* AssPull: TheReveal that [[spoiler: Hannah is Cal and Emily's daughter]] is this to quite a few people.
* 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 aggressive 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 masturbating 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 behavior with nude photographs of his crush]] makes it even harder to root for him.
** To be fair, he does apologise to her for making her feel uncomfortable and says that he's not going to pursue her anymore. At least, not until they're both a bit older.
* 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...
* HeartwarmingInHindsight: Jacob's treatment of Cal makes more sense when it's revealed that [[spoiler: his father, like Cal, was a kind, if weak-willed, man who also didn't fight to keep his wife interested in him.]]
* 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 reminds him of someone'[[spoiler: which happens three nights after he met Hannah. Cal reminds him of Hannah because they're father and daughter. Noticeably, they also both initially refuse Jacob when he offers to buy them a drink.]]
** The white-hot hatred that [[spoiler:Kate develops for Cal]] became funnier when their actors, Creator/SteveCarell and Creator/MarisaTomei, played a married couple in ''Film/TheBigShort''.
* JerkassWoobie: All the characters have moments where you want to hug them vs. moments where you want to slap them:
** Cal's trying to get over Emily. Jacob helps him get back in the game. When Cal finds out that [[spoiler: Jacob's dating his daughter (as in, seeing her for more than one night) his true opinion of Jacob surfaces, which makes him look like a hypocrite since he had no problem using Jacob's advice to treat women the way he didn't want his daughter treated.]]
** Jacob's a womanizer who believes that women need to be subdued. After spending some quality time with Hannah, he begins to warm up to the idea of having someone special in his life.
** Emily cheated on Cal for no justifiable reason. Only after Cal leaves does she realize that his absence has left a hole in her life and she genuinely seems to want to make things right.
** Jessica told Robbie that he was too young for her (4 years difference), then tried to seduce his father (27 years difference). Her plan to take nude pictures of herself and send them to Cal makes her look just as bad as Robbie to some.
** David slept with a married woman and basically tried to hijack Cal's entire life. Despite this, he does seem determined to do right by Emily's kids, though.
* MemeticMutation: Robbie's ''Scarlet Letter'' "A is for asshole" speech in class.
* UnfortunateImplications: [[http://moviemom.maxlazebnik.com/crazy-stupid-love/ Multiple]] [[http://moviemom.maxlazebnik.com/letter-to-steve-carell-re-crazy-stupid-loves-teen-nude-photos/ critics]] have called out the film for portraying [[spoiler:a teenage girl attempting to supply an adult with nude photos of herself (i.e., child pornography) before passing said photos on to a thirteen-year-old]] as an act of compassionate generosity.