Cal Weaver is a middle-aged family man whose wife Emily asks for a divorce after she reveals an affair she had with co-worker David Lindhagen. The news stuns Cal, who jumps out of their moving car when Emily tries to talk about the affair. The divorce also ends his friendship with best friend Bernie Riley, whose wife sides with Emily over Cal. After moving into his own apartment, Cal begins frequenting an upscale bar, where he talks loudly about his wife cheating and divorce. He meets Jacob Palmer, a young man and womanizer who frequently beds different women but was recently rejected by a law school graduate, Hannah. Jacob takes pity on Cal and offers to teach him how to pick up women. After a few awkward attempts to talk to women, Cal seduces Kate at the bar. This experience gives him the confidence to seduce 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 they meet Robbie's teacher, who turns out to be Kate, and who spitefully reveals her and Cal's tryst because he never called her afterwards. In the ensuing argument, Cal inadvertently confesses to having sex with nine women since their separation, so Emily leaves in disgust that Cal did this as payback for her cheating while also openly dating David. Cal and Emily's son Robbie makes numerous grand gestures to win the heart of his babysitter Jessica, who is Bernie's daughter. She eventually dissuades him after revealing she likes someone older, without revealing it is Cal. On the advice of a promiscuous 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. Meanwhile, Hannah is offended by her boyfriend when he offers her a position at his firm instead of proposing as expected. She returns to the bar, finds Jacob, and throws herself at him. As Jacob ends up walking her through his process of seducing women, they end up developing genuine chemistry and start dating. 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, which make her and Bernie believe that Cal and Jessica are in an illicit relationship. He furiously drives to Cal's, with Jessica following to stop him. 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 as teens. Cal is appalled that Jacob is dating his daughter, and forbids her from seeing him. Emily supports their relationship. Bernie and Jessica then arrive, revealing to everyone Jessica's and Robbie's respective feelings. David also arrives on the scene to return Emily's sweater from a previous date. Cal, Jacob, David, and Bernie then get into a scuffle which is soon broken up by the police. With Cal now worse off with his family than ever before, Jacob warms up to them as his and Hannah's romance blossoms. Jacob finds Cal at the bar and confesses that he is in love with Hannah and has therefore re-evaluated his life. Cal is happy that he is a changed man but does not approve of their relationship, having seen his former lifestyle. Jacob does not harbor any ill feelings and praises Cal for being a great father. At Robbie's eighth grade graduation,
salutatorian Robbie gives a pessimistic speech about how he no longer believes in true love. 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 for emotional support. Robbie then smiles optimistically as he watches Cal and Emily talking together. == Cast ==