One evening, Jacob takes Hannah to the same club where Cal is picking up women. Hannah sees Cal with a random woman. She recognizes Cal—he’s the father of a student she tutors (a small world coincidence). Jacob is furious at Cal for lying about his real life. They argue.
Cal’s 13-year-old son, Robbie (Jonah Bobo), is hopelessly in love with his 17-year-old babysitter, Jessica (Analeigh Tipton). Jessica ignores Robbie’s advances but secretly has a massive crush on Cal, even taking nude photos of herself for him (which she never sends, but her mother finds them, causing a scene).
Months later, at Robbie’s school talent show (where Robbie performs a rap about his love for Jessica), Cal gives a speech. He doesn’t win Emily back with grand gestures. Instead, he shows up, sits next to her, and says he’ll wait. He accepts that love isn’t perfect or logical. Emily takes his hand.
Cal transforms physically and mentally. He becomes a hit with women at the club, going home with a different woman almost every night. He feels empowered, but it’s hollow. Meanwhile, Jacob’s own commitment-phobic lifestyle is challenged when he meets a bright, ambitious law school graduate named Hannah (Emma Stone). Jacob and Hannah’s Romance The bet: Jacob, who never does repeats, sleeps with Hannah on their first date. Impressed by her wit and refusal to be charmed (she calls him out on his pickup lines), he finds himself drawn back to her. Hannah, despite knowing his reputation, agrees to see him again.