The story takes place in the 1930s, when young Bob (Jesse Eisenberg) went to Hollywood to join his uncle Phil (Steve Carell), who was making a name for himself there. Under Phil's introduction, Bob met a cute girl named Vannie (Kristen Stewart). The lively and talkative Vannie soon made Bob fall in love, but unfortunately, Vannie told Bob that she already had a boyfriend. One day, the heartbroken Vannie found Bob, and it turned out that her boyfriend was a married man, who decided to break up with him because he could not make up his mind to divorce his wife. Bob accompanied the lovelorn Vannie gently and patiently, and as time went on, the two slowly came together. What Bob did not expect was that Vannie's ex-boyfriend was Phil. When Phil made up his mind to marry Vannie, Vannie left Bob without hesitation. Afterwards, the frustrated Bob returned to his hometown and worked as a waiter in the club run by his brother Ben (Corey Stoll), where he met Veronica (Blake Lively). They got married and had children, and everything seemed so beautiful until one day, Vannie and Phil appeared by Bob's side again.