“Southern Charm” star Craig Conover is opening up about his dating history and his struggles with being single following several high-profile relationships.
The Bravo star, 38, returned for the season 12 premiere of “Southern Charm” on November 12, giving viewers a closer look at his life after his breakup with former “Summer House” star Paige DeSorbo.
Conover has dated several women during his time on Bravo, including Naomie Olindo, Natalie Hegnauer and DeSorbo. He also had a brief relationship with influencer Natalie Buffett and went on dates with Charley Manley during season 11.
Now, Conover says he’s taking time for himself, even though he still hopes to get married and start a family.
During a conversation with his assistant, Jack, in the season 12 premiere, Conover admitted that spending time alone has been difficult.
“It’s really hard for me to use my pool by myself,” he said. “It’s a challenge of mine to, like, be good alone.”
Craig Conover Reveals Why He’s Staying Single After Paige DeSorbo Split
Conover and DeSorbo began dating in 2021 after connecting while filming season 1 of “Winter House.”
The couple publicly confirmed their relationship that September when they attended Kyle Cooke and Amanda Batula’s wedding together.
Their long-distance relationship became a storyline on both “Southern Charm” and “Summer House,” with the pair discussing marriage and the possibility of Conover moving to New York City.
However, DeSorbo announced their breakup in December 2024 after three years together.
Conover has since been candid about his desire to find someone and build a family.
“I think the viewers will get to see a 38-year-old who would love to have a family one day, and share his life with [a family] one day, starting to face these challenges of like, do you settle because you want a family? Or do you keep living your life hoping it will work out or that you’ll find your person?” he told Bravo Insider.
He added, “So I think there are more conversations that this generation is having with themselves, where people are single later in life now. But not based on not wanting to settle down.”
Conover also revealed that he traveled to Wengen, Switzerland, by himself in January 2026 to work on becoming more comfortable with being single.
“The goal of this trip was to really force myself into isolation,” he explained.
“And it taught me that even though I prefer having a girlfriend, because I’m very codependent, it’s okay if I’m by myself for a little bit longer.”
Who Has Craig Conover Dated Before ‘Southern Charm’ Season 12?
Before his relationship with DeSorbo, Conover dated Olindo, whom he met while they were students at the College of Charleston.
The pair began dating in 2015 and documented their relationship on “Southern Charm” beginning in season 3.
They moved in together during season 4 but ended their relationship in 2017.
Conover previously told Bravo Insider that they were simply “too different” to make their relationship work.
Despite their breakup, the former couple has remained friends.
“Naomie and I are friends now,” Conover revealed during an October 2026 appearance on “Watch What Happens Live with Andy Cohen.”
Conover later dated Hegnauer, confirming their relationship in December 2020.
“I’m pretty sure I love this girl, and I haven’t had this feeling since Naomie,” he said during season 7 of “Southern Charm.”
Their relationship continued while Conover filmed the first season of “Winter House,” but he confirmed he was single during a May 2021 appearance on Austen Kroll’s podcast.
Conover also had a casual fling with Kristin Cavallari before his relationship with DeSorbo.
Following his December 2024 split, Conover briefly dated Buffett and spent time getting to know Manley during season 11.
‘Southern Charm’ Star Admits His Busy Career May Be Connected to His Love Life
Conover’s dating life isn’t the only subject he discusses during the season 12 premiere.
The reality star also admits he’s been keeping himself busier than ever with work.
“I’ve worked more in the last six months than I ever have in my entire life,” he told Jack.
His assistant suggested that his packed schedule might be a way to avoid spending time alone.
“You just don’t want to be alone in your head. So you’re like constantly saying yes to everything,” Jack said.
Conover acknowledged the observation, responding, “I think that’s something I can work on.”
Outside of Bravo, Conover continues to expand his business ventures.
His Sewing Down South flagship store in Charleston celebrated its fifth anniversary in May 2026. He also operates the Charleston restaurant By The Way and event venue The Waverly with Kroll.
In September 2025, Conover launched Plaid Horse Productions, his own production company.
He has also moved into acting, starring in Bravo’s first original scripted microdrama, “Charmed by a Southern Monster,” which debuted in November 2026.
Catch Conover in all-new episodes of “Southern Charm” Thursday nights on Bravo.
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