Southern Charm’s Austen Kroll and Craig Conover’s Friendship Ups and Downs Over the Years

Credit: Gabe Ginsberg/Getty Images

Southern Charm's Austen Kroll and Craig Conover’s Friendship Ups and Downs Over the Years

Southern Charm fans have seen many friendships come and go on the series, but when Austen Kroll joined the cast in season 4, his instant bond with Craig Conover was hard to miss. Craig quickly connected with Austen in 2016 when he started filming with the Charleston, South Carolina, residents. Unlike most of the original cast who come from Southern aristocracy, both Craig and Austen are working men. Their struggles to get their careers off the ground paired with their relationship highs and lows bonded them. However, when Austen and Craig were romantically linked to Kristin Cavallari in 2020 and 2021, respectively, drama ensued. Craig and Austen eventually moved past the love triangle incident — and have worked together on multiple business ventures — but their friendship isn’t always sound. Scroll down to see Craig and Austen's friendship ups and downs:

Credit: Gabe Ginsberg/Getty Images

Southern Charm's Austen Kroll and Craig Conover’s Friendship Ups and Downs Over the Years

Southern Charm fans have seen many friendships come and go on the series, but when Austen Kroll joined the cast in season 4, his instant bond with Craig Conover was hard to miss. Craig quickly connected with Austen in 2016 when he started filming with the Charleston, South Carolina, residents. Unlike most of the original cast who come from Southern aristocracy, both Craig and Austen are working men. Their struggles to get their careers off the ground paired with their relationship highs and lows bonded them. However, when Austen and Craig were romantically linked to Kristin Cavallari in 2020 and 2021, respectively, drama ensued. Craig and Austen eventually moved past the love triangle incident — and have worked together on multiple business ventures — but their friendship isn’t always sound. Scroll down to see Craig and Austen's friendship ups and downs:

Credit: Stewart Cook/Shutterstock

Austen Joins ‘Southern Charm’

Beermaker Austen Kroll first appeared on the Bravo series during season 4, which filmed in the summer and fall of 2016. He made his debut in April 2017 and quickly became one of Craig Conover’s closest friends.

Credit: Courtesy Craig Conover/Instagram

Trolling Craig

Austen Kroll poked fun at his pal while traveling in August 2017. “F***ing Craig on TV on the plane … ugh,” he captioned a photo of the duo on Southern Charm in flight.

Craig Conover reshared the snap, asking, “Haha do anyone's best friends ever actually say anything nice to them? #thanksgaber #southerncharm #charmedairways #youstillwatching.”

Credit: Courtesy Craig Conover/Instagram

Big Apple Adventure

“Who wants to build a *********** snowman #bestdayever,” Craig Conover wrote via Instagram in July 2019 after watching Broadway’s Frozen with Austen Kroll in New York City.

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Leaving Him Hanging

Craig Conover yelled at Austen Kroll during a season 6 episode of Southern Charm after being left alone with a group of strangers at a bar. The Sewing Down South founder called his friend out for going home early, which Austen revealed he did at the suggestion of pal Chelsea Meissner.

“I was mostly mad at him for leaving me, it was mostly for selfish reasons,” Craig confessed to Decider in July 2019. “I was mad because I needed you at the end of the night and I didn’t have anyone.”

Austen joked during their joint interview that his BFF has “separation anxiety,” which is why he freaked out when he was left alone at the bar. “I have to remind him, Craig, you’ll be fine. Just turn around and you’ll see a girl that’s looking at you and you’ll be fine,” Austen added to which Craig jokingly said, “They don’t understand me like you do.”

Credit: Courtesy Craig Conover/Instagram

Wedding Date

Craig Conover joked in January 2020 that Austen Kroll was his “plus 1” for a friend’s nuptials.

Credit: Courtesy Austen Kroll/Instagram

Cameo Crew

In May 2020, the twosome teamed up to make Mother’s Day videos on Cameo. “Whenever we do press together this is what we do, ‘Hey guys I’m Austen, and I’m Craig. And together we’re the Hardy Boys!’ I dunno I thought it was good,” Austen Kroll joked in the Instagram caption.

