Crazy, Stupid, Love

Cal Weaver is a middle-aged man whose wife Emily asks for a divorce after she reveals an affair she had with co-worker David Lindhagen. After moving into his own apartment, Cal begins frequenting an upscale bar, talking loudly about his divorce, until he attracts the attention of a young man named Jacob Palmer.

Jacob, a womanizer who beds different women each night, was recently rejected by a woman named Hannah. He takes pity on Cal and offers to teach him how to pick up women. After a few awkward attempts to talk to women, he seduces Kate at the bar. This experience gives Cal the confidence to approach other women, and he begins to emulate Jacob's example successfully.

Eventually, Cal and Emily reunite at their 13-year-old son Robbie's parent-teacher conference, where she is impressed by his newfound confidence and fitted clothes. Their reunion goes well until Robbie's teacher is revealed to be Kate, who shares with Emily that she and Cal have had sex. He inadvertently confesses to having sex with nine women since their separation and Emily leaves in disgust.

Meanwhile, Hannah, a recent law school graduate, is offended by her boyfriend as he offered her a position as a permanent lawyer at his firm instead of proposing to her. She returns to the bar where she originally rejected Jacob's advances, finds him, and asks if he still wants to take her home. Jacob takes her back to his luxurious home, but instead of becoming physically intimate, they spend the night talking and laughing until they both fall asleep.

Cal and Emily's son Robbie makes numerous grand gestures to win the heart of Jessica Riley, his 17-year-old babysitter, who has a crush on Cal. At the advice of a classmate, she takes nude photos of herself, intending to give them to him. Emily calls Cal under the guise of needing help with the pilot light, but he sees through the ruse. Realizing that she called just because she missed him, Cal decides to win her back.

Jacob returns Cal's calls, asking for advice about being in a real relationship and meeting his girlfriend's parents. Jessica's mother finds the naked photos and her father, Bernie, rushes to the Weavers' to confront him about the photos, with Jessica in pursuit. Cal and his kids create a makeshift mini golf set in their backyard to remind Emily of their first date.

During the gathering, Jacob and Hannah show up, and Hannah is revealed to be Cal and Emily's first daughter born to them right out of high school. Cal is appalled that Jacob is dating his daughter, and forbids her from seeing him. Bernie shows up and attacks Cal. Jessica arrives and tells her father that Cal knew nothing of the photos. David arrives on the scene to return Emily's sweater from a previous date. When Jacob identifies him, he punches him in the face for the pain he caused Cal. Cal, Jacob, David, and Bernie then get into a scuffle which is soon broken up by the police.

Cal starts spending time at the bar again, where Jacob finds him. He confesses that he is in love with Hannah and has begun to re-evaluate his life as a result. Cal is happy that Jacob is a changed man but does not approve of Jacob and Hannah's relationship, having seen his former lifestyle. Jacob resigns without harboring any ill feelings; rather, he expresses his respect for Cal and praises him for being a great father.

At Robbie's eighth grade graduation, as salutatorian Robbie gives a pessimistic speech about how he no longer believes in true love and soulmates. Cal stops him, and recounts his own courtship with Emily to the audience, saying that, while he does not know if things will work out, he will never give up on her. With renewed faith, Robbie reaffirms his love for Jessica, to the audience's applause.

After the ceremony, Cal gives Jacob and Hannah his blessing. Jessica gives Robbie an envelope containing her nude photos to "get him through high school." Cal and Emily have a laugh talking about the events that have transpired the past year, and watching them from afar, Robbie smiles optimistically.