Reuben Feffer is a guy who's spent his entire life playing it safe. Polly Prince is irresistible as a free-spirit who lives for the thrill of the moment. When these two comically mismatched souls collide, Reuben's world is turned upside down, as he makes an uproarious attempt to change his life from middle-of-the-road to totally-out-there.
Ben Stiller
as Reuben Feffer
Jennifer Aniston
as Polly Prince
Philip Seymour Hoffman
as Sandy Lyle
Debra Messing
as Lisa Kramer
Alec Baldwin
as Stan Indursky
Hank Azaria
as Claude
Bryan Brown
as Leland Van Lew
Jsu Garcia
as Javier
Michele Lee
as Vivian Feffer
Bob Dishy
as Irving Feffer
Missi Pyle
as Roxanne
Judah Friedlander
as Dustin
