David Collins (Jerry O'Connell) is a commmitment-shy Los Angeles yuppie whose girlfriend of many years, advertising executive Sarah (Bridgette Wilson-Sampras), gives him an ultimatum: commit or get out. David has two months to decide if he wants to stay with Sarah as she leaves town for a job in New York. Following the advice from his more outgoing friends, David hits the dating scene as he tries to find his one and only soul mate, a mysterious woman he sees again and again, but always gets away before he can talk to her.