bar. And Liz might only go to that bar with Hannah, rather than by herself.]]
*** [[spoiler: A couple were actually blocking Cal clearly from Liz' view.]]
* HarsherInHindsight: Robbie cites Ashton Kutcher and Demi Moore as an example of a younger man/older woman relationship that's gone strong. Cut to a year after the film's release...
* HateDumb: In-universe. Hannah's friend's reason for disliking her fiance is solely that he's nerdy and boring. Jacob is hot and fashionable so the fact that he's a womanizer is a non-issue with her.
* HilariousInHindsight: Hannah insists that her love life is not PG-13. Guess what the movie's rating is?
** Jacob wants to help Cal, because 'he seems kinda familiar'[[spoiler: which happens right after he met Hannah. Cal reminds him of Hannah because they're father and daughter.]]
* MemeticMutation: Robbie's ''Scarlet Letter'' "A is for asshole" speech in class.