Playing It Cool is a smart, sexy and very funny modern comedy with a star studded cast guaranteed to make you believe in true love. Chris Evans plays a screenwriter who wants to write action movies, but his agent is insisting he first writes a romance. The only problem is that he doesn't believe in love and hates the idea of commitment. When he meets Michelle Monaghan he thinks that she may be the one to change his opinion and help him write about love, until he finds out she is engaged. Can he overcome his fear of commitment and lack of romantic experience to win her heart?