Paige DeSorbo and Craig Conover's Relationship Timeline

Paige DeSorbo and Craig Conover first met while filming the Bravo reality series Summer House

For years, reality TV stars Paige DeSorbo and Craig Conover orbited one another in the Bravo universe.

The pair first crossed paths in the Hamptons while filming Bravo's hit reality show Summer House, and later developed a close friendship on the spinoff series Winter House. At the time, DeSorbo had recently split with ex Perry Rahbar, and Conover was dating his then-girlfriend Natalie Hegnauer.

Their friendship turned romantic shortly after filming wrapped for Winter House, though both DeSorbo and Conover continued to see other people while they explored how serious their feelings were — a journey that was well documented during season 6 of Summer House.

Craig Conover, Paige DeSorbo LIVE WITH ANDY COHEN -- Episode 19053 --
Charles Sykes/Getty

However, it didn't take long for the duo to realize they wanted to be together. The couple made things official in October 2021, and have been giving fans a glimpse into their romance on social media ever since.

From their Winter House friendship to their Summer House love triangles, here is a complete timeline of Paige DeSorbo and Craig Conover's relationship.

Summer 2019: Paige DeSorbo and Craig Conover meet

Paige DeSorbo, Craig Conover
Paige DeSorbo, Craig Conover. Paul Morigi/Getty; Alberto E. Rodriguez/Getty

DeSorbo and Conover first crossed paths during season 4 of Summer House. Members of the Southern Charm cast, including Austen Kroll and Conover, appeared as guests on an episode of Summer House when they attended a birthday party for star Kyle Cooke.

February 2021: Paige DeSorbo and Craig Conover establish a friendship on Winter House

Less than two years later, DeSorbo and Conover became costars when they filmed the first season of Winter House in Vermont alongside Summer House's Cooke, Amanda Batula, Lindsay Hubbard, Luke Gulbranson and Ciara Miller. They were also joined by newcomers Andrea Denver, Julia McGuire, Gabrielle Kniery and Jason Cameron, along with Conover's Southern Charm costar Kroll.

The cast spent 17 days filming the show in February 2021, during which DeSorbo developed a flirty relationship with Denver while Conover was busy missing his then-girlfriend Hegnauer.

April 2021: Paige DeSorbo visits Craig Conover in Charleston

After filming the show, DeSorbo visited Charleston, South Carolina,where Conover lives. While she took the trip with friends, fans quickly assumed that the Summer House star was also there to see Conover.

DeSorbo addressed the rumors during an appearance on the Not Skinny But Not Fat podcast that month.

"Craig and I are a thousand percent not dating," she said at the time. "Craig and I have known each other for years. We've always gotten along. We've always been friends. We have, like, very similar personalities. We are not romantically involved or anything, but we are very good friends."

However, DeSorbo later revealed to ET Online that during her trip, she and Conover took a small step out of the friend zone and shared their first kiss.

"On that trip, I realized that Craig was single – and we were nothing but friends on that trip – and then the last night he kind of kissed me," she said. "I actually said, 'It's crazy that you haven't kissed me yet,' and he was like, 'I didn't know where we were at that point.' "

June 2021: Paige DeSorbo and Craig Conover film Summer House

DeSorbo began filming the sixth season of Summer House towards the end of June 2021. While Conover had yet to announce if he'd be making a guest appearance at the time, fans of the reality show speculated that the Southern Charm star would likely pop up given his and DeSorbo's rumored romance.

August 19, 2021: Paige DeSorbo and Craig Conover attend the PGA Tour together

Paige DeSorbo and Craig Conover
PGA Tour

In August 2021, DeSorbo and Conover were spotted at the PGA Tour's FedExCup Playoffs together at the Liberty International Golf Course in New Jersey.

Though the nature of their relationship was unclear at the time and the duo did not display any PDA at the event, fans quickly began speculating that the reality stars were officially an item.

September 25, 2021: Paige DeSorbo and Craig Conover attend their costars' wedding

Although they had yet to confirm their relationship, DeSorbo and Conover added even more fuel to the romance rumors when they both attended Cooke and Batula's wedding. DeSorbo served as a bridesmaid at the event, and shared a photo booth snap of her and Conover on her Instagram story.

