For the most cautious man on Earth, life is about to get interesting.
Ben Stiller
Reuben Feffer
Jennifer Aniston
Polly Prince
Philip Seymour Hoffman
Sandy Lyle
Debra Messing
Lisa Kramer
Alec Baldwin
Stan Indursky
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.
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Hank Azaria
Claude
Bryan Brown
Leland Van Lew
Jsu Garcia
Javier
Michele Lee
Vivian Feffer
Bob Dishy
Irving Feffer
Missi Pyle
Roxanne
Judah Friedlander
Dustin
Kevin Hart
Vic
Masi Oka
Wonsuk
Kym Whitley
Gladys
Amy Hohn
Cheryl
Nathan Dean
Mitch
Cheryl Hines
Catering Manager
Caroline Aaron
Wedding Coordinator
Christina Kirk
Party Hostess
Todd Stashwick
Security Officer
Robb Skyler
Basketball Player
Edward Conna
Basketball Player
Bruce Nozick
Executive Chef
The Salsa King
Clip · YouTube
Along Came Polly Trailer
Trailer · YouTube
