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There's lots to like here. The two leads are good enough, The gang of friends offer a little light relief and the script is quite funny in parts.

However, it lacks that 'spark' that should push it over the top and join the other storied examples of the genre like, 'When Harry Met Sally,' or 'Sleepless In Seattle'.

The problem is that it only tells the story from side of the relationship. It tells us nothing about the girl, and why, strangely, that she is in a relationship herself.

The audience as @ result feel no great empathy toward either of our lovers. One is a cheater and the other doesn't believe in love.

Watchable but nothing more.

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

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.

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

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 ;)