Premise: A screenwriter who doesn't believe in love falls in love with an unavailable woman.
This is the kind of bad movie that plays into enough of my personal weaknesses that the taste centers in my brain act like it's a good movie. That's not even the same as a guilty pleasure. It's akin to using the ingredients of my favorite food to make something I don't like. There we go. Playing It Cool is making a burrito that's 50% sour cream and almost no rice or queso. In the right light, Playing It Cool looks like What If? and Alex & Emma: two RomComs I refuse to feel shame for enjoying. I like RomComs and movies that play with narrative structure. The reason I watched it in the first place is because this is one of those "OMG, this cast!" Movies that I've mentioned before. There are simply too many actors in this I like to ignore it: Chris Evans, Michelle Monaghan, Topher Grace, Aubrey Plaza, Luke Wilson, Martin Starr, Anthony Mackie (an MCU favor, no doubt), Philip Baker Hall, Patrick Warburton. It even has Kyle Mooney in an "Other Guy" role. For a movie that barely got a release on VOD, that's so many familiar faces.
I enjoy seeing enough of these actors on screen that individual scenes were often enjoyable just for who was bouncing lines off each other. This movie reminds me that Michelle Monaghan needs more to do. She works steadily. I can't think of something she's been bad in. How has so much of her career been wife/girlfriend roles? Does she have some indie movies I need to check out?
...I'm having a hard time figuring out how to describe why I didn't care for this movie. Because, again, it has all the pieces of a movie I would like. Sadly, much of it does tie back to Chris Evans. He has two proven modes that work for him: jackass and Captain America. He's not great at playing thinkers or reflective-types. His character in Playing It Cool needs someone who is constantly in his own head to the point of being accidentally inconsiderate. Put bluntly, if Evans is being inconsiderate, he knows it. It never looks like an accident with him. And his life doesn't really feel like it's a mess. He's apparently a very successful screenwriter and hardly ever has to work. He's able to do stuff like drop loads of money to attend charity events. The movie doesn't seem to realize how much the audience isn't rooting for him. When he and Monaghan finally hook up, I wasn't really rooting for it. Poor Ioan Gruffudd doesn't even get enough screen time to be an asshole. He's just an unassuming guy who is being cheated on.
This movie is a little too full of RomCom touches. Evans plays his heart as a second character standing at a distance. Topher Grace randomly leaves his favorite book - Love in the Time of Cholera - around for people to find. Monaghan buys a card for herself from her father every year because he died around that time. Evans chases heart statues around San Francisco. The movie is a too aware that it's in a RomCom. Oh yeah, Aubrey Plaza secretly being in love with Evans. Evans' grandfather dying in the middle of all this. His lie about charity sort of blowing up in his face. Frankly, I didn't even think Monaghan believed he was that charitable before Warburton exposed him.
It's frustrating, because this movie is only a few tweaks and calibrations away from me eating it up. I would've happily traded of some cleverness for sincerity.
Side Thought: Monaghan is 5-years older than Evans. I was going to use that as a jumping off point to note a trend of more Romance movies lately having women who are older than the men. Then I realized the first three examples I had were all Henry Golding movies (Crazy Rich Asians, Last Christmas, A Simple Favor). So, maybe it's not a trend as much as a Henry Golding thing.
Verdict: Weakly Don't Recommend
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