follows Charleston's most eligible and loveable singleton, Shep Rose, as he ventures to various cities across the country in the hopes of finding true love and a committed relationship. Shep is a complicated bachelor, and the right match will have to effortlessly fit into his particular lifestyle which ranges from black tie galas to surfing with him in Costa Rica. As Shep leaves Charleston to look for "the one," he calls upon his friends in various cities from New York to LA to help set him up with women in hopes that they are a perfect match.