Justin Reardon’s romantic comedy, Playing It Cool, is equal parts whimsy, humor and heart. Chris Evans stars as the film’s nameless narrator, a screenwriter who just landed a job writing what could be the next romantic comedy box office hit. There's just one problem: he doesn’t believe in love.
Instead of putting words to paper our narrator nurses his writer's block the way any good writer does, by wasting time with his circle of misfit writer friends; they offer lots of laughs if not much in the way of meaningful advice. The one exception is do-gooder and hopeless romantic, Scott (Topher Grace), whose favorite pastime is leaving behind signed copies of Love in the Time of Cholera for strangers to happen upon while visiting their favorite coffee shop or restaurant. So it's fitting that it is while attending a charity function with Scott that Evans' character meets HER - he’s a cynic, she’s a realist, but neither one of them is prepared for what happens next.
Reardon utilizes voiceover narration, dream-like sequences, animation and other fantastical elements to invite the audience to get inside the head of this everyman protagonist as he experiences the ups and downs of falling in love.