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  • Designated Hero: 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 absolutely no embarrassment about, and how he truly seems to believe he's entitled to a relationship with her because he's "nice", and many people end up seeing him as a Creepy Child Stalker with a Crush. The fact that he never learns a lesson about respecting people's wishes and not making them feel uncomfortable, and instead gets rewarded for his behavior with nude photographs of his crush makes it even harder to root for him. Slightly mitigated by him apologising to her for making her feel uncomfortable and saying that he's not going to pursue her for now, but still.
  • Fridge Logic: 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.
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    • Also, do none of these women that Jacob sleeps with then never calls again ever return to the bar?
      • 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.
      • A couple were actually blocking Cal clearly from Liz' view.
      • As for Jacob's conquests returning to the bar they probably do but he never seems to suggest he's going for anything but a one night stand from the beginning so they have little reason to go back to talk to him.
  • Harsher in Hindsight: 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...
  • Heartwarming in Hindsight: Jacob's treatment of Cal makes more sense when it's revealed that his father, like Cal, was a kind, if weak-willed, man who also didn't fight to keep his wife interested in him.
  • Hilarious in Hindsight:
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    • 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' 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.
    • Marisa Tomei's character grows to hate Steve Carell's here, whereas in The Big Short they play husband and wife; likewise, Carell and Emma Stone play father and daughter here, but are rivals in Battle of the Sexes.
    • Robbie saying that The Scarlet Letter's "A is for asshole" seems to be a Take That! to those that insulted his sister Hannah as played by Emma Stone who starred in Easy A. Easy A is considered an updated version of said book.
    • Emily finding out Kate slept with her husband when, in 2019, Marisa Tomei and Julianne Moore discovered they were cousins.
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    • At one point, Cal observes that the word "cuckold" is not used very often anymore. In the years since the film's release (particularly since 2016), that word has become an extremely popular slur among conservatives and alt-right (especially its abbreviated form, "cuck").
    • Jacob telling Cal that the "battle of the sexes is over, and we won." Steve Carell (Cal) and Emma Stone (Hannah) would later play rivals in Battle of the Sexes, and she wins.
  • Jerkass Woobie: 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 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.
  • Memetic Mutation: Robbie's Scarlet Letter "A is for asshole" speech in class.
  • Narm: Hannah's misunderstanding about the proposal is made rather less believable by how Richard repeatedly says he'll be making his announcement if she passes the bar. Apparently she's perfectly fine with his making their engagement contingent on her graduation.
  • Squick: Jessica's parents find her nude photos and her father looks at every...single...one.
  • Unfortunate Implications: Multiple critics have called out the film for portraying 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.
  • Unintentionally Unsympathetic: Jessica. While she didn't deserve all the things Robbie did to her (see Designated Hero above) her actions end up proving to be just as bad. She's a hypocrite for rejecting Robbie by saying that he was too young for her (he's 13 while she is 17 so it's a 4 year difference) yet she tried to seduce his father Cal despite the HUGE age gap (she's 17 while he's 44), the fact that he's clearly not interested and the fact that he just went through a divorce. Ignoring those factors, she later takes nude photos of herself and saved them so that she could send them to Cal later (which would've been a charge of child pornography on Cal and would've effectively ruined his life as well as Robbie's had her parents not found them first). The fact that said photos lead to her father attacking Cal after he falsely assumed the worst and that she later gives them to Robbie (a minor) at the end doesn't help.
  • Unlimited Wardrobe: Jacob takes Cal shopping to rebuild his wardrobe with, "like sixteen items," and Cal spends the rest of the movie wearing a variety of expensive suits, clothes, and shoes. Cal also seems to have an Improbable Food Budget as he routinely racks up a very high bar tab.

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