After a divorce, Will lives in Florida with his dog Charley. His parents, Shaina and Philip (plus 2 stepparents), along with the town of Milledgeville, are on a mission to help him find love again.

Leighann is a wedding planner who has not found her groom yet. Returning to her hometown to help plan her sister's wedding, she discovers her family and town have arranged three blind dates for her with locals looking for love.

Larry Jr.'s career-driven life leaves little time for love. Back in his hometown, he is set up on 3 dates, where he and his family hope to find someone with shared values and a deeper connection than the NYC party scene offers.