She tells him she isn't sure, and that she doesn't want to become too comfortable there again. Serena confronts him about him having sex with Jennifer, and he asks her if she's planning on staying in Portland. He flees to the rooftop, where he finds Serena sitting alone. Several days later, David attends a 1980s-themed party with Jennifer, Robert, and Tony, which is busted by police. The two return the next day, but Serena is disheartened soon after when she discovers David and Jennifer having sex. The following day, she confesses to Jennifer she wants to return to Portland. In New York, Serena and Jennifer attend a party, where Serena is date raped. While Mary marches through the woods with Devlin, David has a hallucination in which his deceased mother brings him lunch. While hiking with Mary, David runs into his friend Devlin (Jack Black), who is running a spiritual retreat in the woods, where they partake in LSD. In Portland, David begins a romance with Mary, and moves in with Robert, Tony, and Jennifer. She meets Bobby (Scott Caan) one afternoon in a diner, and he invites her to move in with him in his apartment, which she discovers is actually a squat in the East Village. In New York, Serena becomes increasingly frustrated with Tommy's paranoid antics. Before she leaves, she and David get into a fight, which ends in her burning down his house. Serena becomes frustrated with David's lack of ambition, and decides to move to New York City with Tommy (Jamie Kennedy), a punk rocker and paranoid heroin addict. After moving into his house, she introduces him to Mary Weiss (Brittany Murphy), the daughter of a local gallery owner who falsely claims to be an art curator. Serena develops a liking to David after seeing the artwork he does in his spare time, and encourages him to make a career for himself. After having previously sold marijuana to a woman named Jennifer (Amy Locane), he is introduced to her friend, the tempestuous Serena (Alicia Witt), who is immediately disliked by his friends, Robert (Jeremy Sisto) and Tony (Andy Dick), a gay couple. David (Luke Wilson) is a stoner living in Portland, Oregon.
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