When Did Craig & Natalie Break Up? This Timeline Explains His 'Winter House' Status

- Winter House -
When Did Craig & Natalie Break Up? This Timeline Explains His 'Winter House' Status

Don't expect to see Craig Conover and Paige DeSorbo's relationship begin on Winter House. Despite the fact that the two Bravo stars have now officially confirmed their relationship, they were most definitely not together when filming Bravo's new Southern Charm-Summer House crossover event. In fact, according to Craig and Natalie Hegnauer's dating timeline, he was off the market the entire time he was in Vermont.

Winter House filmed for two weeks in February of 2021, when Paige was single, but Craig was, well, not. "When we got to Vermont, I didn't know he had a girlfriend," Paige told Us Weekly in an Oct. 18 interview confirming their current relationship. "So I was a little bummed when I first got there." Paige insisted that nothing happened between them while filming, saying they kept things "very platonic," but she also teased that things might have gotten complicated towards the end of their two week stay in the mountains. "You'll just have to see how it kind of plays out towards the end of our vacation," she said.

It sure sounds like things were a little more than just "platonic" in Winter House, but, as you can see by looking at Craig and Natalie's relationship timeline, it took a while for Paige and Craig to really act on their Winter House flirtation.

January, 2020 — Craig & Natalie Meet

This was kept hush-hush at the time, but when Natalie finally made her Southern Charm debut in December (see below), Craig confirmed that he first met his then-girlfriend in Aspen that January.

June, 2020 — Natalie Joins Craig In Charleston

After months of texting and being long distance during the pandemic lockdown, Natalie moved from Florida to Charleston to be with Craig, and the two quarantined with each other that summer.

October, 2020 — Craig Officially Confirms New Relationship

In October of last year, Craig finally confirmed he was in a serious relationship during an appearance on Bravo's The Daily Dish podcast. Though he didn't name Natalie at the time, he did say that the two were serious and opened up about their experience as a pandemic couple. "Learning how to be out of quarantine with each other has been a challenge," he said at the time. "I thought if you can quarantine together, that means you're fine,. But what [I didn't] realize is we were in the honeymoon phase, in a bubble, protected from the outside world." Craig also said that the decision to quarantine together after only dating for three months "put a lot of pressure on things."

Dec. 3, 2020 — Natalie Appears On Southern Charm As Craig's Girlfriend

Image: Bravo screenshot

Fans finally got to meet Craig's quarantine romance on Southern Charm in the Dec. 5 episode, "Monumental Challenge." She only appeared briefly, but Craig made it clear that the two were serious. "I'm pretty sure I love this girl," he said in the episode. "And I haven't actually had that feeling since Naomi."

January, 2021 — Natalie Defends Her Relationship With Craig Post-Southern Charm Season 7 Reunion

Natalie would appear in a total of five episodes in Season 7 of Southern Charm, and was a major point of contention at the Season 7 reunion when Craig's co-stars questioned her past hook up with Austen Kroll and her appearance on Andy Cohen's 2017 dating show, Love Connection. She later explained on Instagram that she only appeared on the dating show because her friend was a producer, noting that she wasn't interested in making reality TV her full-time gig. "I have a full-time job that I enjoy and have worked hard to achieve," she wrote, per Us Weekly.

In her statement, Natalie also dismissed any past relationship with Austen, calling it "a meaningless fling" and she even revealed that it was Austen who introduced her to Craig in the first place (long after the two had decided to be just friends.) "What I do in my private life is my decision and I should not be shamed for it," she wrote. "I understood from the start that in the world of reality TV this would naturally be brought up so I wanted to give you all my side," she concluded. "Craig is my best friend and we are happy together. Nothing else really matters."

Feb. 9, 2021 — Natalie Celebrates Craig's Birthday

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On Feb. 9, Natalie posted a sweet slideshow of photos celebrating Craig's birthday. "HBD to my pillow boy," she wrote in part. "Excited to be by your side as you knock another year out of the park :)."

Mid-February 2021 — March 2021 — Craig Films Winter House

Winter House reportedly filmed for about 17 days in mid-to-late February, after this birthday post. Craig has, as stated above, repeatedly insisted that he and Natalie were still dating when he filmed Winter House. In a later interview, Craig said that he would have wanted Natalie to come film with them, but that she was unavailable due to prior commitments. "She was on a ski trip in Park City with her friends that she already had planned," he told Us Weekly in April, adding that strict COVID protocols made even a visit from Natalie impossible while filming.

April 1, 2021 — Craig Confirms He & Natalie Are Still Together

A month after wrapping production on Winter House, Craig confirmed that he and Natalie were still going strong, despite rumors that he had gotten flirty with his Winter House co-star Ciara Miller. "Well, there's a lot that happens in Winter House, but no, I'm still with my girlfriend Natalie, here in Charleston," he told Us Weekly.

April 20, 2021 — Paige Denies A Relationship With Craig

After Paige was reportedly spotted hanging out in Charleston post-Winter House, she also had to clear up rumors regarding her relationship status. "Craig and I are a thousand percent not dating," she said during an appearance on the Not Skinny But Not Fat podcast on April 20, per Us Weekly. "Craig and I have known each other for years. We've always gotten along. We've always been friends.

May 1, 2021 — Craig Announces He & Natalie Broke Up

It's unclear when, exactly, Craig and Natalie broke up, but he confirmed the split during an episode of his Pillows and Beer podcast posted May 1. "I'm going through, like [a] break up," he said, adding that he was trying to deal with it productively instead of "[drinking] to avoid dealing with anything."

And, this all brings us up to now, mid-October of 2021, when Craig has officially confirmed he and Paige are dating — and have been for months. "We get each other, it's nice. We really are each other's biggest fans, which is something that I've always looked for," he told People on Oct. 18. In the same interview, he also promised that fans would get to "see the foundation of our relationship start to form on [Winter House]." I hope Natalie's not watching!

Image: Natalie Hegnauer/Instagram

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