Author Eric Scheaffer goes on a journey to look for love, from Portland, Maine to Portland, Oregon. Eric starts off in New York City, on a date with dominatrix, then goes to Los Angeles and meets up with a struggling actress.

Eric meets a musician while he attends a spa and tries to set up a date with her; Eric then meets up with family members at one of his book signings.

Eric starts to think that the drivers of semi's are trying to run him off of the highway; later he tries to talk one of his fans to come and meet him for a date

While in Salt Lake City, Eric tries to see if he can pick-up women that are Mormon; later he interviews a woman is a born-again Christian.