October 2021: Paige DeSorbo and Craig Conover make their relationship public

After months of speculation, DeSorbo and Conover officially went public with their relationship in October 2021. During an interview with PEOPLE, Conover gushed over his costar-turned-girlfriend and said that their romance was a long time in the making.

"We both had a crush on each other from three years ago when I came to the Hamptons for Kyle's birthday party," he said. "We always had an eye for each other."

He went on to reveal how their relationship turned romantic, maintaining that it happened "naturally."

"It was done in a healthy way. We built a friendship and got to know each other first, and it all happened naturally," he said. "You see the foundation of our relationship start to form on the show."

As for why they kept their romance under wraps for so long, Conover said that he and DeSorbo wanted to stay out of the public eye while they navigated their early days as a couple.

"It confuses me when people didn't think it was real or that we were hanging out for publicity," he said. "If it wasn't real then I'd be posting about it. I haven't posted a thing about it because it's so real."

November 2021: Paige DeSorbo discusses her relationship with Craig Conover

Craig Conover, Paige DeSorbo
Charles Sykes/Bravo/NBCU Photo Bank via Getty

A month later, DeSorbo discussed some of the backlash her relationship with Conover had received on an episode of the Call Her Daddy podcast.

"The number one thing that's really been pissing me off is people are like, 'Oh they're just acting and they're doing this as a PR stunt,' " she said. "If that was true, I would straight Ben and Jen this s— and be posting it all over and I'd have the best captions to everything."

DeSorbo also explained why she still hadn't made the relationship Instagram official yet, saying, "The only reason I haven't posted him is I haven't taken a grid-worthy pic."

She added, "And this is my real-life boyfriend, you're not posting your boyfriend on your Instagram until he says, 'I love you.' "

During an interview on E!'s Daily Pop that same month, DeSorbo shared that she and Conover were spending the holidays with each others' families. At the time of the interview, the couple had just celebrated an early Thanksgiving with Conover's family in Delaware, and were heading to Albany, New York together to spend the holiday with DeSorbo's relatives.

When asked about a possible engagement in the near future, DeSorbo joked, "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!"

December 8, 2021: The Summer House season 6 trailer drops

The trailer for Summer House season 6 dropped in early December 2021, and teased an in-depth look at the beginning of DeSorbo and Conover's romance.

December 19, 2021: Paige DeSorbo makes her relationship with Craig Conover Instagram official

paige desorbo
paige desorbo/instagram

DeSorbo finally made her relationship with Conover Instagram official in December 2021. She posted a glamorous photo of the couple at a holiday event with the caption, "Sew in love" — a nod to Conover's merchandise company, Sewing Down South.

January 11, 2022: Paige DeSorbo and Craig Conover enjoy a winter weekend together

Paige DeSorbo and Craig Conover in Aspen, CO
Craig Conover Instagram

In early January, Conover and DeSorbo took a ski trip to Aspen with some of their friends. Conover shared a few sweet snaps of the couple together throughout the weekend, as well as a video of them riding down the mountain.

"So I kinda love this stuff," he captioned one of the posts.

January 2022: Summer House season 6 premieres

Summer House

With the premiere of Summer House season 6, fans finally got to watch the early stages of DeSorbo and Conover's relationship. In classic Bravo nature, their budding romance was not without challenges and drama.

Since DeSorbo and Conover had yet to define their relationship during filming, viewers saw the duo try to navigate casually seeing other people as they figured out where they stood.

During one episode, DeSorbo discussed the potential love triangle that was brewing between her, Conover and her Winter House fling Andrea Denver.

"I really like Craig, but I also like Andrea," she told Batula, who responded, "It seems like you got yourself into a pickle."

Their relationship hit another roadblock when Hubbard told DeSorbo that Conover had been hooking up with Kristin Cavallari. Conover and Cavallari had first sparked dating rumors when they were spotted together in Nashville, though they later denied that they were seeing each other.

craig and paige on summer house

While Conover responded by telling members of the Summer House cast that he and DeSorbo could "hook up with whoever," DeSorbo told Conover that the hookup rumors made her "look stupid."

