Oregon pot dealer David (Luke Wilson) is perfectly happy with his uninspired artwork and sonambulstic slacker life. Along wih his layabout gay friends -- Tony (Andy Dick) and Robert (Jeremy Sisto) -- David seems to have no worries as long as the marijuana crop keeps coming in. But a social hitchhiker named Serena (Alicia Witt) finds her way into David's life and a relationship staggers to full blossom. As David gets more serious about his art, thanks to Serena's encouragement, Serena leaves to try out the rock 'n' roll life of New York City. David numbs his feelings for Serena with meaningless sex with her friend Mary (Brittany Murphy) and a wild mushroom-induced adventure in the woods with Jennifer (Amy Locane) and a zany drug guru Devlin (Jack Black). Meanwhile, Serena gets a brutal wakeup call about life in the big city and returns home to David. But is that the best thing for both of them?