Cal (Steve Carell) and Emily Weaver (Julianne Moore) are awkwardly having dinner at a restaurant. Cal complains about having filled up on two much bread and notices that Emily seems a bit off tonight. When he mentions not knowing what he wants (off the desert menu), Emily blurts out that she wants a divorce, causing everyone in the room to stare at them.
Back at the Weaver household, babysitter Jessica is looking after the youngest Weaver children, thirteen year old Robbie and 8 year old Molly while Cal and Emily are at dinner. Molly runs too fast and knocks over a framed photo of her mom and dad which shatters. Jessica picks up the photo and covers Emily’s face, starring lovingly at Cal. She goes to check on Robbie in his room, only to find him jerking off.
On the drive home, Cal doesn’t say anything. He gazes out the mirror on the verge of tears. Emily tells him that she slept with someone and asks how he has nothing to say after 25 years of marriage. She then starts talking about the man she slept with, an accountant named David Lindhagen who Cal met at the last Christmas party. Cal throws himself out of the moving vehicle so he doesn’t have to listen to any more of his wife talking about it. She stops the car and goes to see if he’s alright but he tells her that he’ll leave tonight and will sign anything she wants him to sign if she stops talking about it. On the drive home they both realize they’ll have to tell everyone about their divorce and how much they’ll disappoint Nana.
Robbie approaches Jessica in the living room and apologizes for what she saw. He then confesses his love to her and talks about how he only thinks about her when he does the deed, simultaneously shocking and creeping her out. He tells her that age shouldn’t be an issue since she is only four years older than him, but she shoots him down. His parents arrive home and Jessica asks what happened when she sees Cal’s beat up suit. Cal blurts out that he jumped out of a moving car and is getting a divorce, which Robbie is shocked to hear. Cal apologizes to Robbie for having to hear about it like this but Robbie is still more focused on the fact his dad jumped out of a moving vehicle.
At a bar in LA, Hannah (Emma Stone) is out with her best friend, Liz, talking about Hannah’s prospects and future. Across the bar, Jacob Palmer (Ryan Gosling) is admiring her and decides to talk to her. He casually begins a conversation and she is confused that he would open with something that seems like a pick up line. Jacob explains that it’s not a line by pointing out that in a room full of beautiful women, she’s the only one who he couldn’t take his eyes off for the last two hours. He asks if she wants to get out of there but she rejects him, instead leaving him surprised and fairly amused.
Cal takes Jessica to her parents’ house and Jessica offers her sympathies, explaining that Cal is one of the nicest dads that she babysits for. She tells him that Emily is a crazy person for wanting to divorce him and Cal thanks her for the kind words. As she awkwardly tries to confess her feelings, he drops her off and asks that she not tell her parents about the divorce. Jessica winds up standing on the sidewalk awkwardly watching Cal drive away.
Cal goes to the same bar two nights in a row and meekly gets wasted off of cranberry vodka. He talks to random women about how his wife cheated on him with David Lindhagen. His best friend Bernie, Jessica’s father, pays him a visit and tells him that he and his wife don’t want to pick sides, but they chose Emily. He presents Cal with a gift of cologne and leaves a rejected Cal to rant to the bar patrons some more. Jacob, who is sitting at a table with another woman, beckons Cal to join him.
Jacob looks at Cal and tells him that all he has been doing for the last two nights is come to the bar and depress everyone with his sad story. He calls Cal pathetic and tells him that the reason he lost Emily is because he lost sight of who he is as a man. He offers to help make Cal a man again and make Emily rue the day she left him. Cal is surprised and a bit unsure of Jacob and asks why Jacob is so willing to help him. Jacob tells Cal that Cal reminds him of someone and tells Cal to meet him at the Century City Mall on Thursday to begin the process.
At work, Emily is in the copy room when David Lindhagen (Kevin Bacon) comes to talk. He playfully accuses her of avoiding him by pointing out that the other day she saw him the hall and literally turned around to run away from him. He explains that the never intentionally tried to seduce her and he didn’t plan on falling for a married woman, but that he doesn’t regret it. Emily is in an awkward situation and tries to hide the fact that she’s photocopying pages from Divorce for Dummies, and relieved when David walks away.
Robbie and Molly visit Cal at his new apartment. Robbie mentions that he is in love with someone and Cal brushes over it despite being sympathetic since it is Thursday and he has to meet Jacob at the mall. Jessica arrives to watch the kids and Cal meets Jacob. Jacob takes him on a shopping spree, encouraging him to rediscover his sense of style. After finding the right clothes, Jacob asks a young attendant if she would sleep with Cal. Cal is surprised when she says yes and begins laughing. The attendant changes her mind and Jacob points out that the more Cal talks the less inclined women want to sleep with him. The next step will be to help Cal with learning how to talk to women.
