Victor Mancini (SAM ROCKWELL) is one screwed-up fellow. He's employed as a historical reenactor at a colonial theme park where he works with his best friend, Denny (BRAD WILLIAM HENKE), for their boss and fellow actor Charlie (CLARK GREGG) who never goes out of character, all while lusting after Ursula (BIJOU PHILLIPS) who poses as the period milkmaid.
The craving isn't unusual for Victor, a self-proclaimed sex addict who attends support meetings with Denny, a compulsive masturbator, but often skips out to have sex with the likes of hooker Nico (PAZ DE LA HUERTA). To top it off, Victor repeatedly gets himself to choke in restaurants so that handpicked and seemingly financially well-to-do strangers will save his life and then send him money.
While it's all a con, Victor spends most of that money to keep his mother, Ida (ANJELICA HUSTON), cared for in a mental institution. Since she was certainly anything but a perfect mom when young Victor (JONAH BOBO) was just a boy and he moved from one foster home to another when not on the lam with her, he's nebulous about her declining health. Yet, she has a psychological hold on Victor -- even if she usually thinks he's someone else when he visits -- a point not lost on her new doctor, Paige Marshall (KELLY MACDONALD).
Victor is fascinated by this young woman -- especially when she concocts a unique way to try to help Ida's progressively worsening dementia -- but finds himself unable to consummate his attraction to her. As Denny similarly finds himself attracted to Beth (GILLIAN JACOBS), a stripper who goes by the stage name Cherry Daiquiri, Victor tries to sort out his feelings toward both his mother and Paige.