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Nicely directed , the cast is Hilarious from Chris Evans, Aubrey Plaza to Topher Grace .. started with a well put Hilarious bits , tuned down then the romance peaked which just the definition of romance comedy.

The scenario escalated gently and understandably , the "Narrator" explained exactly how things work on a romance comedy then the movie just stared showing what has been explained , also the flashbacks for each story any of the guys tell was spot on.

the only thing i'v noticed , which not just here in this movie but also in the recent ones is that the writers generally trying to spread the idea of "it's okay to cheat on your partner if you're trying to finding love" !!! i don't know but it feels kinda wrong to me, yet it wouldn't serve the purpose of the movie here or the concatenation of the event..but still ;)

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

A Hollywood screenwriter (Chris Evans) is assigned to write a rom-com. The problem is that he wants to write action and has never been in love. Being abandoned by his mother at an early age has left him commitment phobic. His group of writer friends include Mallory (Aubrey Plaza), Lyle (Martin Starr), Samson (Luke Wilson), and Scott (Topher Grace). It's love at first sight when he meets a woman (Michelle Monaghan) at a charity event except she already has a boyfriend.

Writers Chris Shafer and Paul Vicknair also wrote Chris Evans' directorial debut. So it's not a shock to see Evans involved in this one and he probably brought along all these friends of his. The premise has limited bite and even less originality. There's nothing new here. Plaza does have great fun playing the wackiest of the group. The romantic couple is saved by Evans' inherit personal charms. I love Monaghan but she's not better than peak Meg Ryan. There's even a diner scene but this movie is nowhere near the icon. Other problems include the use of the lead characters in the imagined stories. They are obviously trying hard to be magically charming but all they do is to leave the movie in neutral. They lack anything interesting to justify taking a break from the plot such as there is one. Generally, this is a bland rom-com with one or two funny side characters.

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.