‘Southern Charm’ Cast’s Dating History: Inside Shep Rose, Craig Conover and More Stars’ Love Lives

Austen briefly dated costar Chelsea during season 4 of Southern Charm in 2017 before things fizzled out. Their romance played out a little bit in season 5 when he was dating the stylist's friend Victoria, who continually questioned his loyalty amid Austen's friendship with Chelsea. The Kings Calling Brewing founder found love again with Madison, but the pair's rocky relationship came to an end after two years, with Madison confirming to Us in December 2020 that they were over. Following his split from Madison, Austen sparked romance speculation with Cavallari, after the pair partied together in late 2020. "She came to town with her friend Justin and the four of us [with Craig] had dinner," Kroll told Us in November 2020 of their friendship. "We've all been in contact ever since. We're in this, like, big old group chat, and the group chat is active. We had a blast with them." The duo were again spotted with their mutual friends in June 2021 when the Laguna Beach alum came to South Carolina for a visit, but have denied dating rumors in the past. Austen briefly romanced Winter House costar Ciara Miller in early 2021 while filming the spinoff series in Vermont. The duo were flirty during Austen's visit to the Hamptons that summer, which played out on season 6 of Summer House. The North Carolina native, however, got himself into trouble when he made out with longtime friend Linsdsay Hubbard while staying at the group's house. In May 2022, Austen confirmed to Us that he was dating Olivia Flowers, who joined the cast of Southern Charm for season 8.Olivia revealed during the season 8 reunion, which aired in October 2022, that she and Austen had called it quits. In early 2023, Austen made headlines when rumors swirled that he and Shep's ex-girlfriend Taylor had hooked up ahead of season 9 of the series. The twosome denied the allegations at first, but Austen later confessed — during an October 2023 episode of the show — to Shep that he and Taylor had "kissed" and nothing more. Austen and girlfriend Audrey Pratt made their Instagram debut in February 2024 when Austen shared photos of the pair on a group trip to Mexico.