Winter House’s Lindsay Hubbard and Austen Kroll’s Relationship Ups and Downs

Credit: Zack DeZon/Bravo (2)

Winter House’s Lindsay Hubbard and Austen Kroll's Relationship Ups and Downs

A crossover connection! As fans prepared for a Bravo multiverse event with the premiere of Winter House, cast members Lindsay Hubbard and Austen Kroll shocked viewers when they opened up about their history. Ahead of Lindsay's entrance on the Summer House spin off series, she talked about getting to film with Austen after being friends for years. “I haven't seen him in over a year when we started filming, so that was the longest I've gone since I’ve met him,” the publicist exclusively explained to Us Weekly in October 2021. “So I went into it like, ‘Hey, I'm just so f—king excited to, like, see my best friend.’ And we talk every day — sometimes breakfast, lunch and dinner, you know, sometimes we will go a couple of days without talking, but we're always on the phone. … Austen and I do have a history when we're both single that you don't know what's going to happen.” Although Lindsay was ready to see where their time in Vermont would take them, the Southern Charm star already had his sights set on Ciara Miller before Lindsay arrived. As episodes of Winter House continued to air, the costars faced some tension in their relationship following an embarrassing segment on Watch What Happens Live With Andy Cohen. During an October 27 appearance on the late night talk show, things took a turn when Austen chose Ciara for most of the romantic questions in a game of "Pick Your Winter Spouse!, as Lindsay watched on in the audience. After the episode aired, the New York native admitted that she struggled to keep up "a happy face" while she was actually "crying inside." "You never know what kind of questions or quizzes are going to be asked. I was definitely taken aback at the responses that Austen gave," she said during a November 2021 episode of the "Reality Life with Kate Casey" podcast. "I think he could have been a little bit more respectful to me and to our friendship. We've had conversations about that in the past. Specifically, after Winter House filming, I had a conversation with him about that." [jwplayer GjWOjB1H-zhNYySv2] After fans noticed that the twosome seemingly unfollowed one another, Austen revealed that she actually blocked him. The Summer House star also confirmed that she was hitting pause when it came to Austen. "I can't be [OK] with keeping that kind of person in my life. Like, I spend so much time caring and nurturing for my friendships and being the best friend I can be to everyone around me," she noted at the time. "If it's not going to be reciprocated [after] almost four years of friendship and if it's still not there, then I don't need to train a 34-year-old man how to be a good friend to me." Austen, for his part, thought they had reached a place of understanding. “I thought that we were moving on and being, like, much more adult about it to be totally honest,” he said during a “Pillows and Beer” livestream with Craig Conover the day Lindsay's "break" comments made headlines. Amid issues in her friendship with the Kings Calling Brewing Co. founder, Lindsay also sparked romance rumors with her costar Carl Radke. As rumors swirled about the status of their relationship, following a past fling between the longtime friends, Lindsay got honest about how Carl was an important fixture in her life. “We’ve been super close, we've been best friends, we started the show together. Not having him at Winter House was very strange for me. I mean, he was helping me pack the night before I left,” she told Us in October. “I FaceTimed him a bunch while I was there and we hang out all the time, we live in the same building in New York and we're just, like, really, really close.” Lindsay also joked about being linked to several Bravo costars at once. “Here I am, like, on Winter House talking about Austen and how I’m in love with him, but, you know, I’m also in love with Carl, Kyle [Cooke] and Amanda [Batula],” she shared with Us. “Carl and I, you know, he's been going through a very different lifestyle phase and change of his life. I've been very supportive of him since day one.” Winter House airs on Bravo Wednesdays at 9 p.m. ET. Scroll on for all the ups and downs between Lindsay and Austen:

Credit: Zack DeZon/Bravo (2)

