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The Third Wheel (2002)

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Storyline:
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.
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Luke Wilson as Stanley
Denise Richards as Diana Evans
Jay Lacopo as Phil
Ben Affleck as Michael
Phill Lewis as Mitch
Deborah Theaker as Nancy
Melissa McCarthy as Marilyn
Tim DeKay as Speaker
Greg Pitts as Tee
Wayne Federman as Glen Federman
Mike Schwartz as Co-Worker
Neal Matarazzo as Neal
Jim Lau as Clerk
Diana-Maria Riva as Rose Lady
Blas Lorenzo as Waiter
Full cast
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