In the nerve-wrackingly unfunny Playing It Cool, Chris Evans stars as a nameless hack screenwriter—listed in the credits as “Narrator”—tasked with penning a stars-attached romantic comedy on a tight deadline. Because Justin Reardon’s film believes in both showing and telling with equal conviction, Narrator articulates his fundamental predicament though arch voiceover: He doesn’t believe in love. As depicted in a hurried montage, the supermodel-grade women in his love life have been mere flings, falling for him to no reciprocation. But that changes after a chance encounter with an also-unnamed woman (Michelle Monaghan), and soon Narrator unconvincingly reflects unconvincingly: “My whole life, I’ve felt guilty after sex. Guilty for everything I’d said and done to get there. But the thing I learned is, when you actually care about the person, you don’t feel guilty.”
Monaghan and Evans manage to be individually disarming despite their parts, with scant chemistry to speak of—one of many instances where the film’s considerable star power is squandered. Anthony Mackie features as Narrator’s sex-and-money crazed agent Bryan (Xeroxing the genre archetype of the co-worker/best friend, duly reiterating the movie’s trope-laden turns back to its protagonist), while Aubrey Plaza and Luke Wilson feature as his drinking buddies/colleagues. It will surprise no one that Plaza’s character has been enamored with Evans’s since they first met—a confession made by her character in a moment of weakness, and smoothed out in an impossibly pat and uncomplicated resolution. Soon after a roughing-up from Monaghan’s fiancée (Ioan Gruffudd) and the death of his grandfather (Philip Baker Hall), Narrator is taught a battery of forcible life lessons, making him realize he and Monaghan belong together while he discovers the mystery grist for his writing assignment.
As characters endlessly digress on the differences between rom-coms and real life, Playing It Cool evinces a schizophrenic relationship with its own inside-baseball cynicism: Narrator is drawn as a shame-ridden womanizer, but none of his behavior is shown to directly hurt anyone other than his best friend, Scott (Topher Grace). Scott disowns Narrator after he fails to read Scott’s well-loved copy of Love in the Time of Cholera, which Narrator eventually makes short work of in a single sitting, extracting from the book only the most mawkish catchphrases in true Hollywood form. Further “laughs” are generated by the Narrator’s repartee with Bryan, who stretches a flailing moan of endorsement for Malaysian sex tourism so far out, it’s almost as though Reardon includes Evans’s pained reaction as metatextual embarrassment. The star’s nudge-nudge geniality has been a boon to his Captain America character, but here it’s in service of an antihero who seems aware of his own douchebaggery from the film’s kickoff, and this is the world its characters inhabit: They’re starring in a clichéd film both about and composed of clichés, and they’re loving it.