Winter House’s Lindsay Hubbard and Austen Kroll's Relationship Ups and Downs

A crossover connection! As fans prepared for a Bravo multiverse event with the premiere of Winter House, cast members Lindsay Hubbard and Austen Kroll shocked viewers when they opened up about their history. Ahead of Lindsay's entrance on the Summer House spin off series, she talked about getting to film with Austen after being friends for years. “I haven't seen him in over a year when we started filming, so that was the longest I've gone since I’ve met him,” the publicist exclusively explained to Us Weekly in October 2021. “So I went into it like, ‘Hey, I'm just so f—king excited to, like, see my best friend.’ And we talk every day — sometimes breakfast, lunch and dinner, you know, sometimes we will go a couple of days without talking, but we're always on the phone. … Austen and I do have a history when we're both single that you don't know what's going to happen.” Although Lindsay was ready to see where their time in Vermont would take them, the Southern Charm star already had his sights set on Ciara Miller before Lindsay arrived. As episodes of Winter House continued to air, the costars faced some tension in their relationship following an embarrassing segment on Watch What Happens Live With Andy Cohen. During an October 27 appearance on the late night talk show, things took a turn when Austen chose Ciara for most of the romantic questions in a game of "Pick Your Winter Spouse!, as Lindsay watched on in the audience. After the episode aired, the New York native admitted that she struggled to keep up "a happy face" while she was actually "crying inside." "You never know what kind of questions or quizzes are going to be asked. I was definitely taken aback at the responses that Austen gave," she said during a November 2021 episode of the "Reality Life with Kate Casey" podcast. "I think he could have been a little bit more respectful to me and to our friendship. We've had conversations about that in the past. Specifically, after Winter House filming, I had a conversation with him about that." [jwplayer GjWOjB1H-zhNYySv2] After fans noticed that the twosome seemingly unfollowed one another, Austen revealed that she actually blocked him. The Summer House star also confirmed that she was hitting pause when it came to Austen. "I can't be [OK] with keeping that kind of person in my life. Like, I spend so much time caring and nurturing for my friendships and being the best friend I can be to everyone around me," she noted at the time. "If it's not going to be reciprocated [after] almost four years of friendship and if it's still not there, then I don't need to train a 34-year-old man how to be a good friend to me." Austen, for his part, thought they had reached a place of understanding. “I thought that we were moving on and being, like, much more adult about it to be totally honest,” he said during a “Pillows and Beer” livestream with Craig Conover the day Lindsay's "break" comments made headlines. Amid issues in her friendship with the Kings Calling Brewing Co. founder, Lindsay also sparked romance rumors with her costar Carl Radke. As rumors swirled about the status of their relationship, following a past fling between the longtime friends, Lindsay got honest about how Carl was an important fixture in her life. “We’ve been super close, we've been best friends, we started the show together. Not having him at Winter House was very strange for me. I mean, he was helping me pack the night before I left,” she told Us in October. “I FaceTimed him a bunch while I was there and we hang out all the time, we live in the same building in New York and we're just, like, really, really close.” Lindsay also joked about being linked to several Bravo costars at once. “Here I am, like, on Winter House talking about Austen and how I’m in love with him, but, you know, I’m also in love with Carl, Kyle [Cooke] and Amanda [Batula],” she shared with Us. “Carl and I, you know, he's been going through a very different lifestyle phase and change of his life. I've been very supportive of him since day one.” Winter House airs on Bravo Wednesdays at 9 p.m. ET. Scroll on for all the ups and downs between Lindsay and Austen:

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A Secret Past

Lindsay and Austen both hinted that their past was more than just platonic, with the former salesman revealing on a “Pillows and Beer” livestream they had a hookup “four years ago." He also discussed the 2018 fling with Ciara on the show, saying, "When that happened, in my opinion, we moved on."

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That Bravo Bond

Ahead of the Winter House premiere, Lindsay explained to Us why she didn't open up about her connection with Austen in an attempt to "protect" their friendship.

“We're living in a very different environment than most people and you need as many friends as you can to just bounce ideas off and try to work through certain situations,” she noted to Us in October 2021. “If you can find that person in somebody else on a different show who understands what you're going through, but it's not too close to the situation, that's where we became friends and we've been nurturing that friendship for the last three years. [Fans will] start to see that development, that friendship. I know it feels like it came out of nowhere, it really does, [but] it really has not come out of nowhere. We do have a history of friendship and physical history of romance.”

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Drunken Declaration

During the second episode of Winter House, Lindsay got drunk and decided to lay it all out on the table for Austen.

“I am in love with you,” she told Austen. “I’m in love with you. I don’t think you understand.”

The Maryland native, who had already hooked up with Ciara before Lindsay got there, replied, “I don’t think I still do. Are you just saying this because you’re drunk right now?”

Prior to the episode airing, Lindsay admitted that she was "too drunk” during the heated conversation.

“I come in and start some s—t, and like, tell everyone I’m in love with them and I’m not. And I’m, like, wasted while doing it and you’re just, like, ‘No, why? No! Brush your hair. F—k, No I can’t,’” she told Us. “In that moment, I did say that I was in love with a lot of people — I haven’t seen the episode and whether they play all of those people or not, I have no idea.”

