On the Line (2001)

"Have you ever met the perfect girl... and let her get away?"

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.