A screenwriter who doesn’t believe in love (Chris Evans) is tasked with writing a rom-com. As he struggles to put metaphorical pen to paper, he meets a woman (Michelle Monaghan) who he starts to have feelings for. It’s a pity she has a boyfriend but taking on the advice (both good and bad) from his eclectic group of writer friends, he tries to sort out his head and win her heart.
The two romantic leads in Playing It Cool are never actually give names so I’ll be referring to them by the actors’ surname to get through this review.
Playing It Cool is a rom com that likes to think it’s an anti-rom com but by the end it embraces a lot of the tropes, but it feels as if it is forced to do it rather than embracing it tongue and cheek. In some ways it reminded me of Isn’t It Romantic which poked fun at the tropes of rom coms, however unlike Isn’t It Romantic, Playing It Cool is often outright mean and treat the tropes and romance in general as something to be scorned. This comes from being told from Evans’ perspective and he’s jaded and shut off from romantic relationships. His actions come across quite bitter and having a lead that’s so self-centred doesn’t really make you root for him.
His best friend Scott (Topher Grace) loves romance. He’s an old fashioned romantic, a much nicer person and someone who is much more engaging on their quest for love. In fact, the glimpses we get of Evans’ writer friends make them seem all the more real and relatable than the main character.
Evans and Monaghan do have chemistry and it’s easy to be caught up in that when they’re on screen together. However, both of their characters are not good people and are frustrating to watch. He chases her when he knows she has a boyfriend; she is happy to cheat on her boyfriend and they both lie. It’s not really the basis of a healthy relationship.
By the end there’s the big rush to declare your feelings sequence, with a feel-good song and an attempt at a big romantic gesture but it feels conceited. There’s a 99% chance these two people will not live happily ever after, so the ending doesn’t feel like the triumph for love it’s framed as. While only being six years old, Playing It Cool is a rom com that feels far older with its attitude that men and women can’t just be friends, and some jokes that really fall flat due to their inappropriateness. 1/5.