Playing It Cool 2014 · USA · 94 minutes · R · romantic comedy Stars: Chris Evans, Michelle Monaghan, Aubrey Plaza Director: Justin Reardon Love... it's a balancing act Unrequited love motivates a guy to write about his experiences. Tags: otherwise engaged 5.9 / 10 Login to add your rating Have you seen it? Add to your watchlist Like Love... it's a balancing act Unrequited love motivates a guy to write about his experiences. Tags: otherwise engaged Watch Playing It Cool trailer Starring of Playing It Cool Chris Evans as Narrator Michelle Monaghan as Her Aubrey Plaza as Mallory Ioan Gruffudd as Stuffy Martin Starr as Lyle Ashley Tisdale as Ashley Tisdale Patrick Warburton as Dick Topher Grace as Scott Anthony Mackie as Bryan Luke Wilson as Samson Jaeden Lieberher as 6 Year Old Me Philip Baker Hall as Granddad Fabianne Therese as College Girl Storyline of Playing It Cool The story of a young man disillusioned by love who meets a breathtaking young woman at a charity dinner by pretending to be a philanthropist. Turns out that she’s engaged to a guy who doesn’t like her going on dates. Challenged by the chase, and egged on by his eclectic friends, he feigns a platonic relationship in order to keep seeing her as he tries to conquer her heart Genre: comedy, romance Theme: otherwise engaged Certification: Mature Audiences - Ages 17+ Recommended Flag: profanity, sexual situations MPA rating: R Rating of Playing It Cool 5.9 / 10 Login to add your rating Have you seen it? Add to your watchlist Like 0 0 0 0 0 Reviews of Playing It Cool Write your review or comment