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Director: Justin Reardon

Writer: Chris Shafer

Top Billed: Chris Evans, Michelle Monaghan

What if I told you Shakespeare, and all the best writers were accused of being love hating sexual deviants? Thats precisely what Playing It Cool suggests.


Classic boy meets girl, boy falls in love, boy makes big monologuing speech, the end. For the most part that’s exactly what this quintessential Rom-com is going to provide. Following the cynical young screenplay writer (Chris Evans), who has a pessimistic view on the idea of love, and is ironically commissioned to write a romantic comedy  screenplay. Enter “Her” (Michelle Monaghan), a beautiful woman, interestingly open and up for anything. The two meet by chance at a charity gathering, where they playfully perform a “social experiment” and from there sparks seem to fly. That is until “He” (Evans) learns that this magical woman has a boyfriend affectionately referred to only as “Stuffy” (Ioan Gruffudd). Comedy ensues over the course of 80 plus minutes, where the cynicism is slowly replaced with sincerity for our feature couple to be.


Predictability is the name of the game for the “paint by numbers” rom-com Playing It Cool. Even in an attempt to play with the concept of the genre, it’s still mighty predictable. The attempted satire is regarding the idea that a loveless writer now has to write a screenplay about love. All the while the main character pokes fun at the stereotypical tropes that go into the rom-com genre. This would make for some great fun, if the movie itself didn’t actually proceed to accomplish all of the goofy shenanigans its main protagonist scoffs at.

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Playing It Cool fails to make the most of an exceptional cast.

The cast is a wide and steady group of talent. Evans and Monaghan are both quite serviceable, and the supporting cast ranges from the up and coming Aubrey Plaza to the more veteran Phillip Baker Hall. There are even smaller appearances from Anthony Mackie, as the agent, and Patrick Warburton, as an overzealous philanthropist. The cast is big and talented, and grossly under utilized. Most of the characters are pigeon-holed into the very stereotypes that are mocked in the early going. That being said, there is chemistry here. The two leads mesh quite well together and it makes their scenes, even with the foolish dialogue, memorable and enjoyable. There is solid rapport between Evans and his band of hipster writer pals, making for some mildly entertaining moments during their meeting of the mind segments, where they of course rally around their lovesick comrade.

Interestingly enough, there was an impressively somber and yet emotionally riveting back story that went almost completely unexplored. Evans character is a man with sincere abandonment issues due to his mother walking out on him as a small child. This concept became nothing more than anecdotal, electing only to use only as a plot device. In spite of its stereotypical storyline, some scenes by themselves do carry some emotional weight. There is a moment in which our “hero” drunkenly professes to “Her”, only to be knocked out by the boyfriend of “Her”. It is then we hear a line that resonated, at least with myself. He asks the question “do you hate me?” she achingly responds with “no, I don’t hate you. I nothing you.” Essentially this is the lovers equivalent to the adage “I’m not mad, I’m just disappointed.” This stingy banter is an example of what made this movie bearable.

The biggest highlight of the film for me, comes when our protagonists finally reads his gay best friends favorite book “Love in The Time of Cholera.” Summarizing the book in the scene discussing how it’s main characters tied a yellow ribbon to the boat to signify they have cholera (Skin disease) when they do not, simply so they may have there love untainted by the outside worlds influence. “He” then begs the question, in the boat of life who are the people that you would want on your boat with you? This scene is perfection, and it’s philosophy is probably the deepest Playing It Cool dared to go. It was the first truly beautiful moment the film had. It makes you ask yourself the question, on your boat of life who are the ones that you would want marooned with you?

Unfortunately for the viewer, This movie never gets past it’s shallow exterior. There were glimpses of depth, but they fade away quickly with the next predictably sarcastic situation. Only getting glimpses of sentiment from Evan’s character, including an emotional scene, where he re-reads the note his mother left himdownload (51) before abandoning him to a life of cynicism. Playing It Cool is a frustrating experience, because it truly could have been much more sincere without sacrificing humor. They could have explored these deep seeded emotional issues, but instead chose to just scratch the surface. The movie took the easy way out, to the dismay of it’s audience.


With an undeniably diverse and talented cast, solid emotional base, and good chemistry between the two leads, this movie had a real chance to provide a truly sentimental and thought provoking comedic love story. Instead it decides to do nothing original and just connects the dots from one scene to the next. There is a such thing as a heartwarming and humorous original Romantic comedy, Playing It Cool unfortunately isn’t that. While I would not say that this film is as low as a You’ve Got Mail, it’s also nowhere near as high as a When Harry Met Sally. Playing it cool falls unremarkably in the middle of it all. Even the star power of this film cannot save it from it’s utterly ridiculous and predictable plot devices. I will give Playing It Cool a 2/5. It’s a likable movie with likable characters, but it’s just too simple and too safe for it’s own good.

Check it out on VOD if you’re interested!

2/5 Do Better Bro