Playing it Cool is a fresh, quirky and weirdly relatable story about Me (Chris Evans), a young screenwriter disillusioned by love. He meets a breathtaking young woman, Her (Michelle Monaghan), at a charity dinner by pretending to be a philanthropist. Only one problem...she's engaged. With his agent (Anthony Mackie) chasing him for a screenplay about love and against the better advice of his best friend Scott (Topher Grace), 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.