The Third Wheel

The only thing Stanley & Michael didn't plan on for the perfect date was... Phil.

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.

Comedy Romance

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))