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‘Southern Charm’ Star Craig Conover’s Dating History: Naomie Olindo, Paige DeSorbo and Moreee

   

Whether it’s his Bravo connections or more under the radar relationships, Craig Conover’s love life has been making headlines since Southern Charm’s 2013 premiere.

Conover had a flirty relationship with costar Kathryn Dennis during season 1 but he was friend-zoned before it turned romantic. By season 3, however, he had a full-fledged girlfriend in Naomie Olindo.

Following their 2017 split, Conover raised eyebrows for an alleged hookup with Kristin Cavallari before dating Summer House’s Paige DeSorbo for three years. With every relationship, Conover has remained committed to finding his forever love.

“I really only had rom-coms to base life off of,” Conover exclusively told Us Weekly in September 2023 of his dating philosophy. “I thought you dated, there was a conflict, and you got engaged after you made up and you got married.”

He has also remained adamant that he wants to settle down and be a dad. “I want that storybook life,” Conover said during a November 2023 episode of Southern Charm. “I do want the white picket fence.”

Scroll down to see Conover’s dating history:

Olindo met Conover prior to 2015 while attending the College of Charleston. She joined Southern Charm for season 3, which aired in 2016, as Conover's girlfriend. The pair moved in together during season 4, but after butting heads — and Olindo famously slamming Conover for his love of sewing — they called it quits in fall 2017. They were together less than three years. In May 2022, DeSorbo seemingly confirmed that Conover and Olindo hooked up during the early days of her own romance with Conover — but there were no hard feelings. Olindo exclusively told Us in June 2022 that she had a Las Vegas fling with her ex. "It was sort of like a time and place thing where it's like, 'OK, I know you, I trust you, we were both, like, fresh off breakups,'" Olindo said, noting the hookup was in summer 2021 after she split from Metul Shah. "This is a really long time ago now, but it was never like, 'Oh, we need to get back together, blah, blah.' It was just like a comfort thing — a very temporary comfort thing."

 

Conover confirmed his relationship with Hegnauer in December 2020, hours before she made her Southern Charm debut. The reality star explained on the show that he met Hegnauer in January 2020 while in Aspen, Colorado. "I'm pretty sure I love this girl, and I haven't had this feeling since Naomie," he told the cameras at the time. The pair called it quits the following year, with Conover confirming on a May 2021 episode of his and Austen Kroll's "Pillows & Beer" podcast that he was single.

Rumors surfaced in July 2021 that Cavallari was involved in a love triangle with Kroll and Conover after Lindsay Hubbard claimed on Summer House that she heard the Laguna Beach alum hooked up with one of the Bravo stars. Conover alleged in the episode, which aired in January 2022, that Kroll "hates that I was making out [with Kristin]." (When the episode filmed in summer 2021 Conover and DeSorbo were just starting to see each other.) Cavallari denied at the time that she was anything more than friends with Conover and Kroll after getting close with them in 2020 following her divorce from Jay Cutler. Years later, Cavallari changed her story. "We were all really good friends for a while and we had a drunk night and we all posted some stupid Instagram dancing around and it got blown out of proportion," Cavallari said during a September 2023 appearance on Watch What Happens Live With Andy Cohen. "I'm still friends with them." When asked whether she and Conover ever "hooked up," Cavallari responded, "I may have been drunk one night and kissed Craig."

DeSorbo and Conover got close during season 1 of Winter House but didn't go public with their relationship until September 2021 while attending Amanda Batula and Kyle Cooke's wedding. Throughout their three-year relationship, DeSorbo made cameos on Southern Charm and Conover returned the favor, appearing on Summer House. DeSorbo announced in December 2024 that she and Conover called it quits, later revealing she broke up with him over Thanksgiving. DeSorbo remained in New York and Conover in Charleston, South Carolina, throughout their romance, which a source exclusively told Us played a part in their split. "Craig was ready for the next steps and had plans to propose to Paige. He was really pushing for the next steps and wanted to settle down with her," the insider told Us in December 2024, claiming, "Paige does not want to move to Charleston, and logistically it was never going to work out long term." The breakup was detailed during the Southern Charm season 10 finale, which aired in March 2025. At the time, Conover said he bought an engagement ring, but DeSorbo told him to "hold off" on a proposal, which never came. DeSorbo's side of the story will be covered on the Summer House season 9 finale, airing later in 2025.

