Adventureland (2009)

Adventureland is a 2009 American retro comedy-drama film written and directed by Greg Mottola. The film stars Jesse Eisenberg, Kristen Stewart, Margarita Levieva, Ryan Reynolds, Martin Starr, Bill Hader, and Kristen Wiig.

It is the summer of 1987 and James Brennan (Jesse Eisenberg), a virgin, has just graduated with a degree in comparative literature from Oberlin College. He is looking forward to touring Europe for the summer and going to Columbia University for graduate school in journalism, when his parents (Wendie Malick and Jack Gilpin) announce they won't be able to help him financially. James searches for a summer job, but can only find an unappealing one at Adventureland, a local amusement park in his hometown of Pittsburgh, Pennsylvania, where his immature childhood friend Tommy Frigo (Matt Bush) works. James is hired by assistant manager Bobby (Bill Hader) and is assigned to the games area. He meets his co-workers: the sarcastic Joel (Martin Starr), Bobby's wife and park manager Paulette (Kristen Wiig), Sue O'Malley (Paige Howard), Mark (Mark Miller), the alluring Lisa P. (Margarita Levieva) whom every guy wants, and the park's technician Mike Connell (Ryan Reynolds), a part-time musician. Another games worker, Emily "Em" Lewin (Kristen Stewart), meets James by saving him from being stabbed by a disgruntled customer. While her father and stepmother are away, Em has a party where she and James get to know each other. After the party, Connell, who has been having an affair with Em, comes over to further pursue the affair. Later that week, James goes for a drink with Em and she is surprised to learn James has never had sex. After leaving, James and Em share their first kiss. The following day, James tells Connell about his strong feelings for Em, which Connell reports to her. Em later tells James that she wants to take things slow due to problems in her life, leaving James feeling confused and upset. Joel is rejected by Sue after a drunken night of making out due to religious differences (she is Catholic and he is Jewish). Lisa P. asks James out on a date, but he has mixed feelings because of his relationship with Em. After Connell talks him into going, presumably to sabotage James' relationship with Em, he decides to accept her offer. After the date, during which Lisa and James kiss, James learns Em had called to tell him that she regrets having rejected his feelings. James gives Em some of his marijuana to bake pot cookies to cheer her up. Joel later sees James and Em walking together and, disturbed by the whole chain of events, decides to quit. James tries to talk him out of quitting, but Joel has had enough of it all. He also tells James he is angry at him for dating Lisa P. when he already loves Em. Wanting to be honest, James tells Em about going out with Lisa P. After hearing of this, Em goes to Connell's to end their affair. Prompted by Frigo, the park's mentally-challenged parking official tells James he saw Em and Connell doing "push-ups without any pants on" in the back of Connell's car. James goes to Connell's mother's house, which is where Lisa P. told him that Connell takes girls to have sex, and sees Em leaving. Shocked to see James, Em becomes tongue-tied and cannot explain. James leaves angrily, leaving a crying Em by herself. James tells Lisa P. about the affair and asks her not to tell anyone, but not long after, she tells her friend Kelly. Upon noticing that all the park employees know, Em quits. James chastises Lisa P. for dismissing Em as a "homewrecker" while seeing Connell as blameless. Heartbroken, he drunkenly crashes his dad's car into a tree and passes out. The next morning, his mother wakes him up and tells him that he has to pay to fix the damage. Because he must pay for the car, James doesn't have enough money to go to graduate school. Despite his setbacks, he heads for New York City with his parents blessing, as they finally decide that it's time to let James do what is best for him. In New York, James waits outside Em's apartment. She is reluctant to talk to him, feeling she has ruined everything. James tells her that he sees her in a different way from the way she sees herself, making it clear that he has fallen in love with her. Touched, Em brings James up to her apartment. James reveals he is not going to Columbia this year, and considers next year. He gets out of his wet clothes and finds that Em still has an Adventureland shirt. They kiss and begin to take their clothes off. James asks, "Are we really doing this?", and Em says yes; James presumably loses his virginity.