Paige DeSorbo and Craig Conover's Relationship Timeline — From Their Best Moments On-Screen Together to Their Amicable Breakup

Mar. 15, 2025

In a December 2024 episode of herGiggly Squadpodcast, DeSorbo announced that she and Conover had split, calling it “theright decision for both of us.”

The former pair first crossed paths in the Hamptons while filming Bravo’s hit reality showSummer House, and later developed a close friendship on the spinoff seriesWinter House. At the time, DeSorbo hadrecently split with ex Perry Rahbar, and Conover was dating histhen-girlfriend Natalie Hegnauer.

Their friendship turned romantic shortly after filming wrapped forWinter 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 ofSummer House.

Charles Sykes/Getty

However, it didn’t take long for the two to realize they wanted to be together. The former couple made things official in October 2021, and often gave fans a glimpse into their romance on social media while they were together.

From theirWinter Housefriendship to theirSummer Houselove 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.Paul Morigi/Getty; Alberto E. Rodriguez/Getty

DeSorbo and Conover first crossed paths during season 4 ofSummer House. Members of theSouthern Charmcast, includingAusten Krolland Conover, appeared as guests on an episode ofSummer Housewhen they attended a birthday party for starKyle Cooke.

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

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.

June 2021: Paige DeSorbo and Craig Conover filmSummer House

DeSorbo began filming the sixth season ofSummer Housetowards 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 theSouthern Charmstar would likely pop up given his and DeSorbo’s rumored romance.

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

PGA Tour

In August 2021, DeSorbo and Conover werespotted at the PGA Tour’s FedExCup Playoffs togetherat 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 attendedCooke 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 aninterview 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

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 theCall Her Daddypodcast.

“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 alsoexplained 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 aninterview on E!‘sDaily Popthat 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 19, 2021: Paige DeSorbo makes her relationship with Craig Conover Instagram official

paige desorbo/instagram

DeSorbo finallymade her relationship with Conover Instagram officialin December 2021. She posted a glamorous photo of them at a holiday event with the caption, “Sew in love” — a nod to Conover’s merchandise company, Sewing Down South.

January 2022:Summer Houseseason 6 premieres

Bravo

With the premiere ofSummer Houseseason 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 herWinter Housefling 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 whenHubbard told DeSorbothat Conover had been hooking up withKristin Cavallari. Conover and Cavallari had first sparked dating rumors when they werespotted together in Nashville, though they later denied that they were seeing each other.

bravo

During aninterview 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 then-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 thecaption of her postabout 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 then-boyfriend support when Conover released his debut memoir,Pillow Talk: What’s Wrong with My Sewing?,in March 2022.

Shemarked the occasion with several sweet Instagram posts, and Conovertold PEOPLE during an interviewthat his then-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

In aconversation withPage 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 anepisode of theReality Life with Kate Caseypodcast, Conover revealed that they 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.

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

Paige DeSorbo Instagram

In late March, Conover opened up again about his relationship with DeSorbo during aninterview 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 25, 2022: Craig Conover says Paige DeSorbo is moving to Charleston for the summer

Craig Conover Instagram

“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.

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

Inan interview withPage Six, Conover opened up about living in different cities from his then-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.”

September 15, 2022: Paige DeSorbo says she’s “f—ing terrified” of living with Craig Conover

Craig Barritt/Getty Images for Heineken

Atrailer for the second season ofWinter Housewas released, showing a glimpse of the stars ofSummer House,Southern CharmandVanderpump Rulesliving 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 14, 2022: Craig Conover reveals he’ll propose whenever Paige DeSorbo “is ready to say yes”

Monica Schipper/Bravo/Getty

DuringBravoCon 2022’s Modern Love panel, Conover shared thathe’d proposeto 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.

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

Rich Polk/Getty

DeSorbo spoke about how she and Conovermake 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.

May 8, 2023: Paige DeSorbo says Craig Conover seems “insecure” about their relationship on an episode ofSummer House

Charles Sykes/Bravo/Getty

DeSorbo and Conover talked about their relationship in a season 7 episode ofSummer 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 ofSummer House, Conover spoke to DeSorbo’s best friend, Ciara Miller, about his then-girlfriend’shesitations about getting engaged.

“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.

November 1, 2023: Craig Conover says he and Paige DeSorbo aren’t “rushing” to get engaged

Paige DeSorbo and Craig Conover at Bravocon 2023 in Las Vegas, NV on Saturday, November 4, 2023.David Becker/Bravo/Getty

David Becker/Bravo/Getty

While chatting with PEOPLE at BravoCon, Conover shared that the urgency to get engaged has waned for the them.

“It’s funny how things evolve and change,” he said. “I think there was so much pressure from the outside world. I love what we have now. My home base is Charleston and hers is New York, but if it was a Venn diagram, we cross over. We’re always together, we’re just in one place and the other.”

Conover added: “I think I’ve settled into a more sustainable flow of this is what works for us and let’s just enjoy it instead ofrushing into the next step.”

December 5, 2024: Craig Conover says he stopped drinking to show Paige DeSorbo he’s “husband and father material”

Paige DeSorbo and Craig Conover in 2024.Sara Jaye/Getty

Sara Jaye/Getty

Conover has “pretty much stopped drinking” in order to become “husband and father material” for DeSorbo.

“I could see it in Paige’s eyes that she saw the person I could be,” he told PEOPLE. “[Drinking] was always my priority, and I’ve found value in other things. It’s been a real blessing.”

TheSouthern Charmstar went on to add that he’s fully “committed to doing what it takes to make it work” with DeSorbo.

December 30, 2024: Paige DeSorbo reveals she and Craig Conover have broken up

During an episode of herGiggly Squadpodcast, DeSorbo told cohostHannah Bernerthat she and Conover had “decided to no longer be together,” though she added that she “wasn’t expecting this” to happen.

“I have so much love and respect for Craig. I think he is one of the best people I have ever met in my entire life,” DeSorbo said. “I will remain the biggest fan of him and want the best for him and he truly will get the best because he is the best. But with that said, I think it was just the right decision for both of us moving forward in our lives and the direction in our lives that we didn’t force.”

DeSorbo went on to call Conover “the best boyfriend I’ve ever had.”

“He was a great boyfriend, and he did everything correct, and he never made me feel insecure or anything like that, so it almost is harder when no one’s done anything to be mad about, and that’s hard,” she added.

source: people.com