‘Southern Charm’ Star Craig Conover’s Dating History: Naomie Olindo, Paige DeSorbo and More

DeSorbo and Conover got close during season 1 of Winter House but didn’t go public with their relationship until September 2021 while attending Amanda Batula and Kyle Cooke’s wedding. Throughout their three-year relationship, DeSorbo made cameos on Southern Charm and Conover returned the favor, appearing on Summer House.

DeSorbo announced in December 2024 that she and Conover called it quits, later revealing she broke up with him over Thanksgiving. DeSorbo remained in New York and Conover in Charleston, South Carolina, throughout their romance, which a source exclusively told Us played a part in their split.

“Craig was ready for the next steps and had plans to propose to Paige. He was really pushing for the next steps and wanted to settle down with her,” the insider told Us in December 2024, claiming, “Paige does not want to move to Charleston, and logistically it was never going to work out long term.”

The breakup was detailed during the Southern Charm season 10 finale, which aired in March 2025. At the time, Conover said he bought an engagement ring, but DeSorbo told him to “hold off” on a proposal, which never came. DeSorbo’s side of the story will be covered on the Summer House season 9 finale, airing later in 2025.