Inside Craig Conover and Natalie Buffett’s Relationship: He’s ‘All In’

Craig Conover and Natalie Buffett’s romance might be new to fans, but their connection goes way back.

“Craig and Natalie met years ago and had a fling,” a source exclusively tells Us Weekly, noting that the hook up ended in 2019, meaning it was after Conover’s split from Naomie Olindo in 2017 and before he dated Natalie Hegnauer in 2020.

The insider says Conover, 36, and Buffett’s first rendezvous was “brief and not good timing.”

The Southern Charm star initially met Buffett, 27, through mutual friends and they “reconnected around the end of last year when they were both traveling in Colorado for New Year’s Eve,” the source shares.

Craig Conover 'Had Plans to Propose' Before Paige DeSorbo Breakup

“Craig wasn’t in a spot to date anyone seriously but loved reconnecting with her,” the insider tells Us, adding that Conover “always believes in signs and things working out if they are meant to be.”

Us previously confirmed that Conover celebrated NYE in Aspen with friends after Paige DeSorbo announced their split in December 2024. The couple dated three years before ending their relationship shortly after Thanksgiving that year.

Buffett — who previously dated NFL quarterback Dak Prescott and MLB pitcher Jack Flaherty — kicked off 2025 with a stay in nearby Vail.

Southern Charm's Craig Conover on Raya Dating App After Paige DeSorbo Split

In March, Conover teased his budding romance with Buffett, telling Andy Cohen on Watch What Happens Live that he was “very happy” and was dating someone new.

Us confirmed that same month that Conover’s new flame is Buffett, a model and social media influencer.

“They are taking things slow and it’s still pretty new, but Craig is all in,” the source told Us, adding that they had been seeing each other for a few months now and they’ve been spending time together in Charleston and New York City.”

Buffett “travels often,” according to the insider, who shares that the model is from Texas but “spends time” in New York and Florida.

“Craig is smitten and excited about the relationship,” the source continues.

The Sewing Down South founder “loves that Natalie likes being low key with him and they have been having fun together,” the insider adds.

“Everyone around him is happy that he is happy,” the source says, noting that Conover has been in “great spirits after a really rough breakup and his friends are supporting him.”

Craig Conover Hinted at Marrying Paige DeSorbo 2 Months Before Breakup

Prior to reconnecting with Buffett, Conover had several public relationships. He dated his Southern Charm costar Olindo, 32, for nearly three years before breaking up in 2017. He moved on with Hegnauer in 2020, but their romance fizzled out by spring 2021.

Conover and DeSorbo, 32, started dating that same year, going public that September. Their relationship highs and lows were featured on both Southern Charm and Summer House including the most recent seasons, which were filmed prior to their November 2024 split.

While Conover and DeSorbo have publicly traded jabs since their breakup, a source told Us on Tuesday, April 1, that the “Giggly Squad” podcast cohost “isn’t fazed by Craig dating.”

The insider added that DeSorbo “has been open to dating again, but is really focused on work.”

With reporting by Amanda Williams