Dennis Nolan (Dash Mihok) and his best friend Phil Fazzulo (Peter Facinelli) have found themselves working in a local Long Island pizzeria after graduating college. A stream of familiar faces from their past reinforces their humiliation over the fact that their lives have remained virtually unchanged. It finally reaches its most embarrassing peak when Phil can no longer dodge Deb Friedman (Jennifer Love Hewitt), a cloyingly sweet ex-girlfriend, while Kristen Barrett (Gina Philips), the ex-girlfriend Dennis couldn't hang on to, walks back into his life. In a five day span Dennis finds himself pondering his life and why it seems to have taken a turn down a road he never expected.