Playing It Cool

Here’s one of Chris Evans’ first voiceover lines in Playing it Cool: “See, I’ve been hired to write this romantic comedy screenplay….” If your brain isn’t inserting “The problem is I’ve never actually…been in love” into the pregnant pause before Evans himself says it, I don’t even know you anymore.
Evans’ character has no name; his eventual paramour (Michelle Monaghan), who for most of the movie is engaged, also lacks a name. An hour and a half of nonsensical Love in the Time of Cholera references later, they still don’t have names, but they are in love—just like in Ghost, which the movie also references. Because this is a film about a writer, see, and those are always the best!
There are two good things about this film. The first is that, admittedly, I didn’t notice that Evans’ and Monaghan’s characters don’t have names the first time I watched it, which means the conceit is not quite as annoying as it sounds. The second is that the film employs a bunch of actors I enjoy, like Aubrey Plaza, Luke Wilson and Martin Starr. And the actors do seem like they’re having a good time with each other. Unfortunately, that’s mostly in the sense of “Can we finish this take already so we can get back to the actually funny conversation we were having between takes?”
The rest of Playing it Cool is fairly typical for the kind of film it is. Fratty enough to be offensive, but not fratty enough for you to believe in the conviction of the writer’s will to offend, which makes you wonder why they bothered crafting lines like “this cigarette is like an elephant’s dick” in the first place. The film’s meet-cute is a mostly eye-rolling conversation about the objectification of women that begins when Monaghan overhears Evans complaining that all of the women at a party are ugly; they immediately fall in love because they have crackling chemistry while sarcastically discussing women’s rights, I guess? I think that’s the point, but I only know they have crackling chemistry because Evans’ voiceover narration tells us they do and also because they hold hands briefly and there are CGI sparks.