Gabriel Noone (ROBIN WILLIAMS) is a late-night talk radio personality who often discusses his personal experiences on air. That includes his recent break-up with his longtime gay lover, Jess (BOBBY CANNAVALE), who's had enough of Gabriel's inability to separate his personal and professional lives.
Accordingly, Gabriel has focused his energies on an out of town, teenage fan of his show, Pete (RORY CULKIN), who's looking to publish a book about his troubled upbringing, including child abuse, a bout with syphilis and now a terminal case of AIDS. When Pete's too tired to talk, his doting mom, Donna (TONI COLLETTE), stands in for him, informing Gabriel of what's occurring in their lives.
Gabriel hopes to see them over Christmas and get publisher Ashe (JOE MORTON) to work with Pete's manuscript, but Jess plants a seed of doubt when he informs his ex that he thinks Pete and Donna are the same person. When that Christmas trip is canceled, Gabriel begins to have his own suspicions. With the aide of his friend Anna (SANDRA OH), he then starts trying to figure out if Jess' statement is true, an investigation that soon learns to some startling discoveries.