The ultimate New York City playboy Jack Frost (Jason Behr) is shattered when he discovers his one true love Carolina (Monet Mazur) is about to marry another man. Still haunted by his mother's suicide, Jack spirals into a self-destructive cycle of whiskey and reckless behaviour, while his best friends Ozzy (Krysten Ritter) and Scotch (Mike Landry) try to jar him back to reality. Strangely enough, it's Jack's eleven year-old neighbour, Sophie (India Ennenga), who helps the drowning urbanite shake off the nostalgia and excess that threaten to consume him.