![Playing It Cool](https://image.tmdb.org/t/p/original//zY75ms36ypIQxFAFLtoYfNFuSD7.jpg)
![Playing It Cool](https://image.tmdb.org/t/p/w200//4B2FLN0c2vY6im3Oe2ZkYftulmq.jpg)
Playing It Cool
1 hour 34 minutes2014-09-26
5.9
Watch Trailer
A young man meets and instantly falls in love with an engaged woman.
Cast
![Chris Evans](https://image.tmdb.org/t/p/w200//3bOGNsHlrswhyW79uvIHH1V43JI.jpg)
Chris Evans
Narrator
![Michelle Monaghan](https://image.tmdb.org/t/p/w200//jB47BoGdudHELszn9ZAZqnnUy8N.jpg)
Michelle Monaghan
Her
![Topher Grace](https://image.tmdb.org/t/p/w200//hvXoqAKI958higegGERDLKaLhj8.jpg)
Topher Grace
Scott
![Aubrey Plaza](https://image.tmdb.org/t/p/w200//6qeCvOF1K88nKqZfzaWYESo0CwW.jpg)
Aubrey Plaza
Mallory
![Luke Wilson](https://image.tmdb.org/t/p/w200//ul2scyx803VR5WeY9BnTup3mpEY.jpg)
Luke Wilson
Samson
![Martin Starr](https://image.tmdb.org/t/p/w200//gNyCdend3C5gY3ucq42Zt3swfg2.jpg)
Martin Starr
Lyle
![Anthony Mackie](https://image.tmdb.org/t/p/w200//kfTwOYr3iUucmYz8kPjhYy07G2Z.jpg)
Anthony Mackie
Bryan
![Ioan Gruffudd](https://image.tmdb.org/t/p/w200//8fZ1h879lO5lcKt9SG2UIXisq1k.jpg)
Ioan Gruffudd
Stuffy
![Philip Baker Hall](https://image.tmdb.org/t/p/w200//ef7M9soBIv6iGnGEiCdsQ6ppjFl.jpg)
Philip Baker Hall
Granddad
![Patrick Warburton](https://image.tmdb.org/t/p/w200//eLqDtbFYmlTxov9vT9Dwldn839v.jpg)
Patrick Warburton
Dick
![Ashley Tisdale](https://image.tmdb.org/t/p/w200//ot6ib67jxvKVG1JCBl0ROPGtdeP.jpg)
Ashley Tisdale
Ashley Tisdale
![Matthew Morrison](https://image.tmdb.org/t/p/w200//u3CA6kqhpPVhK3zLD7yW0UfCyWt.jpg)
Matthew Morrison
Matthew Morrison
![Jaeden Martell](https://image.tmdb.org/t/p/w200//Anx0n2hsJnHKAnMQP7ptOTfTxTI.jpg)
Jaeden Martell
6 Year Old Me
![Fabianne Therese](https://image.tmdb.org/t/p/w200//w1ES3wqpERfngz7DVujVMSpLZ04.jpg)
Fabianne Therese
College Girl
![Gerry Bednob](https://image.tmdb.org/t/p/w200//aO2tNxVdnB8hVgTiK8BLW9TrKms.jpg)
Gerry Bednob
Cabbie / Gabriel
![Beverly D'Angelo](https://image.tmdb.org/t/p/w200//8fYQIA8dAaA4GOTxOFSKIvTqzi.jpg)
Beverly D'Angelo
Lyle's Girlfriend
![Kyle Mooney](https://image.tmdb.org/t/p/w200//xywmFOt1OkUGa2Ex2YnmjI6gyd7.jpg)
Kyle Mooney
Other Dude
![Scott Evans](https://image.tmdb.org/t/p/w200//x4tX5FmEBInEWTo0mFZkPU6fIqq.jpg)
Scott Evans
Blissful Boy
![Brenda Schmid](https://image.tmdb.org/t/p/w200//pLWh0gowHZ76Tky0o7wEtJEzbgj.jpg)
Brenda Schmid
Blissful Girl
![Sarah Dumont](https://image.tmdb.org/t/p/w200//lW6Qxv5OYfHxdwy7UIalIjpdL07.jpg)
Sarah Dumont
Cute Girl
![Mikaela Hoover](https://image.tmdb.org/t/p/w200//vH7XYI6cw6PFRDflOJY8iQEEg7g.jpg)
Mikaela Hoover
Lacey
![Devon Ogden](https://image.tmdb.org/t/p/w200//gsAX6mzrj6inqXSe4jOfSObysU3.jpg)