
“Playing It Cool” sees Evans falls hard for a woman who is already engaged, played by Michelle Monaghan. Evans plays a writer who has been disillusioned by love until he meets Her (Monaghan) at a charity dinner. But He (Evans) pursues her and tries to deal with a platonic relationship just to keep seeing Her – stopping at nothing to conquer her heart.

Using the power of his imagination, the writer tries to conquer "Her" heart where Anthony Mackie, Aubrey Plaza, Ashley Tisdale, Patrick Warburton, Giovanni Ribisi, Topher Grace, Ioan Gruffudd and Luke Wilson round up an interesting ensemble cast under Justin Reardon’s direction.

Chris Evans and Michelle Monaghan have really complicated feelings in the film. Making him fall for her, not knowing at first that it will be all unrequited love for she is already engaged to someone else. What makes it more complicated is that, the Narrator does not believe in love and commitment until he met and known her along the way that they have been together. The movie depicts the usual setup of lovers around the globe; the love that has been unrequited by someone else and a lot more complicated issues why two people can't be together in a more evident and apparent reason.
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