Cal Weaver is a middle-aged man who is told by his wife Emily that she has cheated on him with a co-worker, David Lindhagen, and wants a divorce. After moving into his own apartment, son Robbie and daughter Molly staying at the house with Emily, Cal goes to a bar night after night, talking loudly about his divorce, until he attracts the attention of a young man named Jacob Palmer, a womanizer who beds different women each night, although a young woman named Hannah has recently rejected his advances. Jacob takes pity on Cal and offers to teach him how to pick up women. Using Jacob's teachings, Cal seduces a woman named Kate at the bar. After the encounter, Cal manages to successfully seduce other women at the bar. He sees Emily again at their 13-year-old son Robbie's parent-teacher conference. The interaction goes well until they discover that Robbie's teacher is Kate, who reveals to Emily that she and Cal have had sex together. Cal then confesses to having sex with nine women since their separation. Emily leaves in disgust and begins actively dating David. Meanwhile, Hannah, a recent law school graduate, is expecting her boyfriend Richard to propose marriage while they celebrate her passing the bar exam, but he does not, instead, offering her a position at his law firm. Offended and hurt, Hannah returns to the bar where she originally rejected Jacob's advances and kisses Jacob passionately.
At the same time, Robbie makes numerous grand gestures to try to win the heart of his 17-year-old babysitter, Jessica Riley, who actually has a crush on Cal. On the advice of her classmate Madison, she takes nude photos with raunchy expressions of herself to send to Cal and tucks them away in an envelope inside her dresser drawer. Later, Emily calls Cal under the guise of needing help with the house's pilot light, but Cal sees through the ruse since he is secretly gardening at the old house in the night and sees that Emily did not really need any help. Realizing that she called just because she too was missing him, Cal decides to try and win her back. Meanwhile, Jacob returns Cal's calls and asks for advice about being in a real relationship and meeting his girlfriend's parents. Jessica's mother, Claire, friends with Emily, who dislikes Cal, discovers Jessica's naked photos in the dresser drawer and shows them to Jessica's father, Bernie. Bernie was Cal's best friend before Claire made him end their friendship in the aftermath of the breakup. Bernie rushes to the Weaver residence 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 at the house, 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. At that moment, Bernie shows up and attacks Cal. Jessica arrives and tells her father that Cal knew nothing of the pictures. Then David arrives on the scene to return Emily's sweater from a previous date. Jacob asks David if his name is Lindhagen and when David replies "yes," Jacob 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 and receives a visit from Jacob, who confesses that he is in love with Hannah. Cal replies that he is happy that Jacob is a changed man but does not approve of Jacob and Hannah's relationship, having seen Jacob's 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, Robbie is the salutatorian and gives a pessimistic speech about how he no longer believes in true love and soulmates. Cal stops him and instead begins to recount his courtship with Emily to the audience, saying that, while he does not know if things will work out, he will never give up on Emily. 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 the nude photos of herself that were originally intended for Cal to "get him through high school." Cal and Emily have a laugh talking about the events that have transpired the past year, hinting that they might get back together.
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