What was Craig Conover’s first DM to Paige DeSorbo? Bravo stars’ relationship timeline explored

Recently, Bravo’s Winter House star Paige DeSorbo revealed in the E! News’ series Down in the DMs that she had chatted with her boyfriend Craig Conover long before the couple met in Summer House Season 4.

Craig had DMed Paige DeSorbo regarding a painting of her that had been made by someone else. Speaking about the message, Paige said,

"Craig actually DMed me off of a painting that I posted that somebody painted of me, and he said, "Wow, this is really cool" and I said, "LOL, I know, right?"

She said that they did not message each other again for two years and remarked,

"So, I don't know if I nailed it with that response, or that was awful."

Paige also revealed that Craig and her primary source of communication on social media was sending "memes and videos back and forth to each other."

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Paige DeSorbo and Craig Conover’s relationship timeline explored

After chatting with each other on Instagram, Paige DeSorbo and Craig Conover met for the first time in the summer of 2019 while shooting for Bravo’s Summer House Season 4. The Southern Charm cast, including Craig, appeared on an episode of the show to attend Kyle Cooke’s summer party.

It wasn’t until February 2021 that the couple finally got a chance to get to know each other as Winter House Season 1 co-stars. During the show's shooting, the cast spent 17 days together in total, and Paige DeSorbo flirted heavily with Andrea Denver. Conover was already in a relationship with Hegnauer at the time.

After filming the show, Paige DeSorbo went on a trip with her friends to Charleston, which is Craig’s hometown. Fans speculated at the time that she had gone to visit Craig, but she denied it on the podcast, Not Skinny But Not Fat, in April 2021 by saying,

"Craig and I are a thousand percent not dating. 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."

Paige DeSorbo later confessed in an interview with ET Online that she and Conover shared their first kiss during the trip and moved a little bit out of the friend zone. She said,

"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. 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."

Paige DeSorbo started filming for Summer House Season 6 in June of 2021, and fans speculated that Craig might accompany her on the show. The duo went to the PGA Tour's FedExCup Playoffs together in August 2021 but had not revealed their relationship status to anyone. They also attended Kyle Cooke and Amanda Batula’s wedding in September 2021.

Paige DeSorbo and Craig Conover officially announced their relationship in October of 2021. Craig told at the time,

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

He revealed that their relationship was formed based on friendship. A month after the announcement, Paige told on the Call Her Daddy podcast that she was angry at people who thought their relationship was a “PR stunt.”

The same month, the couple revealed in an interview with Daily Pop that they would be spending the holidays with each other's families. Paige celebrated Thanksgiving holidays with Craig’s family in Delaware, and Conover celebrated Thanksgiving with his girlfriend’s family.

DeSorbo made her relationship with Conover Instagram official in December 2021 by posting a photo of the two together at a holiday event.

Throughout Season 6 of Summer House, fans saw Paige DeSorbo and Craig Conover’s relationship grow in the early stages when they had not even defined their relationship. During the shooting, Hubbard told Paige that Conover was sleeping with Kristin Cavallari. Both later denied the accusations.

Paige also sent her boyfriend flowers in March 2022 when Conover released his book Pillow Talk: What's Wrong with My Sewing?

Craig told Bravo in an interview that Paige would live with him in Charleston for the summer after being in a long-distance relationship for so long.