Shep Rose has a dream of being married with two kids by the time he turns 40. The most famous bachelor in Charleston, S.C., is cutting it pretty close. He hasn't found his free-spirited, smart and outdoorsy girl in the bars of his hometown. Instead, he takes his search on the road to visit friends who work to set him up on blind dates with friends they think would fit well with him. Shep is searching for "the one" who can fit into his lifestyle. He visits popular locations such as Los Angeles, Dallas, Austin, and New York City.