‘Winter House’ Cast’s Dating History: Craig Conover, Ciara Miller, Luke Gulbranson and More Stars’ Love Lives

Credit: MJ Photos/Shutterstock ; Charles Sykes/Bravo ; Gregory Pace/Shutterstock

‘Winter House’ Cast’s Dating History: Craig Conover, Ciara Miller, Luke Gulbranson and More Stars’ Love Lives

Getting steamy! It may be cold in Stowe, Vermont, during the winter, but the cast of Winter House knows how to turn up the heat — and make long-lasting connections. Season 1 of Winter House, which premiered in October 2021, set the tone for vacation romances. Ciara Miller and Austen Kroll sparked up a relationship as did Andrea Denver and Paige DeSorbo. Fellow Summer House star Lindsay Hubbard also found a hookup buddy in newbie Jason Cameron. Kyle Cooke and Amanda Batula, for their part, were preparing to get married while filming the show in February 2021. The rest of the cast, which included Craig Conover and Luke Gulbranson, however, didn’t find love in Vermont — but they did have fun in the snow. When season 2 began filming in early 2022, things looked very different for the OG stars. Amanda and Kyle were married, having tied the knot in fall 2021, and Craig and Paige had connected outside of the series and begun their own relationship. “Paige and I have been dating for a little over five months now. We’re more romantic than ever,” Craig said during the October 2022 premiere of Winter House season 2. “I’m not trying to brag, but I think our friends could all use an example of a healthy relationship in the house.” [jwplayer UCVxbfB5-zhNYySv2] Amanda, for her part, exclusively told Us Weekly that she doesn’t exactly agree with Craig’s claims that he and Paige are the most functional couple in the house. “I think it’s comical,” she said in October 2022 in response to the Sewing Down South founder’s comments, noting that she thinks her husband, Kyle, “would say something similar.” She added: “I don’t know if [Paige] necessarily agrees with that [healthy label], but they are a wonderful couple and they are in a great place. Listen, if that’s the mentality he has that’s great. Keep it up, Craig.” Lindsay, meanwhile, found love with Summer House costar and longtime BFF Carl Radke after parting ways with Jason in summer 2021. Although they were just dating when they shot Winter House season 2, Carl proposed to the Hubb House PR founder in August 2022. Austen, on the other hand, found himself in hot water when he kissed Lindsay while still flirting with Ciara during an appearance on Summer House season 6, which filmed in summer 2021. He then romanced Southern Charm costar Olivia Flowers, but as of October 2022, they were no longer together. Winter House airs on Bravo Thursdays at 9 p.m. ET. Scroll down to see which Winter House stars are single — and who is off the market:

Credit: MJ Photos/Shutterstock ; Charles Sykes/Bravo ; Gregory Pace/Shutterstock

‘Winter House’ Cast’s Dating History: Craig Conover, Ciara Miller, Luke Gulbranson and More Stars’ Love Lives

Getting steamy! It may be cold in Stowe, Vermont, during the winter, but the cast of Winter House knows how to turn up the heat — and make long-lasting connections. Season 1 of Winter House, which premiered in October 2021, set the tone for vacation romances. Ciara Miller and Austen Kroll sparked up a relationship as did Andrea Denver and Paige DeSorbo. Fellow Summer House star Lindsay Hubbard also found a hookup buddy in newbie Jason Cameron. Kyle Cooke and Amanda Batula, for their part, were preparing to get married while filming the show in February 2021. The rest of the cast, which included Craig Conover and Luke Gulbranson, however, didn’t find love in Vermont — but they did have fun in the snow. When season 2 began filming in early 2022, things looked very different for the OG stars. Amanda and Kyle were married, having tied the knot in fall 2021, and Craig and Paige had connected outside of the series and begun their own relationship. “Paige and I have been dating for a little over five months now. We’re more romantic than ever,” Craig said during the October 2022 premiere of Winter House season 2. “I’m not trying to brag, but I think our friends could all use an example of a healthy relationship in the house.” [jwplayer UCVxbfB5-zhNYySv2] Amanda, for her part, exclusively told Us Weekly that she doesn’t exactly agree with Craig’s claims that he and Paige are the most functional couple in the house. “I think it’s comical,” she said in October 2022 in response to the Sewing Down South founder’s comments, noting that she thinks her husband, Kyle, “would say something similar.” She added: “I don’t know if [Paige] necessarily agrees with that [healthy label], but they are a wonderful couple and they are in a great place. Listen, if that’s the mentality he has that’s great. Keep it up, Craig.” Lindsay, meanwhile, found love with Summer House costar and longtime BFF Carl Radke after parting ways with Jason in summer 2021. Although they were just dating when they shot Winter House season 2, Carl proposed to the Hubb House PR founder in August 2022. Austen, on the other hand, found himself in hot water when he kissed Lindsay while still flirting with Ciara during an appearance on Summer House season 6, which filmed in summer 2021. He then romanced Southern Charm costar Olivia Flowers, but as of October 2022, they were no longer together. Winter House airs on Bravo Thursdays at 9 p.m. ET. Scroll down to see which Winter House stars are single — and who is off the market:

