Paige DeSorbo and Craig Conover's Relationship Timeline Explored

Stephanie Harper - Author

Oct. 24 2023, Updated 12:19 p.m. ET

Paige DeSorbo and Craig Conover attend the 2022 MTV Movie & TV Awards: UNSCRIPTED
Source: Getty Images

There’s a reason reality TV lovers are obsessed with Paige DeSorbo and Craig Conover’s relationship. Starring in Summer House and Southern Charm, respectively, led them to film a crossover reality show. Though they first met each other years prior, it wasn't until being stuck together for 17 straight days that they really got to know each other –– and totally hit it off.

Now fans of the couple are keeping their fingers crossed that they'll be able to make it work for the long haul. Here’s the timeline of their relationship.

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February 2021 to May 2021

According to People, Paige and Craig worked together to film the first season of Winter House in February of 2021. Although rumors started swirling that April about their possible relationship, Paige denied those rumors as Craig was still dating Natalie Hegnauer at the time. In May 2021, Craig announced that he and Natalie had broken up and sources revealed that things were sparking romantically between him and Paige.

The cast of 'Winter House'
Source: Bravo

'Winter House'

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June 2021 to September 2021

Throughout the summer of 2021, Paige and Craig filmed the sixth season of Summer House and were spotted spending tons of time together. By September, they were ready to confirm the legitimacy of their relationship at Kyle Cooke and Amanda Batula's wedding. Paige later said that they "threw a[n Instagram] story up" when they were "a little drunk," but she was waiting for "the right scenery" (and possibly less booze) to truly make it Instagram official.

October 2021 to December 2021

In October 2021, Paige openly gushed about her relationship with Craig to Us Weekly. By November, the couple was comfortable enough to spend Thanksgiving together with Craig's family. That December, they finally went Instagram feed official when Paige shared a PDA-filled pic from the Southern Charm Season 8 wrap party. "Sew in love," she wrote, clearly making a pun on Craig's pillow collection.

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January 2022 to March 2022

Details about the start of Paige and Craig's relationship came to light in January 2022. She told Entertainment Tonight about a temporary love triangle she was wrapped up in with Craig and her Winter House fling Andrea Denver.

"Craig was not the reason I stopped hanging out with Andrea," she said. "I was no one's girlfriend [at the time], so I was very much in the mentality of, I don't really owe any of these guys any explanation for my decisions ... I definitely was playing the field all spring and certainly all summer."

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Obviously, the drama didn't put a stop to Paige and Criag's relationship, as they clearly continued to move forward in a positive way.

In February 2022, Craig opened up about the relationship, saying, "We are each other’s biggest fans ... I think I’m always rooting for her, she’s always rooting for me, which honestly goes really far in a relationship."

They further solidified their couple status by co-hosting a live Valentine's Day shopping event on Instagram and walking the red carpet at the Sports Illustrated Super Bowl Party.

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April 2022 to June 2022

In April 2022, Craig revealed to Bravo that he'd be receiving input from Paige about future renovations to his home — which is a pretty serious request in any relationship. The couple made a public appearance at the MTV Movie and TV Awards: Unscripted on June 5, 2022. They spent the evening arm-in-arm with smiles on their faces, and also shared sweet snaps from their hotel stay in L.A.

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July 2022 to December 2022

In summer 2022, Paige and Craig went on with their long-distance relationship (Paige in NYC, Craig in Charleston) while continuing to answer questions from the media about a possible upcoming engagement and wedding, and where they would settle down together in the future. Craig told E! in October 2022 that the plan was for them to one day raise a family together in Charleston.

The two maintained that they were working toward an engagement when they were ready. And as the year wrapped up, the couple took a trip to Paige's hometown of Albany, N.Y.

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January 2023 to August 2023

In early 2023, Paige admitted to People that long distance had its challenges, but that she felt "zero pressure" to move to Charleston yet. "Craig needs to live in New York. He needs a little Northeast class," she joked to the outlet that February. "New York really is and will always be the best." Paige also admitted in a May 2023 episode of Summer House that her independence (and her not being ready for an engagement yet) made Craig feel insecure.

In June 2023, the two took a beautiful Italian vacation together. And in August 2023, Paige opened up about her ongoing project in which she took the lead in redesigning the interior of Craig's Charleston home, giving it a more "preppy" vibe.

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September 2023 to October 2023

In September 2023, Taylor Ann Green accused Paige during the Season 9 Southern Charm premiere of being unfaithful to Craig. But Craig maintained that the tumor was false, telling E! that month: "It was just sad for me because I think I realized in that moment how lost Taylor really is/ I care about her and I was like, ‘Man, you're really struggling."

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He later added: "To say that about Paige — my reaction, the reason I walked away was because there was nothing I could do to help her in that moment. I kinda laughed because I was like, 'Me and Paige just sit on her couch and watch TV.' It would be a little hard for either of us to be out there being secretive. I don't think that comes with this territory anymore."

In October 2023, Craig appeared on Watch What Happens Live and was asked about whether Paige was moving to Charleston or Craig was moving to New York. Craig said that he would be "down" for moving to the Big Apple and would "make it work."

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