When you compare a rom-com like Playing It Cool to 500 Days of Summer, it seems like the younger sibling who earnestly tries to be like the older brother who’s good at everything, but always lags behind. Directed by Justin Reardon, Playing It Cool is a rom-com alright, but it seems to lack in more than a few places. The film is about a Hollywood screenwriter (he doesn’t have a name, he’s credited as Him in the credits), who has the overly-used writer’s block, played by Chris Evans. Things get interesting when his agent, played by Anthony Mackie, offers him a chance to write a rom-com screenplay. However, Evans’ character has never fallen in love in his life, because his mother left him when he was a child and now, he’s damaged goods. Writing a rom-com seems difficult for the man who doesn’t believe in love and considers it to be a sham, but then, he meets a beautiful woman (played by Michelle Monaghan), who makes him fall head over heels in love with her.
Everything seems rosy for a moment- all he has to do is go over, turn on the charm, buy her a drink and tell her he likes her. Except that she has a fiancé (Ioan Gruffudd). Evans seeks help from his fellow writer friends- all of whom are the clichéd pals- a gay best friend (Topher Grace), a self confessed man hater (Aubrey Plaza), a disgruntled husband (Luke Wilson) and a misogynistic ladies man (Anthony Mackie), but they all seem to have problems of their own. What really brings the film down is the way it tells the story. Chris Evans’ character narrates, and Reardon tries to fuse fantasy, flashbacks, voiceovers and history into a single narrative. Although they’re all really well done individually, together they become a tad distracting. With a weak resolution, the plot has some obvious holes. The clichés are glaring- there’s a running through an airport scene, the reformed bad boy, and a lot more. But there’s a good side too. There’s a couple of witty jokes packed in the story; the scene with Evans and his friends making double entendres about old authors is especially funny. Monaghan and Evans have chemistry and seem like a regular couple who have their own problems. Why Should You Watch the Film: The lead pair share a good dynamic on-screen, and Evans is convincing as the regular guy next door. Parts of the film are funny and quirky, making it amusing and engaging. Catch it with a loved one over the weekend!