‘Winter House’ Stars Paige DeSorbo and Craig Conover’s Relationship Timeline

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'Winter House' Stars Paige DeSorbo and Craig Conover’s Relationship Timeline

Two Bravolebrities walked into a Winter House? Paige DeSorbo and Craig Conover were friends for years before their relationship took a romantic turn. The Southern Charm star and the Summer House personality crossed paths while starring on their respective Bravo shows. “I met Craig, actually, three years ago and he was single. I had a boyfriend and I absolutely respected that I was in a relationship,” DeSorbo told Us Weekly in October 2021, referring to ex Perry Rahbar. While they initially struck up a friendship, DeSorbo and Conover spent more time together in 2021 when they filmed Winter House. The Sewing Down South founder was dating Natalie Hegnauer at the time. “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,” DeSorbo told Us. “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.” [jwplayer D25bvzFs-l3ahXupL] After wrapping the crossover series, Conover and Hegnauer called it quits. He confirmed he was single in May 2021. Things between him and the fashionista were on by the summer, per insiders, and by the fall, the twosome were officially dating. “We actually love long-distance. We’re two people that are very independent and have so much going on during the week,” DeSorbo told Us in October 2021, noting she’s likely to pop up on Southern Charm, which was currently in production on season 8 in South Carolina. “When we get, like, Monday through Friday to get all of our things done and then I hop on a plane Friday morning, it’s fun. I feel like we’re more present with each other when we are together. We’re not on our phones and we plan and do fun things.” Conover, for his part, admitted that the twosome were crushing on each other ever since he filmed an episode of Summer House for Kyle Cooke’s birthday in 2019. "We are pretty happy now," he said in October 2021. "I don't think either of us has ever dated someone else in the industry. We get each other, it's nice. We really are each other's biggest fans, which is something that I've always looked for." Scroll through for a complete timeline of their relationship:

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February 2021

The twosome were joined by Cooke, Amanda Batula, Lindsay Hubbard, Luke Gulbranson, Ciara Miller, Austen Kroll, Andrea Denver, Julia McGuire, Gabrielle Kniery and Jason Cameron to film season 1 of Winter House for 17 days in February 2021.

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April 2021

After filming on the crossover series wrapped, fans were convinced something went down between DeSorbo and Conover in Vermont after she traveled to Charleston with friends. She denied they were dating during an April 2021 interview with Us.

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May 2021

According to insiders, things started to heat up between the twosome in May 2021.

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Summer 2021

The pair were hooking up during the summer of 2021. Conover was also spotted filming Summer House season 6 on multiple occasions.

Credit: Paige DeSorbo / Instagram

September 2021

The duo confirmed their relationship at Batula and Cooke’s September nuptials.

“We did get a little drunk at the wedding and threw a Story up there from the photo booth,” DeSorbo told Us one month later. “[But] I’m just waiting [for] the right scenery to happen to snap [an official] pic.”

Credit: Paige DeSorbo / Instagram

October 2021

While promoting season 1 of Winter House, DeSorbo gushed about Conover during an exclusive interview with Us.

“You’ll just have to see how it kind of plays out toward the end of our vacation. It sounds so cliché, but Craig just gets me,” she said. “There’s a lot of things I don’t have to explain to him because we look at things very similarly. It just fits, like, it just is very natural and it’s a lot of fun.”

Credit: Courtesy of Paige DeSorbo/Instagram

November 2021

During an interview with E!'s Daily Pop, DeSorbo shared that the pair celebrated Thanksgiving together with Conover's family in Delaware and her family in New York. When asked about a possible engagement in the future, she quipped, "I mean, we have only been dating for a couple of months. But if I can trick him into a diamond ring, I'm going to do it!"

Credit: Courtesy Paige DeSorbo/Instagram

December 2021

The couple became Instagram official after attending the season 8 Southern Charm wrap party in Charleston. “Sew in love,” DeSorbo captioned the snap, giving her boyfriend’s sewing skills and company, Sewing Down South, a shout-out.

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January 2022

DeSorbo and Conover’s love story will play out on the season 4 of Summer House, but their romance actually started a few months before filming in the summer of 2021. The New York native explained to Entertainment Tonight that she and Conover first kissed in April 2021 but were just “casually dating” in the months that followed — which viewers will see on the Bravo series.

DeSorbo was also keeping things casual with her Winter House flame, Andrea Denver, after the Vermont spinoff filmed in March 2021. She explained in January 2022 that she was single when the Summer House cameras started rolling in July 2021 — but she did find herself in a bit of a love triangle when Conover came to visit the Hamptons house and Denver was staying there too.

“Craig was not the reason I stopped hanging out with Andrea,” she told ET. "I was no one's girlfriend, so I was very much in the mentality of, I don't really owe any of these guys any explanation on my decisions because I'm not their girlfriend. So I definitely was playing the field all spring and certainly all summer."

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January 2022

"I can't pinpoint a certain thing that he did or said, it was kind of just realizing how I felt about myself when I was with him," DeSorbo told Entertainment Tonight as to why she started seriously dating Conover. "And it was just kind of undeniable. Little things that I would get excited — if I had a text message from him on my phone — and it didn't even compare to when other guys would text me. So I knew that I was very into him a lot more than any other suitors that were around."

She added: "We've had such a great six months already. We've talked about big things, just to see if we're aligned the way we feel about certain things — and we definitely are — but we're not even a year into our relationship. So, have we talked about a marriage and engagement, it's a normal conversation, but there's nothing very serious happening. We're only six months in."

Credit: Courtesy of Craig Conover/Instagram

January 2022

The couple enjoyed a night out in the Big Apple while Conover was in town visiting DeSorbo. “First Broadway show!” the southern gentleman captioned a snap of the pair outside of Disney’s production of Aladdin, noting that it was an “awesome night.”

