Playing It Cool (2014)

In the kaleidoscopic world of "Playing It Cool," we journey alongside a screenwriter, a little worn and jaded from the harsh realities of love, grappling with the task of penning a romantic script. His skepticism, a scar from a childhood abandonment by his mother, is his constant companion, compelling him to sabotage his own relationships. Desperate to breathe life into his sterile script, he turns to his friends for inspiration, but their experiences fall short of igniting the spark he needs. At a charity dinner, under the guise of a philanthropist, he encounters a woman of such mesmerizing beauty that it stirs his dormant heart. The only hitch? She's already engaged. Undeterred by this, he enters into a friendship with her, allowing him to keep her in his life, even if not in the way he desires. As the plot unfolds, we see our protagonist evolve into a modern-day Walter Mitty, resorting to the potent power of imagination and whimsical vignettes to win her over. Like a seasoned chess player, he's always strategizing, planning his next move, willing to stop at nothing to capture the queen - her heart. "Playing It Cool" is a vibrant exploration of love and longing, where reality and fantasy intertwine, painting a vivid canvas of the timeless quest for love.

Playing It Cool is a comedy movie featuring Chris Evans.

Playing It Cool is currently streaming for free (ad-supported) on VUDU Free and YouTube Free and it's also available on Starz, Starz Amazon Channel, Starz Apple TV Channel and Starz Roku Premium Channel.

It is also possible to buy Playing It Cool on Amazon Video and Vudu.