Buck O'Brien (Mike White (scriptwriter)) is a 27-year-old amateur playwright with the maturity level of an adolescent. When Buck's mother dies unexpectedly, he invites his close childhood friend Chuck (Chris Weitz) to the funeral. Chuck (who is now calling himself "Charlie") is a successful music industry exec with a fiancée, Carlyn (Beth Colt). He and Buck experimented sexually with each other when they were 11, but Charlie has repressed these memories and acts as if they had not occurred. Chuck had moved away while they were still children, and Buck has pined after him ever since. During their awkward reunion, Buck makes a sexual advance on Charlie in the bathroom. Charlie rebuffs him, and returns to Los Angeles with Carlyn, but not before extending an obligatory invitation for Buck to visit him there. Buck then withdraws $10,000 from his bank account, packs up his car, and takes up residence in a motel in Los Angeles. He also begins scripting a play on a yellow legal pad: titled "Hank and Frank and the Witch", it is an obvious plea for Charlie's love.