Credit: Courtesy Austen Kroll/Instagram

Kristin Cavallari Friendship

The duo sparked a relationship with Uncommon James founder Kristin Cavallari in the fall of 2020 while she was visiting Charleston. Craig Conover and Austen Kroll later documented their trip to Nashville when they hung out with Kristin and her BFF Justin Anderson.

“She came to town with her friend Justin and the four of us [with Craig] had dinner,” Austen exclusively told Us about their friendship in October 2020. “We’ve all been in contact ever since. We’re in this, like, big old group chat, and the group chat is active. We had a blast with them and I’m gonna take a trip to see them in Nashville sometime soon.”

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Podcast Pals

The southern gentlemen launched their “Pillows and Beer” podcast in January 2021.

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‘Southern Charm’ Season 7 Reunion Drama

Craig Conover accused Austen Kroll’s ex-girlfriend Madison LeCroy of sleeping with a “married” ex-MLB player during the cast’s February 2021 season 7 reunion. The person he was referring to was later confirmed by Madison as Alex Rodriguez, who at the time was engaged to Jennifer Lopez.

The hairstylist, however, denied to Page Six that there was anything “physical” between them.A source close to Rodriguez exclusively told Us at the time that the former athlete “never met” Madison.

After Austen opened up about his rocky relationship with the South Carolina native, whom he split from for good in December 2020, Craig had his back. “You’re a terrible person and you’re a trash can,” the lawyer said during the reunion, directing his anger at Madison.

Credit: Courtesy Austen Kroll/Instagram

Vermont or Bust

The reality stars jetted off to Vermont together to film Bravo’s Winter House in early 2021. The show aired in the fall of that year.

“It’s a little more raw,” Craig Conover told Us of the series in October 2021. “It’s a new side to us. You’re used to seeing us in suits and dressed up, and in very, like, social settings, but this will be the first time you get to see us really in a day to day.”

Austen Kroll agreed, telling Us, “It’ll be a new side of our personality … [but] that also comes with its cons, because you also get to see us in our worst moments too. But I think it should be a healthy balance.”

Credit: Courtesy Craig Conover/Instagram

Minnesota Summer

“Minnesota. Peanuts. 4th of July. America. Summer of 69,” Craig Conover captioned a series of social media photos in July 2021. The attorney celebrated the holiday weekend with his BFF Austen Kroll and Winter House costar Luke Gulbranson.

Credit: Jonathan Leibson/Polk Imaging/Shutterstock; Tommy Garcia/Bravo

Austen Approves of Paige

Craig Conover began hooking up with Winter House costar Paige DeSorbo in the summer of 2021. The twosome confirmed their romance in September of that year while attending Amanda Batula and Kyle Cooke’s wedding.

One month later, Austen Kroll commented on his pal’s relationship. "A thousand percent I see why they get along," he told E! News in October 2021. "It's something that I thought was going to happen in the house, but Craig had a girlfriend. You'll see some different things happen there. I for sure saw this happening."

Austen added: "They vibe with each other well. Like Craig is so more up her alley than other people in the house, I think. And the way the way that they laugh and banter and vibe, that's what I think makes them [work]."

Credit: Courtesy Craig Conover/Instagram

Winter Warriors

The twosome kicked off the new year with a group getaway to Aspen, Colorado, in January 2022.

Credit: ABC/WDTV

The Kristin Drama Strikes Again

Craig Conover claimed during a January 2022 episode of Summer House that he and Kristin Cavallari had a romantic relationship after previously sparking love triangle rumors involving the Hills alum and Austen Kroll in July 2021.

“I’ve hooked up with her before,” Craig told Paige DeSorbo during the episode, which filmed in July 2021. He added that Austen “hates that I was making out [with Kristin],” seemingly confirming that he and Cavallari were more than just friends at one point.

A source close to the Laguna Beach alum exclusively told Us after the episode aired that “they never hooked up,” noting that Kristin thinks the Bravo personality is “just capitalizing on her name.”