Credit: Gregory Pace/Shutterstock

Amanda Batula

The New Jersey native was invited to film Summer House season 1 after meeting Kyle that year. The twosome became official during the 2017 finale and got engaged one year later. The reality stars’ ups and downs as a couple have been featured heavily on both Summer House and Winter House. Despite a rocky road to the altar, the pair said “I do” in September 2021.

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Craig Conover

The Delaware native dated Southern Charm costar Naomie Olindo for three years before splitting in 2017. He moved on with Natalie Hegnauer in early 2020, meeting ahead of the COVID-19 quarantine shutdowns. Craig and Natalie called it quits in 2021.

That same year, Us confirmed that Craig was dating Paige. The twosome’s casual relationship played out on season 6 of Summer House, which filmed in summer 2021. During the season, which aired in early 2022, Craig confessed that he previously hooked up with Kristin Cavallari as rumors surfaced that he and Austen were in a love triangle with the Laguna Beach alum.

During season 8 of Southern Charm, which aired in summer 2022, Craig also revealed that he and ex Naomie hooked up in summer 2021 and that Paige knew all about it. The Pillow Talk author became Instagram official with the stylist in winter 2021 — and they were exclusive when they filmed Winter House season 2.

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Austen Kroll

Austen briefly dated Southern Charm costar Chelsea Meissner during season 4 of the series in 2017. He moved on with Victoria Bolyard during season 5, which aired in 2018. The beermaker had a fling with Lindsay in 2018, but he didn’t confirm it until four years later.

Madison LeCroy started dating Austen in 2018 as well. The pair dated on and off for two years before Madison exclusively told Us in December 2020 that they were done.

The TV personality was linked to Cavallari in late 2020 and rumored to be in a love triangle with her and Craig. The Hills alum, however, denied the romances in July 2021. Craig, for his part, claimed on Summer House season 6 that he had hooked up with Cavallari and Austen “hates that I was making out [with Kristin].”

While filming season 1 of Winter House in February 2021, Austen sparked a vacation romance with Ciara. When Austen visited the Hamptons that summer he was again flirty with Ciara but also made out with pal Lindsay, causing drama between the ladies. Ciara revealed during the Summer House season 6 reunion that she and Austen hooked up again but were not together.

Austen, meanwhile, was linked to Southern Charm costar Olivia in late 2021 as they filmed season 8 of the series. He exclusively told Us in May 2022 that he and Olivia were dating. While Olivia told Us in August of that year that they were still dating each other exclusively, during the season 8 reunion, which filmed in September 2022, she confirmed that had since broken up.

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Kyle Cooke

Kyle proposed to Amanda in 2018 after dating for one year. The twosome’s wedding was postponed amid COVID-19 but they finally tied the knot in September 2021. Their wedding was featured on season 6 of Summer House.

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Paige DeSorbo

After joining Summer House during season 3, which filmed in 2018, Paige had a whirlwind romance with Carl. The relationship fizzled out before the end of summer and the New York native moved on with Perry Rahbar. Although Perry briefly appeared on season 4 of the series, the duo called it quits in September 2020.

