Craig Conover, a prominent figure from the reality television series Southern Charm, has garnered significant attention for his evolving romantic life since the show’s debut in 2013. His relationships, both on and off-screen, have captivated audiences, showcasing a blend of public romances and personal aspirations for love and family.
Conover’s first notable relationship was with his Southern Charm co-star, Kathryn Dennis. While they shared a flirtatious dynamic in the first season, he found himself friend-zoned before things could escalate. By the third season, he was in a committed relationship with Naomie Olindo. Their romance progressed quickly, as they moved in together during season four. However, the couple’s relationship faced challenges, leading to their split in the fall of 2017 after nearly three years together.
Following his breakup with Olindo, Conover’s love life continued to intrigue fans. Rumors circulated regarding a brief encounter with television personality Kristin Cavallari, but he later began dating Paige DeSorbo, a star from the reality series Summer House. The pair initially connected during the first season of Winter House and went public with their relationship in September 2021 at a wedding.
Throughout their three-year relationship, Conover and DeSorbo frequently appeared on each other’s shows, highlighting their commitment to one another. However, their dynamic shifted, and DeSorbo announced their breakup in December 2024, revealing that the decision stemmed from geographical challenges. Conover had been eager to settle down and even had plans to propose, but differing life goals proved to be a significant hurdle.
In a candid reflection on his dating philosophy, Conover shared with Us Weekly in September 2023, “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 yearning for a traditional family life is evident, as he expressed a desire for “that storybook life” and a “white picket fence” during a November episode of Southern Charm.
Exploring Conover’s Notable Relationships
Conover’s dating history is marked by a series of noteworthy relationships that have shaped his perspective on love. His time with Olindo was significant, as they met while attending the College of Charleston and quickly became a fan-favorite couple. The tension in their relationship, particularly regarding Conover’s passion for sewing, ultimately contributed to their split.
In May 2022, DeSorbo hinted that Conover and Olindo had a casual encounter during the early stages of her own relationship with Conover. Olindo later clarified that it was not a rekindling of their romance but rather a fleeting moment of comfort amidst recent breakups. She confirmed her own engagement to Billy Haire in December 2025.
After his relationship with Olindo, Conover briefly dated Natalie Hegnauer, whom he met in January 2020. Their connection was highlighted during Conover’s Southern Charm debut, where he expressed strong feelings for Hegnauer. However, their relationship ended within a year, with Conover announcing his single status in May 2021.
Rumors of a love triangle involving Cavallari, Conover, and his co-star Austen Kroll emerged in July 2021. While Cavallari initially denied any romantic involvement, she later acknowledged a brief kiss with Conover during a September 2023 appearance on Watch What Happens Live with Andy Cohen.
Conover’s most recent relationship was with Natalie Buffett, which he hinted at during a March 2025 interview. Although he expressed happiness, the relationship was short-lived, and he confirmed his single status again in June 2025. Reflecting on his experiences, Conover stated, “I just wasn’t ready to date but I didn’t know that. There’s no guidebook for this.”
As Conover navigates the complexities of love, his story remains relatable to many. His journey illustrates the challenges of modern relationships, particularly those played out in the public eye. With aspirations for a future family and the determination to find lasting love, Conover continues to capture the attention of viewers and fans alike.
