In the vein of Amelié and (500) Days Of Summer, Playing It Cool is a fresh, quirky, and weirdly relatable story about Me (Chris Evans, Captain America: The Winter Soldier), a young screenwriter disillusioned by love. He meets a breathtaking young woman, Her (Michelle Monaghan, Source Code), at a charity dinner by pretending to be a philanthropist. Only one problem... she’s engaged. With his agent (Anthony Mackie, Pain and Gain) chasing him for a screenplay about love , and against the better advice of his best friend Scott (Topher Grace, That 70s Show), our young hero enters into a platonic relationship to be able to keep seeing Her. Playing It Cool is a story of love and quarter-life crisis amidst figuring out who you are and what your destiny holds.