Picking up the pieces of his life after his wife dumps him, Reuben Feffer (Ben Stiller) is hindered rather than helped by his best friend Sandy Lyle (Philip Seymour Hoffman), a child acting star who bitterly lives off his past glory. When he bumps into old schoolmate Polly Prince (Jennifer Aniston), a free spirit who never met a risk she didn't want to take, Reuben sees a second chance at love and a first at a more intrepid life.