During a February 2022 episode of Summer House, Paige revealed more details about Craig's alleged text messages with Kristin about the hookup. “I guess she texted him like, ‘You are not going to make me look like an idiot with her.’ And like, ‘If you want her, like, go have her. Just don’t make me look stupid,’” Paige claimed. “And he was like, ‘OK, but you went on Instagram and lied.’ Like, ‘You can’t say you were never going to date either of us. We f***ed.'"

Credit: Stewart Cook/Shutterstock

‘Summer House’ Misstep

Craig Conover exclusively told Us in March 2022 that he stopped talking to Austen Kroll for about two months after he learned of his actions on Summer House season 6. The attorney explained that he had an issue with how the beermaker treated their pal Ciara Miller, who Austen previously dated on Winter House.

“I was just really disappointed,” the Pillow Talk: What's Wrong with My Sewing? author said at the time. “I don't watch the shows, just for my own sanity, but when I found out that he was kissing Lindsay [Hubbard] after kissing Ciara, I was just like, ‘Dude, that's literally everything that Lindsay wanted to happen.’ He just crushed Ciara. … I was just really disappointed in him.”

Craig noted that they have since mended fences. “Austen's actually in a really great place now. Since last fall, [Austen] and Paige [and] Ciara [have] been working to better themselves. So I feel bad a little bit that he has to, like, replay [all] of this now eight months later,” he told Us. “Current day we're in a great spot. Him and I are about to go on tour and we've worked through all of our issues. But it wasn't the best showing.”

Credit: Bravo

Battle Royal

Craig Conover and Austen Kroll’s tension appears to hit an all-time high during season 8 of Southern Charm. “Craig, chill the f*** out,” Austen told his friend in the May 2022 trailer for the season as the duo wrestled against a car and then onto the ground.

“Say ‘I’m sorry!’” Craig yelled at Austen after getting him into a chokehold. The reason for their fight, however, was not disclosed.

Credit: Stephanie Diani/Bravo

On Thin Ice

During the season 8 premiere, which aired in June 2022, things between Craig Conover and Austen Kroll were in a bad place after Craig claimed that Austen continually shared details about his life with other people despite their sensitive nature. “I don’t have many friends right now,” Craig told pal John Pringle, noting that he no longer trusted Austen, saying, “I don’t tell him secrets anymore.”

During Kathryn Dennis’ Great Katsby party, Austen learned that Craig had hooked up with his ex Naomie Olindo in Las Vegas despite telling the beermaker that nothing happened. Kroll took that as a slap in the face, telling cameras, “Craig is supposed to be my best friend, but this just goes to show you where Craig and my relationship has gone to.”

The friends didn’t resolve anything during the premiere and their drama spilled over into season 8, episode 2, which aired later that month. Austen was hurt by Craig's choice to hide the Naomie hookup from him, so he turned to the France native to find out what really happened in Vegas.

“You guys did not just sleep together once, true or false?” he asked Naomie, to which she replied, “Twice. That’s it.” Austen then called Craig a “good liar,” claiming he only admitted to sleeping with her once.

Credit: Courtesy Austen Kroll/Instagram

Talking It Out

The longtime friends finally made amends during season 8, episode 3, which aired in July 2022. “I’m not sure why you’re pushing me away from you,” Austen Kroll told his BFF, to which Craig Conover replied, “Sometimes I feel like you’re trying to tear me down.” The pals continued to talk out their issues, with Craig calling Austen out for making Naomie Olindo feel bad about what went down between the exes in Las Vegas.

Austen, who called himself a “major f***ing champion” of Craig, admitted that he “felt like an outsider” when he learned about the hookup from someone other than the Delaware native. Austen then confessed that it was “none of [his] business” whether Craig's current girlfriend, Paige DeSorbo, knew about the former flames hooking up. (Craig previously revealed that Paige knew everything about Naomie.)

