Playing Cupid's primary photo
  • Playing Cupid (2008)
  • Unrated
    125 min | Comedy
Primary photo for Playing Cupid
Playing Cupid (2008)
Unrated
125 min | Comedy

Jeff and Keith are two of the luckiest guys you will ever meet. They have loving girlfriends, supportive friends and they're financially secure. NOT! They're trying to turn things around by starting their own dating service. Right when ...See moreJeff and Keith are two of the luckiest guys you will ever meet. They have loving girlfriends, supportive friends and they're financially secure. NOT! They're trying to turn things around by starting their own dating service. Right when things are looking up for them, everything comes crashing down when a familiar face from their past pays them a surprise visit. He wants them to hook him up with a former fat chick from high school, and he's willing to pay an exorbitant sum for them to do so. To make things worse, Keith forgets to keep business and pleasure separate, and things go astray. Can Keith and Jeff make business boom or will love get the best of them? Written by Anonymous See less
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Release date
Feb 14, 2008 (United States)

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Cast

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59 cast members
Name Known for
Daniel R. Quinn
Keith Atkins Keith Atkins   See fewer
Michael Ryan Redding
Jeff Shepherd Jeff Shepherd   See fewer
Brian J. Bentz
Ryan Chatham Ryan Chatham   See fewer
Simon D. Lorady
Seth Burton Seth Burton   See fewer
Amanda Newsham
Trish Casey Trish Casey   See fewer
Patrick Woodruff
Jake Tyler Jake Tyler   See fewer
Jesse Staples
Joe News Joe News   See fewer
Nick Waskie
Kilgore Kilgore   See fewer
Tim Alpaugh
Student #4 Student #4   See fewer
Zach Arce
Student #7 Student #7   See fewer
Damian Bartolacci
80s Party Guest 80s Party Guest   See fewer
James Bentz
80s Party Guest 80s Party Guest   See fewer
Kevin Bentz
Student #2 Student #2   See fewer
Matthew Bentz
Student #1 Student #1   See fewer
Will Bridge
Dinner Meeting Patron #3 Dinner Meeting Patron #3   See fewer
Leanne Brodnyan
Jessica Jessica   See fewer
Dana Castelli
Convinience Store Shopper #2 Convinience Store Shopper #2   See fewer
Guercine Dauphin
Blood Bank Receptionist Blood Bank Receptionist   See fewer
John Dunham
Student #10 (as John Duhnam) Student #10 (as John Duhnam)   See fewer
Derek Fields
Gay Dancer Gay Dancer   See fewer
Marqessa Gesualdi
80s Party Guest 80s Party Guest   See fewer
Robert Grissell
Dinner Meeting Patron #2 Dinner Meeting Patron #2   See fewer
Steve Jacobs
Dinner Meeting Patron #1 Dinner Meeting Patron #1   See fewer
Fredrick Johnson
Preston Preston   See fewer
Megan Jones
80s Party Guest 80s Party Guest   See fewer
Syed Kazmi
Convinience Store Clerk Convinience Store Clerk   See fewer
Leon Keefer
Leon Keefer Leon Keefer   See fewer
Jenna Kruscavage
Student #8 Student #8   See fewer
Chandra Lampreian
80s Party Guest 80s Party Guest   See fewer
Michael Leary
Cop #2 Cop #2   See fewer
Susan McConville
Student #9 Student #9   See fewer
Robert L. Mickles
Pat Kline Pat Kline   See fewer
Tara Mickles
Student #6 Student #6   See fewer
Robert Reed Murphy
Fr. Nelson Fr. Nelson   See fewer
Martin Myers
Dancer's Friend #1 Dancer's Friend #1   See fewer
Lee Nagy
80s Party Guest 80s Party Guest   See fewer
Eric M. Neiman
Convinience Store Shopper #1 Convinience Store Shopper #1   See fewer
Alexandra Padala
Nicole - The Sweatpants Nicole - The Sweatpants   See fewer
Melanie Penaranda
Student #3 Student #3   See fewer
John Piazza
Waiter Waiter   See fewer
Trevor Pillinger
80s Party Guest 80s Party Guest   See fewer
Kate Radicke
Barry's Girlfriend Barry's Girlfriend   See fewer
Jonathon Rola
Cop #1 Cop #1   See fewer
Chris Schewo
Bartender Bartender   See fewer
Eric Simmons
Julius Atkins Julius Atkins   See fewer
Dillon Simpson
Dancer's Friend #2 Dancer's Friend #2   See fewer
Bridgette Staples
Waitress Waitress   See fewer
Julian Staples
Cop #3 / Bum #1 Cop #3 / Bum #1   See fewer
Matt Stevens
Cop #4 Cop #4   See fewer
Kate Stillwagon
Jeff's Commercial Girlfriend Jeff's Commercial Girlfriend   See fewer
Lisa M. Winslow
80s Party Hot Girl 80s Party Hot Girl   See fewer
Joseph Young
Student #5 Student #5   See fewer
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