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.

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.

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

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

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.”

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.”

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!”

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.

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.”

“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.”

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.”

“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.

“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.”

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.”

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.”

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

“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.’”

“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.”

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.”

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.

“We don’t post a lot together but she’s always by my side. It was really awesome having her with me on set,” Conover captioned an Instagram video of DeSorbo while referring to an upcoming movie appearance. “If anyone needs someone to run lines with, she’s your girl.”

DeSorbo admitted during an April 2023 episode of Summer House that the “thought of getting engaged and getting married and being someone’s wife is very f—king scary.” The following month, her relationship once again faced a bump in the road when Conover had his own doubts.

“Everyone in the world can see that something is wrong except the one person that I wanna see,” Conover told DeSorbo during the May 15 episode the show, which was filmed in September 2022, referring to his girlfriend seemingly ignoring how sad he was that he missed his mom’s birthday.

When the New York native confronted Conover about what he was crying about, he quipped: “Every time I get sad about something or I have a feeling, your response is, ‘Stop being a f—king p—y.’”

The businessman later confided in Cooke, saying, “I’m just sad. I just feel like I have to have a solid rock in my life.” While Cooke insisted that he had both his company and DeSorbo as something “solid” in his life, the Delaware native said, “Sometimes I just feel really alone.”

DeSorbo revealed to Elite Daily that she and Conover considered getting married during BravoCon weekend in Las Vegas. “I said, ‘Let’s go do it in a chapel,’” she recalled of the November getaway. “Craig chickened out, though.”

Conover was happy with his choice, explaining, “I’m not going to get married in Vegas. I want something more real than that.” DeSorbo joked, “What’s more real than me, you and Elvis, honey?”

The pair proved their relationship is going well — and full of trolling — on Valentine’s Day. “Life is this. I like this,” Conover wrote via Instagram, sharing a montage of moments with DeSorbo set to Anella Herim’s “Tennessee Love Song.”

DeSorbo initially poked fun at the over-the-top heartfelt tribute, writing in the comments, “CRAIG I’M ALIVE I DIDN’T DIE.” She added, “I take a nap for two hours and this is what happens on the internet.” DeSorbo added a third comment with three pink hearts, seemingly giving Conover the stamp of approval for the post.

Later that month, DeSorbo once again called out her boyfriend’s social media activity after Conover posted a sexy picture of himself after a gym workout. “Did you just post a thirst trap? We will talk when I get home,” she teased.