“When you were single and you didn’t want to be alone and we hung out so much. And then you find a girlfriend and you kind of bail,” Austen claimed during the chat, to which Craig fired back, “Why would I try to hang out with someone who keeps trying to throw me under the bus?” The Pillow Talk author, however, started to back off a little bit, telling Austen that their friendship “doesn’t have to stay toxic,” adding, “I would love to rekindle this friendship.”

Credit: Todd Williamson/Bravo

Craig Says He and Austen Are an ‘Old Married Couple’

Craig Conover gave an update on Austen Kroll during an August 2023 appearance on Bleav’s “It’s Complicated” podcast. “He really struggles with self-sabotage and self-destruction,” Craig said of his pal, noting viewers will see Austen struggle with his love life once again on season 9 of Southern Charm.

“In my head I’m like, ‘You can lead a horse to water but you can’t make them drink.’ I feel like sometimes I’ve jumped on Austen’s head and held it under water, and he hasn’t drank. But he feels the same with me.”

Craig confessed that he and Austen have had “some very serious relationship problems” but they are now better communicators. “Me and Austen are like an old married couple,” he joked, noting their issues “stem from us being opposites. It’s very hard to understand each other sometimes.”

When it comes to Craig's relationship with Paige DeSorbo, he applauded Austen for being so supportive. “He respects that I’m happy. He respects the life that I’m living but it also comes from me putting in effort,” Craig said. “Both sides have to give effort to the relationship. He fortunately really respects what [Paige and I] have.”

Credit: Bravo

Craig Has Thoughts About Austen’s Season 9 Drama

When season 9 of Southern Charm premiered in September 2023, all eyes were on Austen Kroll for his rumored hookup with Shep Rose’s ex Taylor Ann Green.

Austen confirmed during a September 2023 episode that Taylor, who is BFFs with Austen's former flame Olivia Flowers, did have a “sleepover” at his house but claimed to Shep that she slept in a different room. Craig Conover, however, wasn’t convinced and voiced concerns over Austen's actions to Shep during the next episode.

“I know multiple girls that I used to date that he went and slept with after,” Craig alleged during a chat with Shep. “I found out years later.” Shep claimed that Austen had done the same thing to him, referring to former castmate Chelsea Meissner, whom Austen moved in on when Shep was away on a trip during season 4. Craig doubled down, claiming that Austen's “word doesn’t mean much when it comes to, like, hooking up with girls.”

Austen eventually confessed to Shep during an October 2023 episode that he’d lied, and he and Taylor had kissed after their respective breakups. Shep chose to forgive Austen, but Olivia was visibly upset that Taylor hadn’t told her the full truth about her relationship with Austen.

Craig, meanwhile, exclusively told Us in fall 2023 that he called out Austen both on and off camera for his shady hookup with Taylor. “I told Austen, I said, ‘I tell you everything that I say to your face this year on camera.’ Look, everyone's different. I wouldn't say that he's a bad friend to Shep. Just when my friend breaks up with someone, I stop hanging out with him,” Craig dished to Us. “But not everyone's me. … If someone did that to me, I wouldn't be friends with them anymore. But that's just me.”

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Bar Buddies

Austen Kroll and Craig Conover announced in January 2024 that they’ve teamed up with Uptown Hospitality Group to open a restaurant in Charleston called By the Way.

“Charleston has grown so much in the last few years and brought in a lot of travelers, so we wanted to create a space where locals and travelers could hang out together and enjoy the neighborhood,” Craig told Entertainment Tonight. “It’s going to be a really intimate space. We put a lot of thought into the design to try and make it as warm and inviting as possible. We’re leaning into the local, upscale, tavern vibes, so the menu is going to have elevated bar fare and approachable cocktails.” The restaurateurs opened in 2024.

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Patience Is a Virtue

“There has to be a lot of compromise and give and take,” Craig Conover exclusively told Us in September 2024 of going into business with Austen Kroll at their Charleston restaurant. “I personally just want to do business with friends.”

He confessed, “I know that I'm flying really close to the sun with that, and that's what you'll get to see this season — if we're able to make it work, because it gets scary at times. It's not just the company on the line. It's your friendship, too.”