Conover teased his and Buffett's relationship during a March 2025 appearance on Watch What Happens Live With Andy Cohen, saying, "I'm very happy." He revealed there was someone special in his life, adding, "When I date, I tend to date only one person at a time. I've been seeing someone. I've been reminded that the universe works in crazy ways, and everything happens for a reason." A source exclusively confirmed to Us that same month that Conover's mystery woman is Buffett, who previously dated NFL quarterback Dak Prescott and MLB pitcher Jack Flaherty. Conover confirmed in June 2025 that he was back on the market after a brief romance with Buffett. "I just wasn't ready to date but I didn't know that. There's no guidebook for this," he explained on "The Toast" podcast.

💔 Naomie Olindo (2015–2017, Brief Reconnection in 2021)

Craig met Naomie while studying at the College of Charleston, but their romance didn’t blossom until they were both starring in Southern Charm. Their relationship officially began in 2015 and quickly became serious—so much so that they moved in together in 2016 and Craig even gifted her a “promise ring” on the show.

However, cracks began to form. Naomie was vocal about Craig’s lack of ambition and accused him of being unmotivated. They broke up in 2017 after nearly three years. Despite their split, they briefly reconnected in 2021, which Craig later admitted was more of a “closure moment” than a rekindling.

💁‍♀️ Natalie Hegnauer (2020–2021)

Craig began dating Natalie Hegnauer in late 2020 after meeting during a trip to Aspen. Their relationship played out quietly but didn’t go unnoticed by Bravo fans.

In early 2021, Craig mentioned on his podcast that he was happy and excited about his future with Natalie. However, by May 2021, they had broken up. Craig confirmed the split and said they had grown apart naturally.

😘 Kristin Cavallari (Brief Fling, 2023)

In one of the more surprising revelations, Kristin Cavallari admitted on Watch What Happens Live that she shared a drunken kiss with Craig in 2023. While there was no serious relationship between them, fans went wild over the confession.

Kristin made it clear that it was just a fleeting moment and not something to read too much into—but it did add some heat to Craig’s already spicy dating record.

💘 Paige DeSorbo (2021–2024)

Craig’s most high-profile relationship was with Summer House and Winter House star Paige DeSorbo. The two first crossed paths on Winter House and started dating in October 2021.

Fans loved their chemistry, but their long-distance dynamic (Craig in Charleston, Paige in NYC) and differing views on commitment created tension. After nearly three years together, the couple called it quits in late 2024.

In July 2025, Paige was spotted holding hands with her new boyfriend, Joe D’Amelio, in Capri. Craig, meanwhile, reflected on the breakup, saying it made him re-evaluate his priorities and what he truly wants in a relationship.

👀 Natalie Buffett (2025 – Current Status: It’s Complicated)

In March 2025, Craig revealed during an appearance on WWHL that he was seeing someone “special.” That someone was later identified as Natalie Buffett—an influencer known for dating NFL quarterback Dak Prescott and MLB star Jack Flaherty.

However, fans were left confused when Natalie posted a cryptic Instagram Story in June 2025, saying she doesn’t “comment on past or present relationships.” Craig then clarified that they had dated, but stopped short of confirming anything current.

As of now, their relationship status remains uncertain—but fans are watching closely.

💬 Final Thoughts

Craig Conover’s love life has seen it all: long-term commitments, passionate flings, and on-screen drama that kept fans glued to their screens. Whether he’s sewing pillows or dropping truth bombs on Southern Charm, one thing’s clear—Craig’s heart is always in the spotlight.

What’s next for the Southern charmer? Only time (and maybe Andy Cohen) will tell.

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