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.

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.