During an interview with ET Online, DeSorbo later explained that this period of turmoil helped her sort out her feelings for Conover.

"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," she recalled. "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."

February 14, 2022: Craig Conover supports Paige DeSorbo on Valentine's Day

For their first Valentine's Day together, Conover made a surprise appearance during DeSorbo's live shopping event on Instagram. The couple answered fan questions about their relationship during the virtual event, and discussed their long-distance romance, their future plans, and the story of how they first met.

Conover told viewers that he already had a crush on DeSorbo when he showed up to her Hamptons share house and asked her to go on the water slide with him. "We ran up the water slide, went down the water slide, and then she walked away and didn't talk to me for like two years after," he said, to which DeSorbo cheekily replied, "And now we're dating."

DeSorbo later gave Conover a shoutout in the caption of her post about the event, thanking him for the surprise appearance.

March 2022: Paige DeSorbo celebrates Craig Conover's first book launching

DeSorbo returned the favor and showed her boyfriend support when Conover released his debut memoir, Pillow Talk: What's Wrong with My Sewing?, in March 2022.

She marked the occasion with several sweet Instagram posts, and Conover told PEOPLE during an interview that his girlfriend's support "is everything."

"Paige just sent me flowers to my hotel room because it's launch day. I'm opening them right now," he said. "She's a great teammate and partner. She's an incredibly supportive person. She's so sweet."

Conover also shared that he was nervous at first about DeSorbo reading the book, but noted that she loved it.

"[Paige] flew through the first couple of chapters and she said she cried when she read about my experience with bullying," he said. "I think it helped her have a deeper understanding of who I am."

March 25, 2022: Craig Conover discusses his future with Paige DeSorbo

Paige DeSorbo, Craig Conover LIVE WITH ANDY COHEN -- Episode 19053 --
Charles Sykes/Getty

In a conversation with Page Six, Conover shared that he and DeSorbo are already planning a future together.

"We have talked about marriage and spending our lives together, which we're happy about," he said. "We talk about kids and a family."

On an episode of the Reality Life with Kate Casey podcast, Conover revealed that the couple eventually wants to live in the same city and move in together, but said they aren't in a rush right now to make those decisions.

"I think we would be in Charleston, but I don't think she'll ever not have an apartment in New York," he said. "We're just in a fortunate place where we don't really have to make those hard cut decisions. We're just both so busy right now and traveling. And now, we're getting to start to work together on projects outside of TV, which is really fun."

March 29, 2022: Craig Conover says he is crazy about Paige DeSorbo

In late March, Conover opened up again about his relationship with DeSorbo during an interview with ET Online.

"I've kind of always searched for a partner and a teammate to share this stuff with, and I couldn't have found a better one and it's really nice," he told the outlet. "She has so much going on, with her clothing line laughing and stuff happening that we get to celebrate each other's wins. And it's kind of a unique thing that comes with being in this business together. And we're just enjoying it."

He went on to say that this relationship feels "more mature" than past ones, and shared that he and DeSorbo have been having serious conversations about their romance and where it's headed.

"It's an adult relationship," Conover said. "We talk about marriage and having kids and the things we agree on — and don't disagree on — and we really hope to be married."

April 24, 2022: Paige DeSorbo and Craig Conover attend a wedding together

Paige DeSorbo and Craig Conover at a Wedding
Paige DeSorbo Instagram

DeSorbo and Conover attended his Southern Charm costar Dustin Johnson's wedding to Paulina Grettsky alongside several other Bravo stars. DeSorbo shared a series of photos of the couple looking dapper in front of a floral display with the caption, "Getting 'the shot' is a full time job."

April 25, 2022: Craig Conover says Paige DeSorbo is moving to Charleston for the summer

After being long-distance for most of their relationship, Conover told that DeSorbo will be living with him in Charleston, South Carolina, for the summer. The Southern Charm star shared that he's preparing for the temporary move by making his home less of a bachelor pad.

"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 said. "I'm getting it ready to live in with a partner."

He also added that he hopes the move will eventually become permanent.

"We're excited to move in together eventually. That's definitely the direction we're headed," he said.

