Playing It Cool (2014)
R
94 min | Comedy, Romance

Unrequited love motivates a guy to write about his experiences.
Read more: Plot summary
Writers
Chris Shafer (screenplay) | Paul Vicknair (screenplay)
Composer
Cinematographer
Casting Director
Production Designer
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Release date
May 8, 2015 (United States)

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Cast

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84 cast members
Name Known for
Aubrey Plaza
Mallory Mallory   See fewer
Luke Wilson
Samson Samson   See fewer
Ioan Gruffudd
Stuffy Stuffy   See fewer
Philip Baker Hall
Granddad Granddad   See fewer
Patrick Warburton
Hedge Funder Hedge Funder   See fewer
Gerry Bednob
Cabbie / Gabriel Cabbie / Gabriel   See fewer
L. Peter Callender
Tourist Couple Guy Tourist Couple Guy   See fewer
Velina Brown
Tourist Couple Girl Tourist Couple Girl   See fewer
Ryan Cover
Skateboarder Skateboarder   See fewer
Peyton List
Hot Girl Hot Girl   See fewer
Kyle Mooney
Other Dude Other Dude   See fewer
Sarah Dumont
Cute Girl Cute Girl   See fewer
Shelly Slocum
Samson's Wife Samson's Wife   See fewer
Matthew Morrison
Matthew Morrison (as Matthew J. Morrison) Matthew Morrison (as Matthew J. Morrison)   See fewer
Ashley Tisdale
Ashley Tisdale Ashley Tisdale   See fewer
Beverly D'Angelo
Lyle's Girlfriend (as Beverly D'Angleo) Lyle's Girlfriend (as Beverly D'Angleo)   See fewer
Brenda Schmid
Blissful Girl Blissful Girl   See fewer
Scott Evans
Blissful Boy Blissful Boy   See fewer
Precious Chong
Serious Girl Serious Girl   See fewer
Thomas R. Martin
Serious Guy Serious Guy   See fewer
Tony Cavalero
Charity Waiter Charity Waiter   See fewer
Catero Colbert
Diner Waiter Diner Waiter   See fewer
Kelsey McNamee
Charity Event Hostess (as Kelsey Mcnamee) Charity Event Hostess (as Kelsey Mcnamee)   See fewer
Abby Ryder Fortson
Little Girl (as Abby Ryger Fortson) Little Girl (as Abby Ryger Fortson)   See fewer
Sean Carrigan
Another Guy Another Guy   See fewer
Petie Sjogren
Teenage Girl Teenage Girl   See fewer
Lara Everly
Girl Next Door Girl Next Door   See fewer
Jeremy Glazer
New Guy New Guy   See fewer
Fabianne Therese
College Girl College Girl   See fewer
Carl McDowell
Neighbor (as Carl Mcdowell) Neighbor (as Carl Mcdowell)   See fewer
Shantel Wislawski
Supermodel Supermodel   See fewer
Michael X. Sommers
San Francisco Bystander (as Michael Sommers) San Francisco Bystander (as Michael Sommers)   See fewer
Nicholas Bearde
Man From Crowd (as Nicolas Bearde) Man From Crowd (as Nicolas Bearde)   See fewer
Jaeden Martell
6 Year Old Me (as Jaeden Lieberher) 6 Year Old Me (as Jaeden Lieberher)   See fewer
Carmina Garay
6 Year Old Girl 6 Year Old Girl   See fewer
Joey Capone
Abrasive Clerk Abrasive Clerk   See fewer
Kahyun Kim
Korean Woman Korean Woman   See fewer
Jason S. Kim
Korean Man Korean Man   See fewer
Cathy Tanaka
Hipster Chick Hipster Chick   See fewer
Jaden Alexander
Photographer (uncredited) Photographer (uncredited)   See fewer
Natalie Marie Ames
Charity Event Guest (uncredited) Charity Event Guest (uncredited)   See fewer
Joseph Aviel
Beach Bodybuilder (uncredited) Beach Bodybuilder (uncredited)   See fewer
Drew Benda
Tourist (uncredited) Tourist (uncredited)   See fewer
Julie Berlin
Party Guest (uncredited) Party Guest (uncredited)   See fewer
Cici Leah Campbell
Medieval English Peasant (uncredited) Medieval English Peasant (uncredited)   See fewer
Dwight V Coleman
Beach Camper (uncredited) Beach Camper (uncredited)   See fewer
Joshua Corley
Bartender (uncredited) Bartender (uncredited)   See fewer
Thomas Dalby
The Groundskeeper (uncredited) The Groundskeeper (uncredited)   See fewer
Sandra Daubert
Valentino Woman (uncredited) Valentino Woman (uncredited)   See fewer
Rick L. Dean
Charity Event Guest (uncredited) Charity Event Guest (uncredited)   See fewer
Alexandra Fatovich
Maid of Honor (uncredited) Maid of Honor (uncredited)   See fewer
Theodore John Forsi
Artist at Gallery (uncredited) Artist at Gallery (uncredited)   See fewer
Geoffrey Gould
Pedestrian (uncredited) Pedestrian (uncredited)   See fewer
Jon Robert Hall
Bartender (uncredited) Bartender (uncredited)   See fewer
Matt Harding
Diner Cook (uncredited) Diner Cook (uncredited)   See fewer
Nicky Hawthorne
Cocktail Waitress (uncredited) Cocktail Waitress (uncredited)   See fewer
Pamela Keith
Wealthy Woman (uncredited) Wealthy Woman (uncredited)   See fewer
Nate Komari
Skateboarder (uncredited) Skateboarder (uncredited)   See fewer
Mark Lavell
Businessman (uncredited) Businessman (uncredited)   See fewer
Charley Lodi
Gun Club Employee (uncredited) Gun Club Employee (uncredited)   See fewer
Carly Louis
Babysitter (uncredited) Babysitter (uncredited)   See fewer
Phil Mallon
Bar Patron (uncredited) Bar Patron (uncredited)   See fewer
Mahal Montoya
Casual Traveller (uncredited) Casual Traveller (uncredited)   See fewer
Marcus Natividad
Dax (uncredited) Dax (uncredited)   See fewer
Tamim Nawabi
Skateboarder (uncredited) Skateboarder (uncredited)   See fewer
Dennis Nicomede
Charity Event Guest (uncredited) Charity Event Guest (uncredited)   See fewer
Onrico Nightingale
Guy at Bar with Drink (uncredited) Guy at Bar with Drink (uncredited)   See fewer
Nkechi
Tourist (uncredited) Tourist (uncredited)   See fewer
Rajiv Shah
Tourist (uncredited) Tourist (uncredited)   See fewer
Sharelle Smith
Runner (uncredited) Runner (uncredited)   See fewer
Luci Suicide
Suicide Girl (uncredited) Suicide Girl (uncredited)   See fewer
Joseph Lyle Taylor
Priest (uncredited) Priest (uncredited)   See fewer
Oliver Trevena
The Best Man (uncredited) The Best Man (uncredited)   See fewer
James D. Weston II
Tourist (uncredited) Tourist (uncredited)   See fewer
Anthony James Whitewolf
Waitstaff (uncredited) Waitstaff (uncredited)   See fewer
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