Movie

Playing It Cool

“Love... it's a balancing act”

★ 5.8(811)20141h 34m

Playing It Cool is streaming on Amazon Prime Video and Amazon Prime Video with Ads in Canada, and available to rent or buy on CosmoGo and Amazon Video. Availability checked 14 June 2026.

Where to watch Playing It Cool

🇨🇦 Canada

Amazon Prime VideoStream

Amazon Prime Video with AdsStream

Good to know

Director: Justin Reardon
Release date: 2014-09-26
Runtime: 1h 34m
Language: English
Box office: $1,323,415
Status: Released
Country: United States of America
Studio: Wonderland Sound and Vision

Playing It Cool — trailer

About Playing It Cool

Playing It Cool is a 2014 movie in the Comedy and Romance genres, directed by Justin Reardon, starring Chris Evans, Michelle Monaghan and Topher Grace. It has a runtime of 1 hour 34 minutes. It holds an average rating of 5.8/10 from 811 viewers. Below you can see where to watch Playing It Cool in Canada — across streaming, rental and purchase options — along with the full cast, trailer and viewer reviews.

Synopsis

A young man meets and instantly falls in love with an engaged woman.

Cast

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 French

Ashley Tisdale

Matthew Morrison

Themes & keywords

screenwriterromcomromancelovefriendslos angeles, californialyingengagedamused

Frequently asked questions

Where can I watch Playing It Cool in Canada?+

In Canada, you can stream Playing It Cool on Amazon Prime Video and Amazon Prime Video with Ads. It's also available to rent or buy on CosmoGo and Amazon Video.

Is Playing It Cool on Netflix?+

Playing It Cool is not on Netflix in Canada right now, but you can stream it on Amazon Prime Video and Amazon Prime Video with Ads.

How long is Playing It Cool?+

Playing It Cool has a runtime of 1 hour 34 minutes (94 minutes).

Who stars in Playing It Cool?+

Playing It Cool stars Chris Evans, Michelle Monaghan, Topher Grace, Aubrey Plaza and Luke Wilson.

When did Playing It Cool come out?+

Playing It Cool is a 2014 movie directed by Justin Reardon.

What genre is Playing It Cool?+

Playing It Cool is Comedy and Romance film.

Who directed Playing It Cool?+

Playing It Cool was directed by Justin Reardon.