Craig Conover, known for his role on the reality television series *Southern Charm*, has garnered significant media attention for his romantic endeavors since the show premiered in 2013. His dating history includes notable relationships with cast members and other public figures, reflecting his quest for lasting love.
Conover’s early interactions on *Southern Charm* featured a flirtatious dynamic with co-star Kathryn Dennis during the show’s first season. Although the two had chemistry, Conover found himself in the friend zone before things could escalate. By season three, he began a serious relationship with Naomie Olindo, whom he met at the College of Charleston prior to joining the show. Their relationship progressed to cohabitation during season four, but they ultimately parted ways in 2017 after nearly three years together.
Following their breakup, Conover’s romantic life took a turn when he was linked to television personality Kristin Cavallari, which stirred up speculation about a possible love triangle involving co-star Austen Kroll. This was particularly highlighted in a January 2022 episode where Conover recounted a night spent with Cavallari, which he claimed Kroll was not pleased about. Despite the rumors, Cavallari denied any serious involvement, calling their connection a friendship that became exaggerated.
In September 2021, Conover publicly confirmed his relationship with *Summer House* star Paige DeSorbo. Their romance blossomed during season one of *Winter House*, and they made their relationship official while attending a wedding together. Over the next three years, the couple became known for their appearances across both shows, often supporting each other’s endeavors. However, in December 2024, DeSorbo announced their breakup, revealing that logistical challenges contributed to their decision. Sources indicated that Conover was ready to propose, but DeSorbo’s reluctance to move to Charleston created a rift.
Throughout his dating experiences, Conover has expressed a desire for a traditional family life. In a September 2023 interview with *Us Weekly*, he reflected on his relationship philosophy, stating, “I really only had rom-coms to base life off of. I thought you dated, there was a conflict, and you got engaged after you made up and you got married.” His aspiration for a “storybook life” includes settling down and starting a family, a sentiment he reiterated during a November 2023 episode of *Southern Charm*, where he mentioned wanting a “white picket fence.”
Conover’s dating journey continued with Natalie Hegnauer, whom he started dating in December 2020. Their relationship, which he described as significant, ended the following year. Despite the breakup, Conover maintained a positive outlook on love.
In March 2025, Conover hinted at a new relationship during a guest appearance on *Watch What Happens Live with Andy Cohen*. He expressed contentment and suggested that he was seeing someone special, later confirmed to be Natalie Buffett, who has prior relationships with NFL quarterback Dak Prescott and MLB pitcher Jack Flaherty. However, by June 2025, Conover announced he was once again single, acknowledging that he had not been ready for another relationship.
As Conover navigates the complexities of love and relationships, his experiences resonate with many who seek meaningful connections. His journey, marked by ups and downs, reflects a universal quest for lasting companionship.
