A Closer Look at the Relationship Journey of Paige DeSorbo and Craig Conover on 'Winter House'
Paige DeSorbo and Craig Conover's friendship blossoms into a romantic relationship Discover the timeline of their journey from February 2021 to December 2023
Paige DeSorbo and Craig Conover were long-time friends before their relationship turned romantic. The Southern Charm star and the Summer House personality first met three years ago while appearing on their respective Bravo shows. "I met Craig when he was single, and I had a boyfriend at the time. I definitely respected that I was in a relationship," DeSorbo told We exclusively in October 2021, referring to her ex, Perry Rahbar.
The friendship between DeSorbo and Conover grew stronger in 2021 as they filmed Winter House together. Despite Conover's previous relationship with Natalie Hegnauer, the two never crossed the line. However, shortly after wrapping the crossover series, Conover and Hegnauer called it quits. Conover confirmed his single status in May 2021, and by the summer, it was apparent that things were heating up between him and DeSorbo. By the fall, the pair had officially become a couple.
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"We actually enjoy being in a long-distance relationship," DeSorbo told Us in October 2021. "I believe we are more attentive and connected when we finally get to be together."
Continue scrolling to see a detailed timeline of their relationship:
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'Winter House' Stars Paige DeSorbo and Craig Conover’s Relationship Timeline
Paige DeSorbo and Craig Conover were friends for years before their relationship took a romantic turn.
The reality TV personalities from Southern Charm and Summer House first met while appearing on their respective shows. "I met Craig three years ago when he was single. I had a boyfriend at the time, and I respected that I was in a relationship," DeSorbo told We exclusively in October 2021, referencing her ex Perry Rahbar.
Although they started as friends, DeSorbo and Conover spent more time together in 2021 while filming Winter House. However, they did not cross any boundaries. Conover was in a relationship with Natalie Hegnauer at the time, but they broke up shortly after filming the crossover series.
In May 2021, Conover confirmed that he was single. By the summer, insiders revealed that things were on between him and DeSorbo, and by the fall, the two were officially dating.
"We actually enjoy the long-distance relationship," DeSorbo told Us in October 2021. "I feel like we're more attentive to each other when we're together."
Scroll through for a complete timeline of their relationship:
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February 2021
Season 1 of Winter House was filmed for 17 days in February 2021, with the participation of Cooke, Amanda Batula, Lindsay Hubbard, Luke Gulbranson, Ciara Miller, Austen Kroll, Andrea Denver, Julia McGuire, Gabrielle Kniery, and Jason Cameron.
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April 2021
After wrapping up filming on the crossover series, fans speculated that something happened between DeSorbo and Conover in Vermont when she visited Charleston with her friends. In an April 2021 interview with Us, she denied that they were dating.
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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
At Batula and Cooke’s wedding in September, the couple confirmed their relationship.
"We got a bit tipsy at the wedding and posted a Story from the photo booth," DeSorbo revealed to Us magazine a month later. "But I'm just waiting for the perfect moment to take an official picture."
Credit: Paige DeSorbo / Instagram
October 2021
While promoting season 1 of Winter House, DeSorbo gushed about Conover during an exclusive interview with Us.
"I'll have to wait and see how it all unfolds by the end of our vacation. It might sound cheesy, but Craig truly understands me," she explained. "There are so many things I don't need to clarify with him because our perspectives align. It just clicks, you know, it feels entirely natural and enjoyable."
Credit: Courtesy of Paige DeSorbo/Instagram
November 2021
During an interview with E!'s Daily Pop, DeSorbo revealed that the couple spent Thanksgiving with Conover's family in Delaware and her family in New York. When asked about the possibility of getting engaged in the future, she playfully commented, "Well, it's only been a few months since we started dating. But if I can manage to surprise him with a diamond ring, I'll definitely make it happen!"
Credit: Courtesy Paige DeSorbo/Instagram
December 2021
After making their first public appearance at the season 8 Southern Charm wrap party in Charleston, the couple officially debuted on Instagram. "Sew in love," DeSorbo wrote in the caption, giving her boyfriend's sewing expertise and his company, Sewing Down South, a shout-out.
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January 2022
DeSorbo and Conover’s love story will unfold in the season 4 of Summer House, although their romance began a few months prior to filming in the summer of 2021. The New York native revealed to Entertainment Tonight that she and Conover shared their first kiss in April 2021, but they were only "casually dating" in the following months— a storyline that viewers will witness on the Bravo series. DeSorbo also maintained a casual relationship with her Winter House flame, Andrea Denver, after the Vermont spinoff was filmed in March 2021. She clarified in January 2022 that she was single when the Summer House cameras started rolling in July 2021, but found herself in a bit of a love triangle when Conover visited the Hamptons house and Denver was also staying there. "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 had a wonderful evening in New York City while Conover was visiting DeSorbo. "First Broadway show!" the southern gentleman captioned a photo of the pair outside of Disney's production of Aladdin, describing it as an "amazing night."
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February 2022
DeSorbo expressed her aversion to a beach wedding, stating, "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?" She also mentioned a possible compromise if the ocean is visible, but made it clear she is not interested in a beach wedding. Conover, on the other hand, stated that his girlfriend can have "whatever she wants" as long as the Bahamas is a potential venue, acknowledging that they have only been dating for seven months. While attending the Sports Illustrated Proudly Presents The Party, they discussed their future wedding plans.