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The Friend Zone

Following Lindsay's confession the night before, Austen took her aside the next morning to explain that it wasn't going to work out romantically for them.

"I didn't know that. Linds, I love you — like a sister," he noted. "It just works so much better this way. I don't want this to f--k up because we are too close."

The duo discussed the moment further during an appearance on WWHL, when Lindsay hinted that Austen suggested making their relationship official on New Year's Eve in January 2021, which she previously discussed with costar Julia McGuire on Winter House.

Austen, for his part, responded on WWHL, saying, "Oh, I mean, if you don't tell your best friend from time to time, you're like, 'I'm sick of everything. Wouldn't it just be so much easier if you and I dated?'"

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That Awkward 'WWHL' Appearance

During the same October 2021 appearance on WWHL, Austen played a game titled "Pick Your Winter Spouse!" where he had to choose between Lindsay or Ciara Miller in various scenarios.

Austen ended up picking Ciara as the better cuddler and better kisser, which was awkward with Lindsay listening in the audience. Shortly after the interview, fans noticed that the pair were no longer following one another on Instagram.  

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The Aftermath

Lindsay addressed the tense situation less than one week later.

“I don't think I've ever been in more of an awkward uncomfortable situation in my entire life," she said during an appearance on the "Reality Life with Kate Casey" podcast in November 2021. "I'm just always a very comfortable in my own skin kind of person. But that moment was extremely uncomfortable and listen, thank God [Austen's sister] Katie [Kroll] was there because I was holding her hand, like, the world was coming to an end."

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His Side of the Story

That same day, the Charleston resident explained that he thought there were no plans for him and Lindsay to explore that “romantic side” of their relationship.

“The tea on Watch What Happens Live is she ended up, like, you know, blocking me,” he noted on the “Pillows and Beer” livestream in November 2021.

Ciara also weighed in on the situation when she questioned why Lindsay took the game so seriously.

"I don't understand what he did. What did he do wrong? If he answered the question honestly, I don't feel like there's an issue in that," the Georgia native said during an appearance on WWHL in November 2021. "Even if Austen would have went towards Lindsay [when he answered the questions], if he would have chose Lindsay, cool. Who cares?"

Ciara added that the drama shouldn't be "that serious," saying, "It's a game and, like, sorry I'm the better kisser."

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Lindsay Gets Her Revenge

Lindsay turned the tables on Austen when she participated in WWHL’s “Activate the Mate” during a November 2021 appearance. During the game, the TV personality had to choose between Austen and Jason Cameron — and Lindsay didn’t go easy on the Southern Charm star.

When asked who has bigger BDE, who can bench press more and who is the better cuddler and kisser, Lindsay picked Jason, whom she has a connection with on Winter House, for every answer. She also noted that Jason has his life together, hinting that Austen does not.

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A Future Reconciliation?

“This is not the first time Austen and I have gotten into any sort of tiff,” Lindsay exclusively told Us Weekly in December 2021. “That's what happens when you have a close friendship with somebody when you're very, very close — and you're best friends or you consider yourselves best friends — you’re bound to get into some sort of fight. It's just, unfortunately, this one was very public. So yeah, I don't think that our friendship is over. I think it will repair, [but] it might not look the same as it did before.”

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Making Amends

"I was in Charleston with the Loverboy team in December [2021] and I ran into him. Obviously, my priorities have changed and I was busy with Loverboy and Austen was filming the [Southern Charm] finale. We kind of talked but we agreed that we need to have a bigger conversation," Lindsay shared during an appearance on WWHL in January 2022. "That hasn't happened yet, but I am sure it will."

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Bringing Up the Past

In March 2022, Austen responded to an Instagram user who called Carl an upgrade for Lindsay compared to him, writing, "Lmao that would imply that I was ever an option."

He added: "Once again. Lmao. Got told she was in love with me, I said no thanks!"

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Back to Talking

“I did speak to Austen recently and we talked,” Lindsay exclusively told Us Weekly in April 2022.

The publicist teased that she and Austen will hash out their drama surrounding his WWHL comments during the Summer House season 6 reunion. She also hinted that the love triangle between her, Austen and Ciara, which transpired during summer 2021, would be discussed.

“I wouldn’t say it’s explosive. It was interesting,” Linsday told Us of the reunion. “I think that some people take accountability and others do not. It was, like, the classic, lay into Lindsay situation, which is unfortunate to see because you can’t blame me for everything in life.”