Roswell star Jason Behr assumes the role of a New York City playboy who sinks into a deep depression after learning that his childhood love is engaged to another man. Still haunted by his mother's recent suicide, professional charmer Jack Frost (Behr) is shattered to discover that his one true love is about to take the plunge with another man. As Jack begins spiraling into a self-destructive cycle of whisky and reckless behavior, his best friends Ozzy, Scotch, and Kate struggle to find a means of jarring their depressed pal back to reality. Strangely enough, it isn't Jack's grown-up friends who offer him the most useful relationship advice, but his eleven year-old neighbor Sophie, whose unusually wise and thoughtful words have a special way of helping the self-absorbed urbanite shake off the nostalgia and excess that may ultimately consume him.