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Playing It Cool poster

MOVIE · 2014

Playing It Cool

ComedyRomance94 min

An emotionally blocked screenwriter talks a big game about love until a charity dinner puts him face to face with a woman he can’t stop thinking about, and she’s already engaged. Chris Evans is the commitment-averse writer at the center of it, while Michelle Monaghan’s stranger becomes both his inspiration and his complication. The two try to keep their connection strictly platonic, but his running commentary and elaborate daydreams keep turning every encounter into a romantic scenario he can’t quite control. As their friendship deepens, the film keeps circling the gap between what he says about love and what he actually wants.

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Catalogue checked October 30, 2026. Use ReelRecs with an assistant