Bravo Stars Paige DeSorbo & Craig Conover’s Complete Relationship Timeline

The two had a crush on each other for years before they started dating.

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Bravo stars Paige DeSorbo and Craig Conover
(Alberto E. Rodriguez/Getty Images Entertainment/Getty Images)/(Paul Morigi/Getty Images Entertainment/Getty Images)

When the casts of Summer House and Southern Charm shacked up for Winter House last year, Craig Conover and Paige DeSorbo were both focused on other people. Craig was dating former TV personality Natalie Hegnauer, while Paige was busy hitting it off with Bravo newcomer Andrea Denver. They’d been friends for years — and had mutual crushes on each other — but the timing just never worked out. Now, however, the two have been together for several months and things appear to be going exceptionally well.

“We’ve had such a great six months already,” DeSorbo told Entertainment Tonight in January 2022. “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.” According to the fashion writer, she and Conover have even discussed getting married someday. “It’s a normal conversation, but there’s nothing very serious happening,” she said.

So how did the couple go from dating other people to talking about tying the knot in just six months? Check out the reality stars’ complete relationship timeline.

February 2021

Conover and DeSorbo headed to Vermont to film Season 1 of Winter House in early 2021. They were joined by fellow Bravo stars Kyle Cooke, Amanda Batula, Lindsay Hubbard, Luke Gulbranson, Ciara Miller, Austen Kroll, Andrea Denver, Julia McGuire, Gabrielle Kniery, and Jason Cameron.

April 2021

After filming, speculation began to swirl about Conover and DeSorbo’s relationship status. DeSorbo put the rumors to rest on the Not Skinny But Not Fat podcast in April, two months after filming for Winter House wrapped. “Craig and I are a thousand percent not dating,” she said, according to Us Weekly. “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.”

That same month, Conover confirmed that he was still dating Hegnauer. “Well, there’s a lot that happens in Winter House, but no, I’m still with my girlfriend, Natalie, here in Charleston,” the lawyer told Us Weekly. Alas, their relationship didn’t last much longer.

May 2021

Conover announced that he was single on the Pillows and Beer podcast, which he hosts with his Southern Charm co-star Austen Kroll. “I’m going through, like, [a] break up, and it’s nothing terrible, it’s just so easy to drink to avoid dealing with anything,” he revealed.

August 2021

Filming for Summer House Season 6 began in August 2021, and Conover was reportedly spotted at the Hamptons house on multiple occasions. The next month, he and DeSorbo attended the PGA Tour’s “FedExCup Playoffs” at the Liberty National Golf Course. One source told Page Six that the two were “good friends and not dating,” while another said that Conover “was very excited to be there with Paige.”

September 2021

The pair confirmed their relationship in September by sharing a steamy photobooth picture from Batula and Cooke’s wedding on Instagram. “We did get a little drunk at the wedding and threw a Story up there from the photo booth,” DeSorbo told Us the following month. “[But] I’m just waiting [for] the right scenery to happen to snap [an official] pic.”

October 2021

DeSorbo opened up about their relationship in an interview with Us in October. “I met Craig, actually, three years ago and he was single,” she said. “I had a boyfriend and I absolutely respected that I was in a relationship.” Ultimately, things didn’t work out between her and her ex, Perry Rahbar, so she was excited to film Winter House and see if something could be there with Conover.

“When we got to Vermont, I didn’t know he had a girlfriend. So, I was a little bummed when I first got there. But, of course, he was absolutely respectful to his girlfriend,” she said. “And I’m so happy now looking back that he had a girlfriend because we built just a very platonic friendship, which is, like, the base of our relationship now. Everything really does happen for a reason.”

Instagram/Craig Conover

“It sounds so cliché, but Craig just gets me,” DeSorbo continued. “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.” Conover agrees. “I don’t think either of us has ever dated someone else in the industry,” he said. “We get each other, it’s nice. We really are each other’s biggest fans, which is something that I’ve always looked for.”

November 2021

After celebrating Thanksgiving with each other’s respective families, DeSorbo made it clear that she wouldn’t say no if Conover popped the question. “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!” she said when asked about the possibility of getting engaged on E!’s Daily Pop.

December 2021

DeSorbo and Conover made it Instagram official in December. “Sew in love,” DeSorbo wrote alongside a photo of her and Conover, referencing his sewing brand, Sewing Down South.

January 2022

According to Us Weekly, Bravo fans will see more of DeSorbo and Conover’s love story on Summer House — and it’ll probably get a little messy. In January, DeSorbo told Entertainment Tonight that she was balancing two guys while filming last summer. “Craig was not the reason I stopped hanging out with Andrea,” she said. “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.”

Eventually, though, it became clear that Conover was the man she wanted to be with. “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 explained. “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.”

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