Craig Conover, known for his role on Bravo’s reality series *Southern Charm*, has had a love life that has captivated fans since the show’s premiere in 2013. His relationships, both public and private, have often made headlines, showcasing his journey through romance and heartache.
Conover’s dating history began with a flirtation with co-star Kathryn Dennis in the show’s inaugural season. While the chemistry was evident, Conover found himself in the friend zone before their relationship could evolve. By season three, Conover was in a serious relationship with Naomie Olindo. The couple’s dynamic featured prominently on the show, with their cohabitation and struggles being a focal point. However, their romance ended in 2017, reportedly due to conflicts, including Olindo’s critical remarks about Conover’s passion for sewing.
Following their breakup, Conover’s romantic escapades included an alleged encounter with television personality Kristin Cavallari. This rumor gained traction after a love triangle was hinted at during a *Southern Charm* episode featuring Conover and his then-girlfriend, DeSorbo. Cavallari later downplayed the situation, claiming it was merely a drunken kiss.
Conover found love again with Paige DeSorbo, a star from *Summer House*. Their romance blossomed while filming *Winter House*, and they officially went public in September 2021. The couple frequently supported each other’s careers, making guest appearances on each other’s shows. However, by December 2024, DeSorbo announced their split, citing logistical challenges stemming from their long-distance relationship. Insider reports suggested that Conover was ready to propose, but DeSorbo hesitated, ultimately leading to their breakup.
Despite the ups and downs, Conover remains optimistic about love. During an interview with *Us Weekly* in September 2023, he shared his perspective on romance, stating, “I really only had rom-coms to base life off of,” implying that he views relationships through an idealistic lens. He expressed a desire for a “storybook life,” complete with the traditional elements of marriage and family.
Conover’s dating journey took another turn when he hinted at a new relationship with Natalie Buffett in March 2025. He described feeling happy and content, although that relationship was brief, as he confirmed being single again by June 2025.
With each chapter of his romantic life, Conover remains committed to finding lasting love. His candid reflections on dating and relationships resonate with many as he continues to navigate the complexities of love while in the public eye.
As *Southern Charm* progresses, viewers can anticipate more developments in Conover’s life, especially as he openly expresses his aspirations for a family and a stable future. His journey serves as a reminder that even in the glitzy world of reality television, the pursuit of genuine connection remains a universal experience.
