Did Craig and Paige Hook Up? Details on the ‘Winter House’ Love Triangle

All is fair in love and Winter House — at least, that’s the case for certified lover boy Craig Conover. He previously dated his Southern Charm co-star Naomie Olindo for years until their 2018 breakup. Two years later, he met Natalie Hegnauer on vacation in Aspen.

In January of 2021, the couple debuted their relationship on Season 7 of Southern Charm, and Natalie relocated to be with Craig in quarantine. The duo previously expressed that being on lockdown together only strengthened their romance. But reports confirm that their love story didn’t last. So, why did Craig and Natalie break up? Here’s what we know.

In early 2021, Craig gushed that he and Natalie were still living together in South Carolina. However, Craig revealed their breakup in an episode of Pillows and Beer. He told his co-host, Austen Kroll, “I’m going through, like, [a] break up, and it’s nothing terrible, it’s just so easy to drink to avoid dealing with anything.”

Although their relationship has had its share of ups and downs, Craig and Natalie's split came as a surprise to fans. A month before his admission, the Winter House star confirmed that he and Natalie were still going strong. But he did mention that there was trouble in paradise. With both Craig and Natalie being on the move constantly, it wasn’t long before their relationship came to an end.

Craig said of their extended time apart, “We were just bummed that we’re going to be away from each other for so long, but then, as it goes on and as you’re doing this fun stuff and you’re seeing other people pair off and do their thing, you do start to miss your partner. So it was more just lonely and you wish they were there to kind of enjoy it.”

Since then, Craig has found love with another reality star — who just happens to be his Winter House co-star. Not long after Craig and Natalie broke up in May, he started dating Paige DeSorbo.

After months of speculation, Craig and Paige are officially dating. While Craig and Paige’s relationship evolved from platonic to romantic over the summer, they didn’t make their relationship official until later.

Despite rumors, the couple have been adamant that their relationship began after Craig and Natalie had already broken up. According to Paige, she and Craig met years ago when she was in a relationship and only started their romantic relationship recently.

“When we got to Vermont, I didn’t know he had a girlfriend. So, I was a little bummed when I first got there. But, of course, he was absolutely respectful to his girlfriend.” Paige told Us Weekly, “And I’m so happy now looking back that he had a girlfriend because we built just a very platonic friendship, which is, like, the base of our relationship now. Everything really does happen for a reason.”

You can watch new episodes of Winter House on Wednesdays on Bravo at 9 p.m. EST.