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February 2022

“Do I look like someone who’s getting married on a beach? Does it look like I’m not going to wear shoes at my wedding?” DeSorbo exclusively told Us while attending the Sports Illustrated Proudly Presents The Party of her and Conover’s future wedding plans. “If we can see the ocean, I’ll compromise with that, but I’m not getting married on the beach.”

Conover, for his part, told Us that his girlfriend can have “whatever she wants” as long as the Bahamas is a possible venue spot, noting they’ve only been dating for seven months.

The Delaware native gushed about his girlfriend and their dynamic, saying, “We are each other’s biggest fan, so it really helped. I think I’m always rooting for her, she’s always rooting for me, which honestly goes really far in a relationship. Especially with our lives comes so many challenges.”

DeSorbo, for her part, recalled having a “crush” on her man for “three years” after seeing him on Southern Charm. Conover added that he “always had a crush” on his girlfriend. “I think so,” he concluded when Us asked whether DeSorbo is his person.

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March 2022

“I was upset for a while, but you gotta suck it up. It just is what it is at the end of the day,” the Pillow Talk: What's Wrong with My Sewing? author exclusively told Us about how his relationship with DeSorbo played out on season 6 of Summer House. “The fact that they made our relationship anything [negative] — it was pretty disappointing. I [had] just gotten out of a long-time relationship. She was doing her own thing and we lived in different cities and for three months we just, you know, we did our own thing and honestly it worked.”

Conover continued: “I really wished, you know, some more of the positive would've been focused on [with Paige]. At the end of the day, you let it go and it is what it is. … They cut our date because it was so positive and so happy that it wouldn't have made sense to show it. Those were the things that I was really upset about because Paige and I, we are a good example of a non-traditional relationship ending up in a really great place.” 

The southern gentleman further explained that while the beginning of the romance was “shown in a pretty dark light on television” they are now in a good place. “My parents [approve]. I don't think I would be allowed to be with anyone else if Paige and I didn't make it. My mom has decided that Paige is her daughter-in-law. And I feel the same about her parents,” Conover told Us. “We've only been officially dating for a little over six months … and no one ever plans on breaking up or bad things happening, but in our perfect world, yes, we'll get married and have a family.”

Credit: Shutterstock; Courtesy of Craig Conover/Instagram

April 2022

The businessman told BravoTV.com that his girlfriend would be joining him in Charleston for May and June to help him make decisions on his home renovations. "I'm having a ton of stuff done to my house, and she's definitely got an input on all those new changes, which really excites me," Conover told the outlet. "I'm getting it ready to live with a partner."

He added that while this stay is only “temporary” the duo are "excited to move in together eventually. That's definitely the direction we're headed.”

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May 2022

On an episode of “Behind the Velvet Rope with Davi Yontef,” the Southern Charm star warned fans that they shouldn’t expect an onscreen proposal from the couple. 

"I think if you guys ever saw it, the answer would be ‘No' from Paige. We do a good job of keeping…some of our milestones outside of the camera's reach,” the Delaware native said, adding: “You won’t see a proposal until we’re at least together for a year.” 

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June 2022

The Bravo stars looked smitten on the red carpet at the 2022 MTV Movie and TV Awards Unscripted.

Credit: Courtesy of Paige DeSorbo/Instagram

July 2022

“If people mutually hate us, it kind of brings us together,” DeSorbo told E! News in July 2022, noting she feels “lucky” to be dating a man who understands what it’s like to show off life on reality TV. “I'm like, 'Everybody hates us.' And he's like, 'Whatever, I love you.’"

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October 2022

“Honestly, Carl [Radke] and Lindsay getting engaged made everyone start asking me [about my own possible engagement], so I’m livid,” DeSorbo joked during BravoCon’s “Summer House in Autumn” panel.

The stylist then commented on her relationship with Conover after more than one year together. “But I am not in a rush to do anything. I feel like I really love where we are right now,” she explained, noting she recently gave her beau “closet space” which she called a “really big milestone.”

DeSorbo exclusively told Us during the New York City event that giving Conover “some room and a closet” was her “version of being engaged.” She recalled, “He was very, very happy. I mean, I thought he was gonna cry at [one] moment. He was like, ‘I can’t believe you did this for me.’ And I was like, ‘Stop. Don't make it a thing!’”

In all seriousness, DeSorbo told Us at BravoCon that the duo have come a long way since they started seeing each other. “I think the first year of your relationship is just, everything's so new and so fresh,” she revealed. “And especially to live, like, in this world that we live in and be able to experience BravoCon with each other, it makes it that much sweeter.”

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December 2022

Miller exclusively told Us that DeSorbo and Conover were “so good” after their ups and downs on season 2 of Winter House. She noted that the couple were “still so new in their relationship” when they filmed the reality show in early 2022.

“Now, I feel like they know each other so much better and they are more adjusted to kind of, like, what makes each other tick,” the nurse added.

Batula also weighed in on the duo’s TV struggles, exclusively telling Us, “He didn't need to wait to see things air and play out to realize what he did wrong or how he acted might have been inappropriate. ... ​ I think that's huge and the two of them have only grown since then. Closer and stronger.”

When it comes to the ​next steps, Batula revealed that she thought DeSorbo could eventually move to Charleston for Conover. “I feel like Paige will follow in her mom's footsteps of these amazing, like, dinner parties and plate settings and all of her holiday events,” she told Us. “I think that's what Paige wants and she'll get that down south.”

Credit: Courtesy of Paige DeSorbo/Instagram

February 2023

DeSorbo was all smiles as she cozied up to her boyfriend during a weekend getaway following rumors that they were on the rocks toward the end of 2022. The couple shared photos via social media while attending a pal’s wedding, including snaps of a day out on a boat together.