Over the next couple weeks, Cal follows Jacob around and observes Jacob’s approach to women. One night, Jacob tells him that it’s time to put all the Karate Kid skills to work. Cal is confused and Jacob explains: Mr. Miyagi’s “Wax on Wax” approach was being applied. Jacob asks Cal to explain how he sealed the deal every single time. Cal points out that Jacob doesn’t talk about himself, he always makes the girl have to work for his attention while striving to be more interesting to him and then when he wants to go home he says “let’s get out of here”, not as a question but as a statement giving the ladies no chance to make a decision. Cal is shocked when he realizes that he knows all the steps. Jacob points him out to a woman in a blue dress that Cal will take home tonight.
Cal and Jacob approach the woman (Marisa Tomei) and Cal introduces himself, but brushes off Jacob so that he can tackle this one on his own. Jacob observes from the bar as Cal follows his steps to disastrous effects. Cal tells the woman that he’s going to buy her a drink: she’s five years sober. He asks her what she does without telling her what he does. When she tells him she is a teacher he calls her boring. Striking out, she prepares to leave and he confesses that his wife cheated and left him and that he came to talk to her because she reminded him of Emily who was “the perfect combination of sexy and cute.” The woman introduces herself as Kate and they go back to Cal’s place and have sex. The next morning, Kate tells her to call him but he’s too scared of her to even think about it. He continues following Jacob’s routine and takes home more and more women.
Robbie texts Jessica while in English class to see if she will reconsider but she responds that he makes her uncomfortable. His teacher asks him to contribute to the discussion on the Scarlett letter. Robbie stands up and gives a speech about how the main characters were all Assholes for falling in love, which was why they all had to wear the letter A on their chests. His teacher sends him to the office and Emily comes and picks him up.
Emily brings Robbie to her workplace since she cannot find a mid-day sitter for him. Robbie notices a photo of Cal and Emily and Emily realizes that she should put it away. She asks about Cal and Robbie explains that he’s been going out a lot, which disappoints her. Then Robbie explains that he knows they both miss each other since Cal is always sad and he heard Emily crying in her room the night before. She is embarrassed but they laugh about it when David comes in. Emily leaves the room to make some photocopies and David tries to make friends with Robbie. Robbie cuts him down by calling him a home wrecker and telling David that Cal will get Emily back because Cal “is better than you in every way.” Emily returns to get her things and go home, leaving David alone in his office to reflect on the consequences of his actions.
At school, Jessica goes to the resident bad girl, Claire, for advice on how to get older men to see her as a serious romantic prospect. Claire tells Jessica to take naked photos of herself and mail them to him in order to guarantee that he stops seeing her as a child. Jessica leaves the school for lunch and sees a giant scaffold covered by red drapes. The drapes drop to reveal Robbie, who confesses his feelings in a cliché romantic gesture. He embarrasses her and she yells at him, telling him that she is seeing an older man. He is angry but accepts it bitterly.
Parent teacher conferences arrive. Emily and Cal meet to learn more about Robbie’s performance in school and awkwardly sit next to each other while waiting for the teacher to see them. They confess that they miss each other and talk about their Nana, who is worried about both of them. On the tip of reconciliation, the door opens to reveal that Robbie’s English teacher is none other than Kate. She talks about Robbie’s Asshole rant and explains that a real asshole is someone who says that they’ll call and never does. Emily realizes that they aren’t talking about Robbie and asks Cal to explain the situation. Cal says Kate is an alcoholic and runs after Emily when she leaves.
In the parking lot, he confesses that he’s been sleeping with a lot more women but that it wasn’t about showing Emily what she was missing but because he wanted to get over her. He tells her he can’t because she’s his soul mate. Kate arrives and tells him to call Emily “the perfect combination of sexy and cute.” Emily is horrified that Cal used those words to describe Kate and asks him “Who are you?” before storming away. She leaves Cal standing in the rain.
Hannah passes her bar exam and goes out to celebrate with Liz and her attorney boyfriend, Richard (Josh Groban). Richard told her that after she passes the bar, he’d take her out and make the night memorable. Assuming that he was going to propose, she is disappointed when all he does is offer her a job at his firm. She confesses that she thought he was going to propose but he surprises her by saying he never thought they were at that point or even that serious. He tells her he needs time to see where they’re going in the long term and she responds by saying she will consider his job offer. She storms out the rain and goes back to the bar where she met Jacob due to Liz’s encouragement. She finds him and kisses him passionately, demanding that he bring her home. He is thrilled to oblige.
At Jacob’s house, he carefully prepares a drink for Hannah and himself and she downs both glasses while muttering “not my favorite.” She asks how “this” works and he tells her that he can tell she’s nervous and explains that he acts out the end scene of Dirty Dancing with women and it makes them want to sleep with her. They re-enact the scene and they go to the bedroom…where she realizes that his pillow is from the home shopping network. They talk for hours and look at all the things Jacob bought from the home shopping network. She asks about his mom and dad and he explains that his mother is beautiful, vain and a handful. His dad died years earlier after making a small fortune but that he was a bit of a weak man who couldn’t handle his wife. He falls asleep next to Hannah and she gently kisses him goodnight.
