Finding “the one” is a complex quest with no sure fire directives. For most people it’s a matter of trial and error, and even then it may not live up to expectations or be everything you pictured. Unfortunately love is not an exact science, though learning from those experiences is part of the journey. In Playing it Cool, a man whose shunned love most of his life is surprised to find his ideal match is unavailable.
The Narrator (Chris Evans) is a screenwriter contracted to develop a rom com in spite of his lack of experience with being in love. Conversely his best friend, Scott (Topher Grace), is a hopeless romantic who views the world through rose-coloured glasses. Procrastinating through writer’s block, the Narrator goes to a charity event where he meets Her (Michelle Monaghan). She flawlessly matches his wit and sense of humour, encompassing everything he could want in a woman — except that she’s in a serious relationship with another man.
Possibly in an attempt to universalize the couple, neither character is given a name at any point in the film. He is dubbed “Narrator” in the credits and she is appointed the title, “Her.” It’s possible the viewer can go the whole film without even realizing these key figures are nameless, though the Narrator’s friends all have names and Her boyfriend is simply known as “Stuffy.”
The irony of a man commissioned to write a rom com who finds himself living one out is not lost on the Narrator. He repeatedly refers to his actions as cliché and acknowledges when he’s playing into the genre’s trappings. But just because the film is self-aware, that doesn’t mean it’s any less conventional. The Narrator is still the stereotypical guy who fears intimacy because of some childhood trauma inflicted by his mother. She is the traditional total package that doesn’t require a lot of imagination to understand why he’s so taken with her. The Narrator’s desire to eventually woo Her away from her boyfriend by being “just friends” and demonstrating how much better of a match they are is both stale and somewhat offensive. The F Word (a.k.a. What If) did a wonderful job telling a very similar story but without the deviousness.
One of the elements meant to set this narrative apart from other traditional rom coms is the interludes that feature Evans’ and Monaghan’s characters recreating a story being related by another character, whether it be the plot of a book, movie, story idea or personal experience. Imagining himself in other people’s romances is apparently how the Narrator connected to love prior to his encounter with Her. While these performances-within-a-performance are amusing, they do seem to get a little excessive by the end. Although imaginary repeat appearances by Matthew Morrison and Ashley Tisdale as frustrated actors waiting for their script are as odd as they are amusing.
Evans and Monaghan are perfectly charming, and play together very well. He is a little neurotic, but is normalized by his writer friends who view the world in the same way. She is a model female lead though some of her character’s actions are questionable, appearing more integral to moving the plot in a certain direction than being true to the situation. In the end this is an enjoyable self-reflective rom com that focuses a bit too much on being the former instead of the latter.