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Cal Weaver (Steve Carell) is living the dream - he's got a good job, nice house, and great kids. Cal gets the surprise of his life when he learns his wife Emily (Julianne Moore) has been cheating on him with a coworker, David Lindhagen (Kevin Bacon), and wants a divorce. After moving into his own apartment, Cal begins grieving at a bar night after night talking to himself about his situation where he meets a young man named Jacob Palmer (Ryan Gosling). Jacob is a womanizer who successfully beds women each night, although he does take a particular interest in a young woman named Hannah (Emma Stone), the only woman to resist his advances. Not wanting to watch Cal keep draining his sorrows night after night, Jacob agrees to teach him his trade so that he can have the confidence to earn Emily back. Because Emily is the only woman Cal has even been with, Cal doesn't have much experience, so Jacob gives Cal a makeover and has him watch his tricks at the bar.
This film features examples of:
- Billing Displacement: Analeigh Tipton has a bigger part than Marisa Tomei, guess which one is on the poster...
- Caught with Your Pants Down: Robbie does it while thinking of Jessica, his babysitter that he loves.
- Chekhov's Gunman: Nana. That is all.
- Dawson Casting: 22-year old Analeigh Tipton as 17/18 year old Jessica. Not as bad as other examples, but still there.
- Don't Explain the Joke: After admitting that she has a crush on an older man (Cal) to one of her friends, Jessica is ensured by said friend that her "lips are ARF ARF", accompanied by the friend clapping her hands. Not following, Jessica asks for an explanation as to what she means. Basically, "Our lips are seals." As in, "our lips are sealed".
- Gray Rain of Depression: Lampshaded by Cal after he blows it with Emily at the parent/teacher conference and it begins to rain...
"Oh, that is such a cliché."
- Ladykiller in Love: Jacob for Hannah.
- Hair Color Spoiler: It's a bit obvious that Hannah and Emily both have red hair. It's no wonder they end up being mother and daughter in a film with such a tangled web of associations.
- Heroes Want Redheads: Emily and Hannah.
- Madness Mantra: Cal's incessant babbling about the man with whom his wife committed adultery, and the whole "cuckold" thing, come off a bit like this.
- Lawyer-Friendly Cameo: Jacob and his methodical approach to picking up seems to be a clear allusion to the professional pickup artists subscribing to the "Mystery Method" and its successors, as described in Neil Strauss' book The Game.
- Love Dodecahedron: Robbie has a thing for his babysitter Jessica who has a crush on Robbie's father Cal who is going through a really rocky relationship with Emily, who had a one-night stand with David but is also the mother of Hannah, who's the girlfriend of Jacob, who teaches Cal how to "regain his manlihood," which allows him to pick up multiple women, one of whom turns out to be his son Robbie's teacher, etc.
- Papa Wolf: Cal's reaction upon finding out about Jacob and Hannah, and Jessica's father's reaction when he thinks Cal is involved with his daughter.
- Precision F-Strike:
"Fuck! It's like you're Photoshopped!"
- Realistic Diction Is Unrealistic: Averted; characters trip over their own tongues, repeat words, have awkward pauses in the middle of or between sentences, interrupt each other or don't finish their thoughts. This seems to be common in Steve Carrell films.
- Romantic False Lead: David
- Sensei for Scoundrels: Jacob is this for Cal, although he never teaches Cal to mistreat women. Also, Jacob is much younger than Cal but much more experienced in this regard.
- The Reveal:
- Marisa Tomei's character is Robbie's teacher.
- Hannah is Cal and Emily's daughter.
- Stalking Is Love: Robbie's crush on his babysitter is at heart really disturbing, but is presented in a romantic positive light by the film.
- The Unfair Sex: Emily cheats on Cal and tells him she wants a divorce (although she's not specifically leaving him for the other man) and their friends take her side--but all are incensed at the rumors of Cal's womanizing.
- Unexplained Accent: As Jacob, Ryan Gosling puts on something of a NooYawk/Joisey accent, despite the film most likely taking place in LA.
- He also speaks Yiddish as a Second Language, so presumably he's a transplanted New Yorker
- Take That: "I tried watching the Twilight movie by myself. I don't know what I was thinking. It was so bad!"
- Writers Cannot Do Math: How old is Hannah supposed to be? She's old enough to be taking the bar and her parents had her at the age of 17, but she's played by 22-year-old Emma Stone. This leads to some confusion for the audience. Is this supposed to be an inverted case of Dawson Casting?
- Cal states that her birth was what forced them to marry so young, and they've been married for 25 years, so presumably she's 25/26, tops.
- Same with Emily being 44, for the same reason.
- Emily is 44, and they've been married almost 25 years, so they got married when they were 19 or 20, but they got pregnant when they were 17, which is why they got married. Shotgun weddings aren't really supposed to happen when the kid is two. So unless Emily's three years older than Cal, which would make it kinda weird that they first went out when he was 15, there's something fishy going on.
- Like father, like son.
- Shout-Out of sorts, given that Robbie is reading The Scarlet Letter in class and Emma Stone starred in Easy A.