Newport Beach Film Festival 2008

Jack Frost’s carefree bachelorhood in New York is rocked by the news that his oldest girlfriend, Carolina, whom he has loved since childhood is engaged. The news throws him into an existential crisis in which he is forced to really look at his life. At age thirty-five, stuck between a vision of himself from childhood and his failure to grow up, Jack sinks into depression. With the fumbling help of his best friend Scotch Evans, a nightlife correspondent for a local news station; a friendship with Ozzy, a loving but troubled young heroin addict; the prodding of Kate, a reporter writing about playboys in Manhattan; and his eleven-year-old neighbor, Sophie, Jack struggles to overcome doubt and heartbreak and find new meaning in his life.