Southern Charm Season 11 kicked off roughly five months after Craig Conover and Paige DeSorbo ended their relationship — but reminders of the breakup still lingered.
When Madison LeCroy stopped by Craig’s home for a catch-up session during the Season 11 premiere, she noticed some painting supplies on his porch and asked if he had been trying to channel artist Bob Ross.
“No, it’s a remnant of the past chapter,” Craig explained, referencing his three-year relationship with the Summer House alum. “Paige used to sit out here in her bathing suit and just paint.”
He went on to share more “honest” insight into his post-breakup state of mind, both to Madison and in a confessional.
RELATED:Â Craig Conover Makes a Big Statement on His Dating Life at BravoCon 2025 (VIDEO)
“I was betrayed by the person I trusted most in this entire world,” Craig said in a producer interview. “I mean, we had our whole future planned.”
As the Sewing Down South co-owner elaborated to Madison, “It’s been a journey. I will say that I’ve hit a level of sadness that’s not depression-based; it’s more like bummer-based. Because I, like, never did anything to deserve becoming the villain in her story, but she needs a villain.”
Craig Conover opened up about dating, post-breakup
Regardless, Madison noted that Craig seemed “good,” prompting him to bring up that he had “started to see someone else.” Though he didn’t mention her by name, onscreen headlines revealed that Craig was referring to his brief romance with Natalie Buffett that he’d discussed on Watch What Happens Live with Andy Cohen in March 2025.
“We met in the Bahamas like six years ago and we reconnected,” Craig shared. “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].”
In a confessional, he added, “I had seen, like, my ex move on. I didn’t know what to do.”
RELATED: Craig Conover and Naomie Olindo Reunite for “Epic” Moment Together: “Look at Us Now”
As Craig put it to Madison, “I was just lonely, and I didn’t know how to be by myself. I think that’s why I rushed into the first person I talked to. … I didn’t talk to anyone else. It was just her.”
Madison, for her part, suggested that Craig embrace his single status and start to “date around” a bit.
“I think I need to get to know someone for a little bit before I get, like, intimate with them,” Craig replied, admitting that he was “a little nervous” that, at 37 years old, he might have already aged out of the Charleston dating scene.
“A lot of people say you have three true loves,” he remarked in a confessional, mentioning that he’d already had two, Paige and Naomie Olindo. “So, I’m just kind of holding onto that.”
Craig Conover showed a romantic interest in Salley Carson
Later, at Madison’s baby shower, Craig joked to his friends that he had a “huge void to fill” with “partying” and “girls.”
“I’m starting to remember who I was before my last relationship,” the Southern Charm-er added to a producer. “I do not want to go back to that person necessarily. But I was confident and, like, I was good at hanging out with girls.”Â
During another one-on-one chat with Madison mid-party, Craig remarked that castmate Salley Carson was “fun,” prompting Madison to ask, “But she’s not your type, right?”
“No, I think she’s beautiful,” he answered. “Salley and I would probably have a lot of fun together. Who knows what would happen?”
As Madison weighed in, “I mean, you’re single now. Why not?”Â
As he begins to navigate the Charleston singles scene, find out how Craig and Salley teased their rocky Season 11 romance during BravoCon 2025.
