Kevin has everything going for him, but his lifelong lack of confidence keeps him from recognizing love and happiness -- even if it's sitting next to him. When Kevin meets the girl of his dreams, Abbey, on Chicago's L train, they connect immediately but he lets this golden opportunity slip away by not having the courage to ask her for her name and number. Unable to find her, or forget her, Kevin and his buddies launch a massive campaign to locate Abbey.

Steve Baker is a night watchman who's in his early 20's but his life is already getting away from him. His band is falling apart, he owes a ton of money for drugs, and he's in love with his best friend's girl. When Marty Lyons comes along and ropes Steve into a criminal world of oddballs, misfits, and lost souls that are as dirty as the Charles River, Steve wonders if this is a change for the better or if he's about to make the worst decision of his life.