“I know our show for a while is [synonymous with] Peter Pan syndrome. But now that’s just not the case anymore,” he said. “I think it’s more the dynamic between the three oldest friends on the show, guy wise, is what’s interesting this year, ’cause you have Austen really accepting this new way of life where he seems so much lighter and happier. You have Shep, [who is] really torn on what he wants and what he thinks he wants. And then you have me, where a guy gives a couple of teases of settling down. It hasn’t happened yet, so you get to see a bunch of single guys having fun again.”
Below, learn more about Craig’s past and present relationship history.Â
Is Craig Conover dating anyone?
Craig is currently single as of October 2026. He appeared on the We Met at Acme podcast on Oct. 11, where he elaborated on his current status. “I’m single and really only dating with intent,” he said during the episode. “I think I’m just in that state of my life. I think you get addicted to peace, and I’ve found peace.”
Craig Conover and Naomie Olindo’s past relationship and where they stand today
Craig dated Naomie Olindo from 2015 to 2017, during the early seasons of Southern Charm. He cited the demise of their relationship at the time to Bravo Insider to being “too different” of people.
 But, Craig and Naomie are close today. “We’re friends now, which is great,” Craig said on the We Met at Acme podcast. “I’m glad that we were able to become friends and her husband [Billy Haire] is super nice and has flown that New York flight with me a couple of times because he goes back and forth from Charleston and New York.”
On the October 13, 2026 episode of Watch What Happens Live With Andy Cohen, Craig shared that he had congratulated Naomie on her recent marriage. “Naomie and I are friends now,” he reiterated. “Charleston’s a small world.”Â
Craig Conover and Natalie Hegnauer’s past relationship
Craig openly dated Natalie Hegnauer during Southern Charm Season 7. The couple continued to date during the filming of Winter House Season 1, where he met his ex-girlfriend and Summer House alum Paige DeSorbo.
RELATED: Craig Conover Reveals Major Life Updates After Season 11: “Dreams Loading”
Craig Conover and Paige DeSorbo’s past relationship and where they stand today
Craig was in a relationship with Paige, who he started dating in May 2021 after his breakup with Natalie. The couple did the majority of their relationship long-distance with Paige living in New York while Craig continued living in Charleston. But, they were very serious about their relationship, attending weddings and traveling the world together.Â
However, Paige announced in December 2024 that she and Craig had broken up, admitting that it was the “right” decision for the both of them. In the months after their breakup, Craig shared that he had bought an engagement ring for his ex, and shared more details about their breakup during Part 1 of the Southern Charm Season 10 reunion. “She was like, ‘I am probably making the worst decision of my life, but I need to go find myself,'” he recalled. “I will say that when we were together in private is what I based our relationship off of. And there weren’t signs.”
On WWHL‘s October 13, 2026 episode, Craig praised Paige’s recent business success. “She’s doing great,” he said. “It’s a great example of hard work pays off. I hear she got a huge deal and everyone should start to take accountability of their own lives of being like, ‘If I put the work in, it has a chance of working out.'”
Craig Conover’s romance with Natalie Buffett
Craig briefly dated influencer Natalie Buffett following his breakup with Paige. He explained during Southern Charm Season 11, Episode 1 that he had rushed into a relationship, sharing more details about it. “It was just [that] she made me feel whole again, and [it’s] unfair to her. But then, once I felt whole again, I was like, ‘Oh, I have more healing [to do],” he explained to Madison LeCroy during the episode. “I was just lonely, and I didn’t know how to be by myself. And I think that’s why I rushed into the first person I talked to. Like, I didn’t talk to anyone else. It was just her.”
RELATED: Craig Conover Responds to Accusations He’s a “Narcissist” (VIDEO)
Craig Conover’s fling with Kristin Cavallari
Prior to dating Paige, Craig had a very brief and casual fling with Kristin Cavallari. She opened up about this during a June 4, 2025 appearance on Watch What Happens Live with Andy Cohen. “Craig and I were friends first, we became romantic for two seconds,” she said. “The second I caught wind of Paige, I very politely excused myself from the situation. I saw the picture and I texted him, ‘Hey, let’s just be friends.’ Like, I don’t want to get in the middle of this. I was already in a love triangle in high school, I’m good for the rest of my life, I never want to be in another one. That’s it.”
Craig Conover’s romance with Charley Manley
Craig was first introduced to Charley Manley during Southern Charm Season 11. The two cast members quickly hit it off during the season, going on dates and kissing one another. But, during a cast trip to Mexico, things took a turn when Craig got into an argument with Salley Carson, causing Charley to lose interest in a future with him.Â
Craig made a major accusation toward Charley during Part 2 of the Southern Charm Season 11 reunion. “I was strung on. I can’t believe I know what this means now…I was love bombed,” he said. “You said all this stuff for me. And, like, you were FaceTiming me from your friends’ weddings and started to be the talk of the town. But then I was like, ‘Oh my God, this is what love bombing is.’…There was some future planning on your end.”
What’s in store for Craig Conover on Southern Charm Season 12
Viewers will get to see Craig become even more invested in his career and his friendships rather than his love life during the new season. According to an announcement for Southern Charm Season 12, “back in Charleston and ready to rebuild, Craig prepares to add author to his resume with his first children’s book. He finds himself cautiously reentering a friendship with Austen, which threatens to derail some others.”
See what else is in store for Craig and his career in the Southern Charm Season 12 trailer.
— Reporting by Tom Sutch