Craig explained that after working with Austen on their “Pillows & Beer” podcast, he learned to “be patient with people” before adding restauranteur to their joint resume.

“Everyone does things differently. And I think when it comes to your personal life, that's easy to separate, you know, like, you're not responsible for each other,” he shared. “But when you bring businesses into it, and we have the podcast and we have a couple of other things, it's almost like a pressure cooker.”

Credit: Mike Marsland/Getty Images for Hayu

By The Way, We're Open!

The reality stars opened their Charleston eatery, By The Way, in December 2024. “Austen and I traveled a long time together, and we went to a lot of places around the country,” Craig Conover exclusively told Us of the vibe of the restaurant. “So we basically took our list of favorite things that we've run into in bars and put it into this place.”

He teased that the menu, which includes fried crispy oyster on a crème fraiche with caviar on top, can’t be topped in the area. Craig added that By The Way is not like any other restaurant on King Street.

“There's still a lot of people that want to have fun in their upper 20s, 30s, 40s, 50s, and this will be the spot for that,” Craig added. “I'm excited, because right now, like, I don't really have anywhere that I enjoy going out downtown again. A lot of love for all the places, but I've just kind of grown out of the nightclub scene.” (News broke that same month that Craig and Paige DeSorbo had split after three years of dating.)

Credit: Mike Marsland/Getty Images for Hayu

Finding Their Balance

“Craig is a hermit,” Austen Kroll exclusively told Us in December 2024, confessing, “I wish he had more balance in his life. I understand that his business is very important to him, but it's almost like he thinks that by hanging out [with me] that means, ‘Let's go get drunk together.’ And I'm like, ‘I don't care if you drink or don't drink.’”

He explained that he wants his longtime friend to have “more balance in his life from friends and work,” noting that fans will see their highs and lows on season 10 of Southern Charm.

Austen also admitted that he does have some “jealousy” over Craig Conover’s career accolades. “I do want people to buy my beer like that. I do. Sure. But it's not, like, a nasty jealousy,” he explained.

He noted that with Craig he feels like “people expect” him to “act a certain way,” so he cannot let loose with Austen from time to time.

Credit: Tommaso Boddi/WireImage

Season 10 Drama

During the season 10 premiere of Southern Charm, which aired in December 2024, Craig Conover and Austen Kroll had a heart-to-heart with Shep Rose over his drinking issues. (Shep blacked out at BravoCon in fall 2023, which caused tension between him and his costars.)

While the trio left the conversation as friends, Austen confessed he doesn’t “completely agree with how Craig can set boundaries, which is just a hard cut off.”

As the season continued, Austen and Craig butted heads. Austen claimed during the January 2, 2025, episode that Craig's work is the only thing he cares about. “I miss my buddy. That’s where I’m coming to you from,” Austen told Craig, claiming that if he asks him for lunch Craig always has an excuse not to come.

Austen said that when Craig “bailed on golf” with him — and instead spent his time gardening and then posted about it on social media — it felt like a “move” and that he “bailed on friendship.”

Craig revealed, “That’s what makes me happy now. Working and making money.” He argued that they were good because they see each other to do their podcast. “If you’re a real friend, you would be happy [for me],” Conover added.

Austen claimed that he is fine with Craig not drinking or going to the bar anymore, but alleged that Craig won’t even come over to his house. “I would never tell you how to live your life,” Craig yelled.

“I understand that times change,” Austen told the cameras. “I just feel like you keep those friends that you were here with as you begin to flourish, those are the friends you keep closest.”

Credit: Farreno Ferguson/Bravo

A Bahamas Breakthrough

During a March 2025 episode of Southern Charm, Austen Kroll and Craig Conover had a breakthrough after months of friction in their friendship. The costars were on a trip to the Bahamas, which was filmed in summer 2024, when Craig confided in Austen about his ongoing struggles with alcohol.

