Playing It Cool poster
Where to stream

Playing It Cool

5.920141h 34mRMovieComedyRomance

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

HooplaHooplaFawesomeFawesomeThe Roku ChannelThe Roku ChannelFandango at Home FreeFandango at Home FreeTubi TVTubi TV
Availability shown for United States · 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

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More from Michelle Monaghan · Co-star actress

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Playing It Cool — streaming FAQ

Which OTT platform streams Playing It Cool?

Playing It Cool is streaming on Hoopla, Fawesome and The Roku Channel in United States, and available to rent or buy on Amazon Video and Fandango At Home. It's not currently on Netflix.

Is Playing It Cool on Netflix?

No, Playing It Cool is not on Netflix in United States as of October 2026. It's currently on Hoopla and Fawesome.

Is Playing It Cool on Amazon Prime Video?

Playing It Cool isn't included with a Prime Video subscription in United States, but you can rent or buy it on Amazon Video.

Where can I watch Playing It Cool for free?

Playing It Cool is available to stream free (with ads) on Hoopla and Fawesome in United States.