Us confirmed in October 2021 that Paige and Craig were a couple after they started seeing each other casually earlier that summer.

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Luke Gulbranson

The Minnesota native was previously engaged before he struck up romances with a few of his Summer House cast mates. Luke romanced Hannah Berner during season 4 and hooked up with Danielle Olivera in between seasons 4 and 5. When Ciara joined the cast in season 5, she revealed that she had a “history” with Luke.

During season 1 of Winter House, Luke hit on housemate Julia McGuire, but she was in a serious relationship.

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Ciara Miller

The nurse had a brief romance with Luke before joining season 5 of Summer House in 2020. During season 1 of Winter House in 2021, she started seeing Austen. The duo’s romance fizzled out due to distance that year. When Austen appeared on season 6 of Summer House in summer 2021, they found themselves in a love triangle with Lindsay as the North Carolina native flirted with both women.

Ciara revealed during the season 6 reunion, which aired in May 2022, that she and Austen had again hooked up. She vowed at the time that it was the last time.

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Jason Cameron

Jason had a major crush on season 1 Winter House costar Gabrielle Kniery, but she wasn’t feeling it, so he moved on. The model eventually started spending time with Lindsay in the house and they dated outside the show as well.

Lindsay revealed during season 6 of Summer House, which aired in January 2022, that she suffered a miscarriage during her “last couple of months” dating Jason. It isn’t clear when they broke up, but Lindsay was single while filming the Hamptons series in summer 2021.

When Jason returned to Vermont for season 2 of Winter House, which filmed in early 2022, it appeared that he had his sights set on newbie Rachel Clark, not Lindsay, who had moved on with Carl. Jason and Rachel’s vacation romance, however, didn’t last. The florist confirmed in November 2022 that she was dating someone new.

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Lindsay Hubbard

When fans met Lindsay on season 1 of Summer House she was dating Everett Weston. The duo split after one year and their breakup was revealed on season 2 of the series in 2018. Lindsay hooked up with Austen in 2018 but kept it quiet for years.

The publicist was briefly linked to costar Carl during the summer of 2019 but settled down Stephen Traversie that same year. Us confirmed in January 2021 that Lindsay and Stephen called it quits in fall 2020.

She moved on with Jason, whom she met filming Winter House in February 2021. The pair’s romance ended in summer 2021 after she suffered a miscarriage.

Lindsay sparked romance speculation with Carl again in September 2021 when they were spotted getting cozy at Amanda and Kyle’s wedding. Carl exclusively confirmed to Us in January 2022 that he and Lindsay were a couple. He proposed in August 2022.

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Andrea Denver

During season 1 of Winter House, Andrea was flirty with all the ladies, but he and Paige quickly became an item. The pair continued to casually date outside of the show — including sharing romantic moments on season 6 of Summer House, which filmed that summer. While Paige became getting more serious with Craig, Andrea realized he still had feelings for a former flame, whom he was seeing before heading to the Hamptons.

In February 2022, Andrea announced that he would not return to Winter House. Instead, he was going to focus on his relationship with model Lexi Sundin. “I didn’t feel like it was the right time for me [to leave to film the show],” he exclusively told Us in March 2022. “I reconnected with a person that really matters to me and she was my priority. I feel like it was too soon to go on vacation with my friends.”

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Rachel Clark

Rachel joined the cast of Winter House for season 2 after saving the day at Amanda and Kyle’s wedding as their last-minute florist. The New York resident quickly adapted to life on camera and sparked a romance with costar Jason while in Vermont. Despite their steamy connection, Rachel revealed in November 2022 that she was “in love” and “very happy” — with someone other than the model.

"I wasn't looking for someone 'better' than Jason, because Jason is wonderful," she told Entertainment Tonight after going public with her boyfriend, Thomas Altamirano, earlier that month. "In the end, I was just looking for something different, and I don't think there's anything wrong with that. I found my person, and I hope so much so that Jason finds his person."

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Kory Keefer

The Winter House season 2 newbie appeared to be single heading into filming in early 2022. According to previews of the new season, Kory quickly became the house flirt, telling cameras, “The girls in the house, have no idea, but I’m kinda pursuing all of them at this point.”