Craig Conover and Paige Desorbo are no more. Before Paige, Craig dated other starlets, like Naomie Olindo and Kristin Cavallari. Okay Craig did not date Kristin, but they did have a fling of sorts whilst Craig was between partners.
Paige and Craig lived in different chapters in separate books. Craig was ready to propose to Paige, but Paige began having second thoughts. Therefore, their relationship ended, causing Craig to allegedly return an engagement ring he had never had the chance to offer. He is now dating a model and influencer named Natalie Buffett.
Craig may be an unreliable narrator but he is ready to settle down and start a family. Perhaps Natalie will be his happily ever after? Either way, Craig has kissed many princesses on his way to the one. From Naomie to Natalie, these are the women who have held the heart of Craig.
Craig Conover started dating Naomie Olindo during Southern Charm Season 3
Naomie and Craig met long before Southern Charm existed. However, Naomie did not join this cast until Season 3. When Season 3 aired, Naomie waltzed into the scene with her cat, Gizmo, alongside an impeccable fashion sense and a slew of languages underneath her belt.
Craig and Naomie dated for roughly three years before calling it quits in 2017. Naomie left filming after Season 6, returning to this series in Season 8, where Craig had already moved on with Paige. However, before her return, and before Craig and Paige became monogamous, he and Naomie engaged in a “one or two-off situation,” as explained at the start of Southern Charm Season 8.
During Season 8, Episode 11, the cast gathered for Friendsgiving. Here, Naomie and Paige cleared the air on the porch. Craig immediately got stressed that they were chatting, labeling Naomie as his “crazy ex-girlfriend.” Even still, Paige and Naomie walked away from their chat in one piece.
Next, Craig Conover dated Natalie Hegnauer in Season 7 of Southern Charm
When Southern Charm Season 7 rolled around, Craig had a new lady on his arm. Natalie Hegnauer appeared in a few episodes at his side, where Craig readily made his feelings known to the viewers. Natalie loved his cooking and sewing, unlike his ex, Craig shaded, making her his next perfect fit.
Craig confirmed their relationship in December 2020, mere hours before Natalie made her Southern Charm debut. At the time, Craig was smitten, gushing, “I am pretty sure I love this girl, and I have not had this feeling since Naomie.”
Nevertheless, Craig and Natalie called it quits in 2021. “I am going through a breakup, and it is nothing terrible. [But] it is just so easy to drink to avoid dealing with anything,” Craig stated, emotionally distraught following their split.
Craig Conover engaged in a brief fling with Kristin Cavallari in 2021
Craig is to Bravo what Kristin is to MTV. In reality television, the stars of various series are often friends. They understand this world and the highs and lows that come with it, making connections easy to form. So, when rumors started surfacing involving a love connection between Kristin and Craig, this pairing made sense, that is, until the details emerged.
The headlines swore Kristin was entertaining a love triangle with Craig and his costar, Austen Kroll. At first, Kristin denied these allegations, while Craig remained coy. Years later, Kristin changed her tune.
Kristin appeared on Watch What Happens Live in 2023, admitting that she, Craig, and Austen were “good friends for a while. We had a drunk night, and we all posted some stupid Instagram, dancing around, and it got blown out of proportion.” Kristin and Craig kissed, but nothing more, she explained. This trio remains on friendly terms.
After growing close during Winter House Season 1, Craig Conover started dating Paige DeSorbo in 2021
Craig and Paige formed a tight bond during Season 1 of Winter House. By the time this season aired, their friendship had already evolved into a full-blown relationship. However, these two did not make their relationship status official until September 2021, while attending a wedding for her Summer House costars.
Paige and Craig dated for three years. During their relationship, Craig made cameos on Summer House. Likewise, Paige often traveled to Charleston, where she filmed scenes beside Craig on Southern Charm. Craig was allegedly ready to propose, but by late 2024, Paige began questioning their future as a duo.
The breakup closed out Southern Charm Season 10, which aired in March 2025. During the finale, Craig explained that Paige blindsided him with their split. While Craig was looking at their relationship with rose-colored glasses, many of their fans saw the truth as plain as day: these two were not compatible for a forever kind of love.
Craig Conover is now dating Natalie Buffett
Now Craig is with Natalie Buffett. Not wanting to put his Charleston cart before its horse-drawn buggy, Craig remained coy about his newest crush on a March 2025 appearance of WWHL. Here, Craig opened up to Andy Cohen in a teasing manner, only saying that he was happy. He then explained his new relationship a bit more, although he failed to reveal the name.
“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,” Craig shared.
Natalie, a 27-year-old model, was reportedly in the audience for this taping. Will Natalie and Craig go the distance? Only time will tell.
Southern Charm is streaming on Peacock.
TELL US – ARE YOU HAPPY CRAIG HAS FOUND LOVE AGAIN WITH NATALIE? DO YOU THINK NATALIE WILL APPEAR IN THE NEXT SEASON OF SOUTHERN CHARM?
