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.
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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.
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