The Delaware native couldn't stop raving about his girlfriend and their strong connection, saying, "We're each other's biggest supporters, so it's made a huge difference. I'm always cheering her on, and she's always cheering for me, which is so important in a relationship, especially with all the challenges our lives bring."
DeSorbo, on her end, fondly remembered having a "crush" on her man for "three years" after first seeing him on Southern Charm. Conover also admitted to constantly having a crush on his girlfriend. "I think so," he confirmed when asked if DeSorbo is the one for him.
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March 2022
"I was frustrated for a period, but you have to tough it out. It is what it is in the end," the author of Pillow Talk: What's Wrong with My Sewing? exclusively told Us about the development of his relationship with DeSorbo on season 6 of Summer House. "The fact that they portrayed our relationship in a negative light was quite disappointing. I had just come out of a long-term relationship. She was doing her own thing and we lived in different cities. For three months, we just did our own thing and honestly, it worked."
Conover expressed his disappointment that the positive aspects of his relationship with Paige were not focused on. He was upset that their happy date was cut from the show because it was too positive, but ultimately accepts that "it is what it is." Despite their non-traditional relationship being portrayed in a negative light at the beginning, they are now in a good place and their parents approve of their relationship. Conover hopes to get married and start a family with Paige in the future.
Credit: Shutterstock; Courtesy of Craig Conover/Instagram
April 2022
The entrepreneur informed BravoTV.com that his girlfriend will be joining him in Charleston for the months of May and June to assist him in making decisions about his home renovations. "I have a lot of work being done on my house, and she is definitely providing input on all these new changes, which really excites me," Conover shared with the outlet. "I'm getting it ready to share with a partner." He also mentioned that while this arrangement is only “temporary,” the couple is "eager to eventually move in together. 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.
Paige would likely answer 'No' if you guys ever saw it. We make sure to keep some of our milestones away from the camera," the Delaware native said, adding: "You won’t see a proposal until we’ve been together for at least 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
DeSorbo shared with E! News in July 2022 that the mutual hatred from people actually brings her and her partner closer together. She feels fortunate to be in a relationship with someone who can relate to the experience of living life on reality TV. "It's like, 'Everyone hates us.' And he responds, 'So what? I love you.'"
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October 2022
"Carl and Lindsay getting engaged has everyone asking about my own engagement, so I'm not thrilled," DeSorbo joked at BravoCon's "Summer House in Autumn" panel. She then talked about her relationship with Conover after more than a year together. "But I'm not in a hurry to do anything. I'm really happy with where we are right now," she said, mentioning that she recently gave her boyfriend "closet space," which she called a "big milestone."
DeSorbo revealed exclusively to Us at the New York City event that giving Conover "some space and a closet" represented her "version of being engaged." She remembered, "He was extremely happy. I mean, I thought he was going to cry at one point. He was like, 'I can't believe you did this for me.' And I was like, 'Stop. Don't make it a big deal!'"
In a more serious tone, DeSorbo shared at BravoCon that the couple has made significant progress since they began their relationship. "I think the first year of your relationship is just, everything's so new and so fresh," she disclosed. "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
According to Miller, DeSorbo and Conover showed great improvement after their turbulent times in season 2 of Winter House. She mentioned that the couple were "still in the early stages of their relationship" during the filming of the reality show in early 2022.
The nurse commented, "They seem to know each other much better now and have become more attuned to what makes each other tick."
Batula also discussed the couple's TV struggles, telling Us exclusively, "He didn't need to wait for things to air and play out to realize his mistakes or inappropriate behavior. ... I think that's significant and they have only grown closer and stronger since then."
Batula shared her thoughts on the next steps, revealing her belief that DeSorbo could eventually relocate 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
During a weekend getaway, DeSorbo couldn't stop smiling as she snuggled up to her boyfriend, dispelling rumors of relationship troubles from the end of 2022. The couple took to social media to share photos from a friend's wedding, including pictures of their day out on a boat together.
Credit: Courtesy of Craig Conover/Instagram
April 2023
"We may not post together often, but she's always by my side. It was truly amazing to have her with me on set," Conover captioned an Instagram video of DeSorbo, talking about an upcoming movie appearance. "If anyone needs a line-running partner, she's the one to go to."
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May 2023
During an episode of Summer House in April 2023, DeSorbo confessed that the idea of getting engaged and married was incredibly frightening to her. The following month, their relationship hit another snag when Conover expressed his doubts.
"Everyone can see that something is not right except for the person I want to see it," Conover told DeSorbo during the May 15 episode, which was filmed in September 2022. He was referring to DeSorbo seemingly ignoring his sadness over missing his mother's birthday.
When the New York native asked Conover why he was crying, he replied, "Every time I feel sad or have a feeling, you tell me to 'stop being weak.'"
Later, the businessman opened up to Cooke, expressing, "I'm just feeling sad. I need a stable presence in my life." Cooke reassured him that both his business and DeSorbo were stable in his life, but the Delaware native admitted, "Sometimes I just feel very lonely."
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December 2023
DeSorbo disclosed to Elite Daily that she and Conover discussed the possibility of tying the knot during BravoCon weekend in Las Vegas. "I suggested, 'Let's just go to a chapel,'" she reminisced about the November trip. "But Craig got cold feet."
Conover expressed his satisfaction with his decision, stating, "I don't intend to get married in Vegas. I want something that feels more genuine." DeSorbo playfully quipped, "What's more authentic than the three of us - you, me, and Elvis, honey?"