Cal continues to go to the bar but doesn’t see Jacob at all. Weeks pass and he leaves one final message of concern. He calls Emily but she’s on a date with David. They have a genuine chemistry but Emily is still embarrassed about him. Jessica sees them together and David leaves awkwardly. Emily tries to pay Jessica for watching the kids but Jessica instead ridicules her for leaving Cal, who is a fantastic person and a great father. She storms off, leaving Emily confused. Jessica goes home and takes several naked pictures of herself and slips the best ones into a letter for Cal which she hides in her clothes drawer.
Robbie tells Cal that if he has to go big or go home if he’s going to win Emily back. Cal sneaks home in the middle of the night and begins cleaning up the garden after having a nightmare of David doing the yard work around the house and replacing him. He gets a call from Emily who he can see in the living room. She tells him that the pilot light turned off and he is touched because he can see that she just wants to hear his voice. He earnestly describes the generator scene from Jurassic Park (minus the dinosaurs) and tells her to call him any time. Realizing that she still loves him, he makes preparations to surprise her.
Cal goes to Home Depot with his kids to get all the necessary materials to build Emily a miniature golf course to capture the nostalgia of their first date from when they were 17. Cal brushes off Bernie in the store and gets a call from Jacob. Jacob tells Cal that he met an amazing girl who is a game changer, which causes Cal to laugh. Jacob tells him that he is meeting Hannah’s mother for the first time today and Cal tells him to not be himself. Jacob laughs and asks if he’d like to get a beer next week to which Cal agrees, telling Jacob that he will be a hit with Hannah’s parents. At Jessica’s house, her mother discovers the nude photos and shows them to Bernie. Bernie sees who the envelope is addressed to and runs to his car, going to go beat Cal senseless. Jessica realizes what happened and chases after him in her own car to explain that Cal doesn’t even know that Jessica is in love with him.
Emily arrives home and sees Molly and Robbie waiting for her. They blindfold her and lead her backyard. Emily is tired of waiting and takes off her blindfold and calls out to Nana, who has arrived with her boyfriend. Nana turns out to be Hannah, Cal and Emily’s oldest daughter. Cal is surprised and then outraged to see that Jacob is with Hannah. Before he can process anything, David Lindhagen arrives and introduces himself, awkwardly. Jacob sees him and punches him in the face for Cal. Cal then attacks Jacob for dating Hannah, only to be tackled by Bernie. Jessica arrives and screams that Cal didn’t know anything about her feelings for him, which breaks Robbie’s heart.
The cops arrive and bust up the fight, telling them to “fight in doors. Keep it in the family.” Bernie and Jessica leave. Cal yells at Hannah and demands that she stop seeing Jacob because he knows what Jacob is really like. He tells her that if she won’t leave him she isn’t welcome in his house. Emily angrily tells him that it’s not his home anymore and he snaps that she made damn sure of that. He tells David that Emily is all his. He looks at Robbie and Robbie tells him to go home, angry that he was main competition for his soul mate was (unwittingly) his father.
Weeks pass. Cal uses his vacation days to drink at the bar during the day. Jacob visits him and asks him if he’s ever going to go around and see his kids instead of drinking. Cal brushes him off brusquely and tells him that he’s seen too much: he will never give Jacob his approval. Jacob expresses his feelings for Hannah in earnest and tells him that he used to think that people like Cal and his father were pathetic but that he was missing out on something amazing. He calls Cal a good father and tells him to go to Robbie’s 8th grade graduation.
Cal arrives at the graduation but doesn’t sit with his family. He sees Jacob with Hannah and how tender he is with her from a far. Robbie, as salutatorian, gives a speech about how much he wanted to grow up and then expresses his contempt for love, which causes Cal to stand up and stop him. He gives his own speech about how he became a dad at age 17 and that he met his soul mate when he was 15. He explains that love is the best thing you can have in life and encourages his son to keep that in his heart, even if it’s unrequited. Robbie happily proclaims that he still loves Jessica even though she walked in on him masturbating (which causes Cal to turn off the microphone).
After the ceremony, Cal and Jacob talk and he accepts that Hannah can be with the person she loves. He slaps Jacob in the face several times, which Hannah finds amusing. The couple goes off to fool around with Molly and keep her entertained. Jessica approaches Robbie and he tells her that in a few years he will look like his dad. He’ll come after her again then. She smiles and slips him an envelope with some pictures and gives him a kiss while he looks at them stuttering. Emily and Cal look at their children and point out that it’s been a hell of a year. They laugh and joke around, leaving their kids to look at them together, the possibility of reconciliation stronger than ever.
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