Playing It Cool Love... it's a balancing act A young man meets and instantly falls in love with an engaged woman. Details Casts Videos Galleries Posters Title Playing It Cool Release Date 2014-09-26 Runtime 01 Hours 34 Minutes Genres Comedy Romance Production Companies Wonderland Sound and Vision, Voltage Pictures Production Countries United States of America Chris Evans... Narrator... Michelle Monaghan... Her... Topher Grace... Scott... Aubrey Plaza... Mallory... Luke Wilson... Samson... Martin Starr... Lyle... Anthony Mackie... Bryan... Ioan Gruffudd... Stuffy... Philip Baker Hall... Granddad... Patrick Warburton... Dick... Ashley Tisdale... Ashley Tisdale... Matthew Morrison... Matthew Morrison... Jaeden Martell... 6 Year Old Me... Fabianne Therese... College Girl... Gerry Bednob... Cabbie / Gabriel... Beverly D'Angelo... Lyle's Girlfriend... Kyle Mooney... Other Dude... Scott Evans... Blissful Boy... Brenda Schmid... Blissful Girl... Sarah Dumont... Cute Girl... Mikaela Hoover... Lacey... Devon Ogden... Sadie... Playing it Cool - Official Trailer #1 (2015) - Chris Evans Comedy Movie HD (Trailer) Original Size (1920x1080) Original Size (3000x1688) Original Size (2700x1519) Original Size (3840x2160) Original Size (1400x2100) Original Size (1400x2100) Original Size (1000x1500) Original Size (913x1361) Original Size (1192x1777) Original Size (1400x2100) Original Size (1365x2048) Original Size (1000x1500) Original Size (2000x3000) Original Size (2000x3000) Original Size (2000x3000) Original Size (1000x1500) Original Size (1000x1500) Original Size (1400x2100) Original Size (984x1476) Original Size (550x815) Original Size (600x854) Original Size (1000x1500) Original Size (913x1361) Original Size (1922x2865) Original Size (1365x2048) Original Size (700x1050) Original Size (1482x2208) Original Size (1400x2100)