"Playing It Cool" is the story of ME (Chris Evans), a young man disillusioned by love, who meets a breathtaking young woman, HER (Michelle Monaghan), at a charity dinner by pretending to be a philanthropist.

Only one problem: she’s engaged. Yet, he engages into a platonic relationship to be able to keep seeing her. Like a young ‘Walter Mitty’ using the power of imagination and wild vignettes, ME will stop at nothing to conquer HER heart.The movie directed by Justin Reardon also stars Topher Grace, Ioan Gruffudd, Aubrey Plaza, Martin Starr, Luke Wilson, Philip Baker Hall, and Anthony Mackie.

The movie will be available in theatres on May 8th, 2015. Enjoy the trailer below.