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 provides examples of:
Abhorrent Admirer: Robbie to Jessica, mainly because he's 13 and he hounds her all over town explaining why she should go out with him after she catches him masturbating to her image. Subverted at the end when she takes pity on him and gives him her nudes.
Absurdly Youthful Mother: Played with. Emily is in her mid forties. She states that she got married very young implying this trope. It is a bit puzzling, as her children are fairly small (13 and below 10). We later learn that she is the mother of a 27 year old (Hannah) whom she had when she was a teenager.
Ambiguously Jewish: Jacob is fairly affluent because he comes from family money. His father is described as being "good with money". He affects a New York accent and sprinkles Yiddish as a Second Language into his speech, particularly his referring to his penis as his "schwantz".
Anti-Villain: David. The movie shows him to be a nice guy with seemingly genuine feelings for Emily, but doesn't excuse his role in breaking up Cal and Emily's marriage.
Blunt Yes: When David walks in in the middle of the fight in the back yard:
David: Is this a bad time?
Broken Aesop: Apparently practically stalking a girl, publicly humiliating her at her school, and repeatedly ignoring her pleas to stop contacting her because you are making her uncomfortable will get you, not a restraining order, but nudes.
Subverted. Jessica suffers Robbie because she knows he's 13 and doesn't know better. In fact she considers him sweet, but severely misguided.
Chekhov's Gunman: Nana. That is all. It's the Weaver's nickname for their eldest daughter; Hannah
Cool Big Sis: Its implied that Hannah is this to Robbie and Molly
Dawson Casting: 22-year old Analeigh Tipton as 17/18 year old Jessica. Not as bad as other examples, but still there.
Madison, the blonde girl with the "huge rack" whom Jessica solicits for advice was played by 23 year old Julianna Guill. The character was supposed to be 17 or 18 at most.
Inverted by 22 year old Emma Stone as 27 year old Hannah.
Divorce Is Temporary: Played with. Emily immediately asks for a divorce without trying to work anything out. They go back and forth with halfhearted efforts to work on things. In the end, Cal swears that he'll do everything he can to keep her. They seem like they are going to work it out, but even Cal says he has no idea if they will.
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".
Dumb Blonde: Its's OK to tell your secret to Madison because her lips are seals!
Genre Savvy: Cal pointing out the rain after the failed parent teacher conference (see below) and Hannah informing Jacob how things play out in the movies...
As Hannah says
"I know what happens in the PG-13 version of tonight!"
In-Series Nickname: Molly is called Cutie by her sister Hannah, who in turn is called Nana.
It Is Pronounced Tro PAY: Several characters pronounce David Lindhagen's last name as "Lind-hey-gen", even after he corrects them that it is pronounced "Lind-hah-gen".
Jerk with a Heart of Gold: Jacob genuinely comes to care about Cal and revere him as a friend. Even after Cal forbids Jacob to see his daughter. He sticks up for Cal when Bernie attacks him. He also punches David Lindhagen on sight for the effect Emily's affair with him had on Cal. When Hannah stops talking to Cal, it's Jacob who hands her a phone and says, "You should call your father."
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.
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.
Meaningful Background Event: During the scene where Robbie is at his mother's office, there are two picture frames. One is a photo of Emily and Cal, while the other is a picture of a baby girl who appears to be Molly... except it seems to look very old to be taken even in The Nineties and she obviously wasn't even born in that decade yet.
Oh Crap: Jessica has this reaction when her parents discover her nude pictures.
One Degree of Separation: All of the characters end up connected in various ways. The biggest is that Hannah is Cal's daughter but is is also significant that Cal's first one night stand is with Robbie's teacher.
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.
Hannah:(upon Jacob taking his shirt off) "FUCK! Seriously?! 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 Carell films.
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.
Cal consistently sneaks around his family's house and watches Emily. In one scene he happens to be in the yard while Emily calls him under false pretenses.
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.