Cal Weaver (Steve Carell) gets the surprise of his life when he learns that his wife Emily (Julianne Moore) cheated on him with a coworker, David Lindhagen (Kevin Bacon), and wants a divorce. After moving into his own apartment, Cal begins frequenting a bar night after night, talking loudly about his divorce, until he attracts the attention of a young man named Jacob Palmer (Ryan Gosling). Jacob is a womanizer who successfully beds women each night, although a young woman named Hannah (Emma Stone) firmly rejects his advances. It is clear Hannah catches Jacob's eye. However after she leaves, Jacob takes pity on Cal, Jacob agrees to teach him how to pick up women. As they spend their evenings at the bar together, a friendship begins to blossom.
On Cal's first attempt to seduce a woman he meets Kate (Marisa Tomei). She initially rejects his awkward advances, but eventually they sleep together. Cal manages to successfully seduce multiple women; nevertheless he can't seem to forget his wife. He sees his wife again at his son Robbie's (Jonah Bobo) parent-teacher conference. The meeting goes well until they discover Robbie's teacher is Kate, who reveals to Emily that Cal had seduced her. Emily leaves in disgust and begins actively dating David.
On Cal's first attempt to seduce a woman he meets Kate (Marisa Tomei). She initially rejects his awkward advances, but eventually they sleep together. Cal manages to successfully seduce multiple women; nevertheless he can't seem to forget his wife. He sees his wife again at his son Robbie's (Jonah Bobo) parent-teacher conference. The meeting goes well until they discover Robbie's teacher is Kate, who reveals to Emily that Cal had seduced her. Emily leaves in disgust and begins actively dating David.
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