Winter House: Everything We Know About Paige & Craig’s Relationship

Fans of both Summer House and Southern Charm were elated when Bravo created a spinoff of the two called Winter House. It was a house where two worlds collided and viewers couldn’t get enough. Although Craig Conover (Southern Charm) and Paige DeSorbo (Summer House) were in relationships with other people on Winter House and their respective shows, something changed at the end.

The last glimpse of Winter House showed Paige and Craig kissing in a shocking twist. The two kept a low profile after filming but were caught visiting each other in the summer of 2021. It wasn’t until recently that they finally admitted to their fans that they were exclusive.

The Duo Met Before Winter House…

Before Winter House released, Bravo fans had to know what the spinoff would be like. In reality, it was Summer House with a few new additions in a different, snowy environment. Craig entered the house in a relationship with his girlfriend from Charleston, Natalie, and Paige was head over heels for a fellow cast member, Andrea Denver. There was no hint of a possible romance between these two, yet they were very comfortable with each other.

According to Distractify, Paige said that the two had met each other three years before filming. At the time, Craig was single but Paige was in a relationship. So, when Paige heard that Craig was going to be in the house with her, she was hoping things would be different but alas — he was the one in the relationship that time around.

…And Craig Had A Crush On Her

Not only did Paige admit that she had a crush on Craig when she first met him, but Craig also had a crush on Paige without her realizing it. In a confessional, Craig told the cameras that he always had a crush on Paige but the timing never worked because one of them was always in a relationship.

In Craig’s respective reality show, Southern Charm, some of his more dramatic moments were when he was in a long-term relationship with Naomie Olindo. The two eventually broke up and moved on, so fans were hoping that Craig would finally be with someone he could be happy with.

It’s Instagram Official!

After a summer of speculation, Craig and Paige confirmed they were dating in September when they were at Kyle and Amanda’s wedding from Summer House. Paige is an influencer with a strong dedication to aesthetics on her Instagram, so fans were stunned when she interrupted her fashion moments for a snippet of her and Craig!

According to News Break, the photo was snapped at Southern Charm’s season 8 finale party. Bravo fans have been waiting for the newest season of Southern Charm to see how it compares to previous seasons. Paige captured the image “Sew in love.”

Paige Was Happy Craig Had A Girlfriend On Winter House

If Summer House fans love the dynamic of the show, they would love Winter House. Winter House introduced familiar faces to the Bravo world and placed them all under one roof. With so many singletons, many weren’t looking to find love on the show, but it looks like Paige and Craig unintentionally did.

According to US Weekly, Paige was happy Craig was in a relationship when they entered the house. “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,” she said.

Long Distance Works For Them

One of the biggest issues a few of the castmates had was that if they continued a relationship outside of the winter house, they’d have to embark on a long-distance relationship. Southern Charm’s Austen Kroll and Summer House’s Ciara Miller didn’t work out for that exact reason, but it looks like long distance is working for Paige and Craig.

Craig remains in Charleston and Paige still lives in New York City, but distance has made the pair more “present,” according to Paige. In an interview for US Weekly, she said, “We actually love long-distance. We’re two people that are very independent and have so much going on during the week.” She continued saying that she flies to Charleston on the weekends and the two are more present because they finish work on the weekdays.

Paige & Craig Teamed Up For Sewing Down South’s Charities

Craig is one of the more likable cast members on Southen Charm. He’s had his moments over the years but he slowly grew into the independent businessman he always dreamt of becoming. Not only did he start his own law firm but he also has his own home decor business, Sewing Down South.

In early December, Craig held a fundraiser to support Breast Cancer awareness for a local cancer center by selling his Nice Guy merchandise. In the picture posted on Instagram, Paige was beside him wearing one of his hats, proving that they work well together.

They’re Now Both A Part Of Each Other’s Shows

The sixth season of Summer House is coming soon and Craig is shown throughout the trailer with Paige. In it, Paige and Craig are new in their relationship and seeing where it takes them. However, there looks to be trouble in paradise when Paige brings up rumors about his fling with another celebrity and Andrea still has feelings for Paige. It would be a huge twist if Craig joined the show because this would make them one of the best Summer House couples.

Likewise, after Paige posted a photo of her at Southern Charm‘s wrap party, it appears like she’ll be making a few appearances throughout that series as well.

Number 1 Fans

Until viewers get to see season 6 of Summer House and season 8 of Southern Charm, they’ll never know how Paige and Craig work as a couple. But according to Paige, the pair are each other’s biggest fans.

According to US Weekly, Paige said how happy she and Craig were. “I don’t think either of us has ever dated someone else in the industry. We get each other, it’s nice. We really are each other’s biggest fans, which is something that I’ve always looked for,” she said.

They’re Spending The Holidays Together

Summer House and Southern Charm are alike in the fact that it shows a group of friends hanging out and going through the ups and downs of life together, but Southern Charm focuses more on life lessons and the differences of growing up in the South.

Craig moved to Charleston from his native Delaware, which is how he got on the show. Meanwhile, Paige moved to New York City while her family is still in Albany. Despite their different hometowns, the two are spending the holiday season together. According to Bravo, they did Thanksgiving with both of their families. It’s not known where the couple will spend Christmas but it looks promising!

Paige Jokes About An Upcoming Engagement

It’s been said that they two started dating in May 2021 but an official timeline is unknown. Considering the two have met each other’s families, are enjoying long distance, and are a part of each other’s shows, their relationship seems stronger than most couples who met on reality TV. They’re so strong that Paige even joked about a possible engagement.

While talking to E! News, Paige was asked if they were “heading towards a potential engagement,” to which she replied, “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!” If an unexpected engagement does happen, Bravo fans will cry with happiness for the ultimate couple.

About The Author

Lynn Gibbs
(1645 Articles Published)

Lynn is a nomad who travels the globe on the hunt for her next adventure with her husband. A lover of being outside (and finding the best latte in town), Lynn is typically hiking, walking, or jogging when she’s not focusing on her love of writing. When it comes to shows streaming on Netflix or anything Bravo-related, Lynn’s your gal.

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