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.
Top Cast
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
Photos
Reviews
Loading reviews…
More Like This
My Favorite Wife
17 May 1940
Yes Man
09 Dec 2008
People We Meet on Vacation
06 Jan 2026
What Happens in Vegas
07 May 2008
It Happened One Night
22 Feb 1934
Valentine's Day
10 Feb 2010
The Wrong Paris
11 Sep 2025
Think Like a Man Too
20 Jun 2014
Yoh! Bestie
06 Feb 2026
The Philadelphia Story
05 Dec 1940
Six Days Seven Nights
12 Jun 1998
Merv
09 Dec 2025
Everyone Says I Love You
06 Dec 1996
Relationship Goals
04 Feb 2026
Keeping the Faith
14 Apr 2000
Crossing Delancey
17 Aug 1988
Wedding Crashers
13 Jul 2005
Move Over, Darling
19 Dec 1963
Little Italy
24 Aug 2018
Pretty Woman
23 Mar 1990