Whether it's his Bravo connections or more under the radar relationships, Craig Conover's love life has been making headlines since Southern Charm's 2013 premiere. Conover had a flirty relationship with costar Kathryn Dennis during season 1 but he was friend-zoned before it turned romantic. By season 3, however, he had a full-fledged girlfriend in Naomie Olindo. Following their 2017 split, Conover raised eyebrows for an alleged hookup with Kristin Cavallari before dating Summer House's Paige DeSorbo for three years.