May 7, 2022: Paige DeSorbo spends a day at the beach with Craig Conover's family

Paige DeSorbo and Craig Conover in Charleston
Craig Conover Instagram

Ahead of DeSorbo's temporary move, the couple enjoyed a beach day in Charleston, South Carolina, with Conover's parents. Conover shared a series of photos on Instagram from the occasion, including a sweet selfie of him, Desorbo and his parents. And, of course, his company's pillows were a staple in their beach picnic spread.

June 2022: Craig Conover talks potential spinoff with Paige DeSorbo

Conover and DeSorbo exclusively opened up to PEOPLE about their feelings towards having their own TV show when they hit the MTV Movie & TV Awards: UNSCRIPTED red carpet.

Though DeSorbo did acknowledge that taking on their own series would be "a lot of pressure," Conover didn't hesitate to say, "I would do it."

"I think [our own show] would be funnier than both Southern Charm and Summer House," DeSorbo admitted. The Sewing Down South founder added, "I think it'd be fun to see us in our off time."

DeSorbo said that, despite the "pressure" of having her love life play out across multiple reality TV shows, "I feel like it actually keeps us in line because everyone's gonna see us, including our parents."

June 2022: Craig Conover says his long-distance relationship with Paige DeSorbo is "getting harder and harder"

In an interview with Page Six, Conover opened up about living in different cities from his girlfriend. "You know, long-distance is working for us," he said. "We're fortunate that we're on the East Coast, so it's only an hour flight, but it is getting harder and harder."

"She was just gone for 10 days in Italy, and that was tough," he added. "But we're starting to see the amount of time that we're spending chisel away to only a couple of days. So, you know, we'll see."

August 23, 2022: Craig Conover reveals his dream wedding is "completely different" than Paige Desorbo's

In an interview with E! News, Conover shared what his ideal wedding would be, although he admitted that DeSorbo's wedding dreams might not align with his.

"Paige's vision is completely different than mine," Conover explained. "The reason I ended up moving to the Bahamas for that year or two was because of a wedding I went to in Abaco and when you got to the wedding, everyone was barefoot … It was just so laid back and everyone spent a week there."

He continued, "I want to have a big welcome crab feast when everyone gets there, and then I want to have the rehearsal dinner on Thursday, a party Friday and the wedding Saturday and a brunch Sunday ... But you know, I am just a boy that has never really looked into all of this."

He added that his girlfriend "doesn't want a beach wedding" but is "OK with it being like a four- to five-day experience."

"I think her vision is somewhere in Italy," he said.

September 15, 2022: Paige DeSorbo says she's "f---ing terrified" of living with Craig Conover

Paige DeSorbo and Craig Conover attend the Heineken suite at the US Open Tennis Championships
Craig Barritt/Getty Images for Heineken

A trailer for the second season of Winter House was released, showing a glimpse of the stars of Summer House, Southern Charm and Vanderpump Rules living together in Vermont. The crew is seen drinking and partying, though it seems not everyone is excited about the extended time in one house.

In the trailer, Conover says, "This will be the longest Paige and I have ever spent together."

Meanwhile, DeSorbo admits, "I'm not used to living with a boyfriend," adding, "I'm f---ing terrified."

October 13, 2022: Craig Conover says he and Paige DeSorbo will settle down in Charleston

Conover and DeSorbo are currently maintaining a long-distance relationship as she lives in New York City and he lives in Charleston, South Carolina.

While chatting with E! News, Conover shared the couple's hypothetical plans for the future.

"Eventually, when we get to the point to have kids, that will be in Charleston," he said. "But her career is taking off in New York right now and I love it up here."

Conover continued: "I do know that for the next few years we'll be spending a lot of time [in N.Y.C.]. Also, it's not my decision, so we'll see what Paige wants to do. I love it up here, but I think as we start to move in that more settled-down direction, it will be further south."

October 14, 2022: Craig Conover reveals he'll propose whenever Paige DeSorbo "is ready to say yes"

BRAVOCON -- Modern Love Panel from the Javits Center in New York City on Friday, October 14, 2022 -- Pictured: Diana Silvers and Craig Conover -- (Photo by: Monica Schipper/Bravo via Getty Images)
Monica Schipper/Bravo/Getty

During BravoCon 2022's Modern Love panel, Conover shared that he'd propose to DeSorbo "whenever Paige is ready to say 'yes.' "

"I have a feeling that we're going to end up getting married one day," Conover said. "It'll be great. I don't know if she knows that. I think you'll get to see it actually come out on one of the shows."

