Playing It Cool poster
Where to stream

Playing It Cool

5.920141h 34m14AMovieComedyRomance

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

DirectorJustin Reardon
WritersPaul Vicknair·Chris Shafer
ProducersChris Evans·Nicolas Chartier

Where to watch

Amazon Prime VideoAmazon Prime VideoAmazon Prime Video with AdsAmazon Prime Video with AdsHooplaHooplaTubi TVTubi TVPlexPlexPluto TVPluto TV
Availability shown for Canada · rights vary by country

Cast · Directed by Justin Reardon

CEChris Evans
Chris Evans
Narrator
MMMichelle Monaghan
Michelle Monaghan
Her
TGTopher Grace
Topher Grace
Scott
APAubrey Plaza
Aubrey Plaza
Mallory
LWLuke Wilson
Luke Wilson
Samson
MSMartin Starr
Martin Starr
Lyle
AMAnthony Mackie
Anthony Mackie
Bryan
IGIoan Gruffudd
Ioan Gruffudd
Stuffy
PHPhilip Baker Hall
Philip Baker Hall
Granddad
PWPatrick Warburton
Patrick Warburton
Dick
AFAshley French
Ashley French
Ashley Tisdale
MMMatthew Morrison
Matthew Morrison
Matthew Morrison

More from Chris Evans · Lead actor

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See all fromChris Evans

More from Michelle Monaghan · Co-star actress

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Source Code
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Boston Public
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Playing It Cool — streaming FAQ

Which OTT platform streams Playing It Cool?

Playing It Cool is streaming on Amazon Prime Video, Hoopla and Tubi TV in Canada, and available to rent or buy on CosmoGo and Amazon Video. It's not currently on Netflix.

Is Playing It Cool on Netflix?

No, Playing It Cool is not on Netflix in Canada as of September 2026. It's currently on Amazon Prime Video and Hoopla.

Is Playing It Cool on Amazon Prime Video?

Yes — Playing It Cool is included with an Amazon Prime Video subscription in Canada as of September 2026.

Where can I watch Playing It Cool for free?

Playing It Cool is available to stream free (with ads) on Hoopla and Tubi TV in Canada.