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there are two movies that almost run parallel with each other with obvious identical similarity, this 'playing it cool' is almost like the other most pathetically boring 'lovesick'. i really don't know if these screenplay writers are just roommates renting the same apartment together, or they are just renters next to each other, or on the same floor. but these two screenplays are just as bored as each other, and the difference is so little, only the storyline shuffled a little bit. but obviously, the budget of 'playing it cool' is several times bigger than the 'lovesick', less roles, compensated by mucho kids players instead. but both so-called 'romantic comedy' turned out to be so boring, so exaggerated, so pretentious, and so contrite, and both should never be approved to be produced. the investors of these two movies should have give their money to the charities, at least the money won't be wasted like this.

The writing is obnoxious in ways to which the creative team seems to be oblivious. Finding out the protagonist is an LA screenwriter is a RED FLAG -- telling us that (chances are) the writer lacks worldly experience (outside of showbiz in LA) and lacks imagination (or even just research into other fields).

The writer (Evans) and his pals live privileged lives (affluence without real work) in a fantasyland version of Venice Beach, Malibu, etc. The story takes all that for granted (like it's just air, natural and common for all), then expects us to care about the characters and their silly activity. That oblivious presumption, permeating the whole movie, is obnoxious and repellent. So after maybe 15 minutes I can see that this movie is a waste of time.

Life goes by too fast to watch movies like this. I stopped watching.

All of the actors were appealing, and Topher Grace displays impressive talent and craft, being entertaining & amusing in the subtle details of his performance. I really hope he gets lots of great material for years to come, but it looks unlikely, given this movie was made six years ago, and TG's career seems to be rather quiet and low profile for the past several years.

Evans and Monaghan have really good chemistry on screen. I am surprised at the quality of Evan's acting chops. I think the guy is pretty talented. He's able to pull off drama and comedy well.

There have been many great rom-coms over the last 10 years, but it's a largely dead genre, at least when it comes to movies that make it into theaters. 'Playing it Cool' is just about as cliche as they come with this genre, even though the film tries its darndest to do the opposite. Chris Evans and Michelle Monaghan play the two central characters, both of which I love in just about anything, but they are given next to nothing with this script. It's also the only film Justin Reardon has ever directed, which should tell you something about how this film was received within the industry. Perhaps the worst part is that it feels long at 90 minutes. That's when you know something is wrong with your pacing, writing, and direction. 'Playing it Cool' contains a few moments of genuine charm, purely from its actors, only to be outdone by the next extremely cliche plot point.

5.4/10

Rom-Coms are not the easiest to make. If you try to make a real good one that is. But even the "bad" ones make their money back mostly. And I wouldn't categorize this as a bad one. Does it have some misplaced dialog and some clichés in it? Yes, though it's not the first one to do so and its lead actors are charming enough for you to not care too much about that.

While the inevitable outcome is predictable, there may be a few obstacles along the way that are kind of refreshing to see. And while our main protagonist could easily slip into unlikeable territory, Chris Evans is there to save him from that fate. No pun intended, for a decent effort. Nothing more, but certainly nothing less either