“Austen, I know that you love me. But do you have a hard time not hating me?” Craig asked while sitting at a bonfire. Austen laughed before admitting, “Sometimes, sure. I have the same thought about you, Craig.”

When asked what makes him so “mad” about Craig, Austen said he was an “embellisher.” Craig took offense, replying, “I’m a lawyer and a storyteller.”

A few minutes later, Craig pulled Austen aside to have a deeper conversation about why his recent life changes — staying in and not hanging out with Austen as often — were necessary for his health.

“I feel like where all the disconnect has come because you’ve created this wonderful image that you are terrified of disappointing someone or something that now in order to maintain this I need to sit at my house and not see me with a beer or something,” Austen told Craig.

Austen explained, “It’s like Craig doesn’t want to hang or do this because he’s got the image to protect. You’ve just gotten drunk on nice guy Craig. I just want you to loosen the reins a little bit.”

Craig confessed, “I can’t because I don’t have any lease on myself. That’s any addict. I was like, ‘F***. Me, like, trying not to be an alcoholic is now affecting my friendship with Austen.’”

Craig revealed that he was tearing up because he was “in the trenches by myself trying to better myself. Then you were like, ‘You’re never with me anymore.’ I’m like dude … ‘I can’t. I gotta stay on my couch. I leave my couch I’m going to drink a bottle of Jager and do dumb s***.’”

Austen was taken aback by Craig using the term “addict” because he’d never told him that before. Craig noted he’d “never said it out loud” but said that was his truth — he’d been trying to cut out liquor because it was taking over his world.

While Austen told the cameras that Craig's “addiction doesn’t excuse from being an a**hole,” he said it does afford Craig more “grace” on his end.

“I’m sorry that I never told you,” Craig said, apologizing for letting his recovery affect their “time together,” noting it was so he could “get better.” They ended the conversation with a hug and saying “I love you.”

Credit: Jocelyn Prescod/Bravo (2)

Literary Feud

During season 11 of Southern Charm, which premiered in fall 2025, Austen Kroll and Craig Conover got into a fight during pal Whitner Slagsvol’s literary figures party — and it plagued them throughout the season. After Austen took a jab at Craig for taking too many shots amid his newly-single era, Craig claimed Austen was “jealous” and “unhappy” in his relationship with Audrey Pratt. (Austen and Audrey split in 2025 after dating nearly two years.)

“Happy people don’t tear people down. You’re not happy,” Craig yelled at Austen, who fired back, “And here you are, tearing people down.” Craig stormed off and slammed the door as he called Austen a “f***ing loser.”

As the season continued, Craig and Austen butted heads over a variety of topics. Their feud bubbled over at Austen’s birthday dinner when Craig claimed that he hadn’t made any progress over the past few years. Austen retaliated by admitting, “I do f***ing hate you.”

Credit: Jocelyn Prescod/Bravo

At 'Peace' at Season 11 Reunion

After pushing each other’s buttons throughout season 11, Austen Kroll and Craig Conover tried to repair their friendship during the reunion, which aired in March 2026. During the sit-down, Craig addressed his blowout in Mexico, which he said was prompted by “everyone getting involved in my business” and too much drinking.

During the trip, Craig yelled at Venita Aspen for trying to “meddle” in his friendship with Austen and he also drunkenly screamed at Salley Carson to stop butting into his brief romance with Charley Manley.

“I wasn’t of right mind,” Craig confessed, while Salley pointed out he needed to “take accountability for [his] anger.”

Austen said the blowup felt like a “psychotic break,” while Madison LeCroy argued that if Craig had a “friend in that situation,” they could have helped him calm down.

“I’ve f***ing seen it so many times. … How many more times does that happen?” Austen asked after the majority of the cast told Craig his drinking wasn’t the problem and that it was his anger.

After Craig apologized to everyone, he told Austen that he thinks for now it’s a good idea to “just [be] giving each other space and hopefully try to relearn each other or accept each other for who we are.”

Austen agreed, adding that there is “some peace” in his life right now by just communicating with Craig in “group chats.” He added, “Maybe it’ll remain that way for a little bit of time.”