Comedy / Romance /

Score: 51.9%( 119 votes )

Overview: The clumsy and shy Stanley is a nice fellow, beloved by his colleagues in the office. He has a crush on the gorgeous new-hire Diana, but he has difficulties to get close to her. When Stanley finally invites Diana for a date, he hits the homeless Phil with his Taurus, and his planned night turns upside down.

Cast:

Luke Wilson
Stanley

Denise Richards
Diana

Jay Lacopo
Phil

Ben Affleck
Michael

Phill Lewis
Mitch

Deborah Theaker
Nancy

Melissa McCarthy
Marilyn

Tim DeKay
Speaker

Greg Pitts
Tee

Wayne Federman
Glen Federman

Mike Schwartz
Co-Worker

Neal Matarazzo
Neal

Jim Lau
Clerk

Diana Maria Riva
Rose Lady

Blas Lorenzo
Waiter

Buck Kartalian
Old Man

Rachel Winfree
Knitting Lady

Robert M. Koch
Actor (Lincoln)

Jason Kravits
Stage Manager

Jeanette Miller
Elderly Woman

Kevin Farley
Bus Driver

Marcus DeJohn
Bill

Marilyn Staley
Mary

Veena Bidasha
Mahareinlu

David Koechner
Carl

Matthew Maher
Hank

Meredith Salenger
Sara

Bobby Slayton
Dave Bowen

Phil Reeves
Bill Sykes

Steven Shenbaum
Ted

Joan Blair
Woman On the Bus (uncredited)

Amy Boatwright
Waitress (uncredited)

Matt Damon
Kevin (uncredited)

Jeff Garlin
Office Worker (uncredited)

Joy Gohring
Drunk Office Girl (uncredited)

Lauren Graham
Woman at the Party (uncredited)

Marcus Johnson
Bill (uncredited)

Richie Keen
Rich (uncredited)

Dan Paragon
Guy Arguing (uncredited)

Marcio Rosario
Lorenzo (uncredited)

Nicole Sullivan
Sally (uncredited)