Shep's journey to find love comes closer to an end. Shep looks to his roots for guidance. Peyton fits in perfectly at a getaway to Shep's family farm; and Priscila proves to be the perfect partner at an overnight at his mountain house. Feeling conflicted, a talk with Mom reminds Shep to follow his heart.
Shep says goodbye to his road trip of love and invites a few ladies back to Charleston. Cameron begins her own interrogation of the ladies. After some speed dating and sightseeing, a beach party turns salty when Shep tries to juggle five women at once. Later, an unexpected guest knocks the wind out of the already full house.
Shep searches for someone to date in the Lone Star State. Shep goes on an unusual double date; uses his escape tactics to reach a beautiful brunette; and a health scare throws his New York state of mind back into reality.
Shep's search for love takes him cross-country. He finds puppy love with a dog groomer, declares poetic justice on an unwilling guest, and makes a faux pas when Landon crashes his date. Things improve in Dallas when he falls for an edgy beauty queen.