However, the reality star admitted that geography is a complicating factor, with DeSorbo in N.Y.C. and himself in South Carolina. "The thought of leaving and going to a new state is a lot for me, so I have to do it when I'm ready," DeSorbo said.

Still, Conover revealed that the two are progressing in their relationship. "I have my own closet in Paige's house now," he said.

November 3, 2022: Paige DeSorbo thinks Craig Conover overreacts to his Capture the Flag injury

In a sneak peek of an episode of Winter House, the housemates played Capture the Flag. In the clip, Conover fell and hits his knee on a rock, causing him to bow out of the game. "I'm not playing in this f---ing rock field anymore," he said.

Other members of the house, including DeSorbo, seemed to think his reaction was a little too dramatic. "I went face first into a table — got up, won the game, kept it moving," she said. "Craig hit his poor little knee on a rock? Game's over."

December 20, 2022: Paige DeSorbo and Craig Conover travel to Albany for the holidays

Conover documented his travel journey with DeSorbo as the pair headed to DeSorbo's hometown of Albany, New York. The reality star shared a series of videos on his Instagram Story, including a clip of DeSorbo riding an airport escalator. Over the video, he listed the airport codes CHS, ATL and ALB with airplane emojis in between. He also included "#travelswithcraigandpaige."

Other clips included Conover talking about the flight being delayed and a video of himself walking around the airport in search of donuts for DeSorbo.

February 16, 2023: Paige DeSorbo opens up about her and Craig Conover's long-distance relationship

Paige DeSorbo and Craig Conover attend the 2022 MTV Movie & TV Awards: UNSCRIPTED
Rich Polk/Getty

DeSorbo spoke about how she and Conover make their relationship work, despite her living in New York City and him being in Charleston, South Carolina.

"Long distance is definitely not an easy thing to do, but I will say, I think Craig and I handle it very well," DeSorbo told PEOPLE. "Obviously we will argue about certain things, but I love being with my friends during the summer. I love living in New York. I love going to the Hamptons on the weekends. He's very supportive of that."

The reality star added that she doesn't currently have plans to move to Charleston but says that she and Conover have discussed living together. "I really do love my life the way it is. And we talk about what will happen in the future," she said.

April 3, 2023: Paige DeSorbo cries over moving to Charleston for Craig Conover

In a midseason trailer for Summer House season 7, DeSorbo and Conover are seen discussing her potential move from New York City to Charleston.

"I would be changing my whole life. I have no friends in Charleston. My whole career is [in N.Y.C.]," DeSorbo says while wiping away tears.

May 8, 2023: Paige DeSorbo says Craig Conover seems "insecure" about their relationship on an episode of Summer House

Paige DeSorbo, Craig Conover
Charles Sykes/Bravo/Getty

DeSorbo and Conover talked about their relationship in a season 7 episode of Summer House, with Conover noting that the pair are "working towards taking our two life courses and blending them into one collected course."

In a confessional, DeSorbo discussed their situation further. "I think when I say things to Craig like, 'I'm fine being independent and I don't want to move to Charleston and I don't want to get engaged yet,' he gets very insecure, which valid. Totally get it," she said. "But that is stressing me out."

May 15, 2023: Craig Conover says he and Paige DeSorbo "have more stuff to work out" before getting engaged

On an episode of Summer House, Conover spoke to DeSorbo's best friend, Ciara Miller, about his girlfriend's hesitations about getting engaged.

"To her, being engaged, moving in together, leaving her mom, and she's not wrong by saying eventually we're gonna have to talk about that," Conover said. "I have realized that we have more stuff to work out than we thought."

Later in the episode, the pair revealed more issues in their relationship when they had a spat that ended with Conover taking off his mic and throwing it. The next day, DeSorbo called her boyfriend "a baby."

"Craig always acts so dramatic and then like, it's my fault, and I'm like, 'I don't even know what's going on.' Then he gets mad because I'm not sensitive," she said.

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