Southern Charm’s Austen Kroll, Craig Conover’s Ups and Downs

‘Southern Charm’ stars Austen Kroll and Craig Conover’s friendship has captivated audiences since 2017 — relive their friendship highs and lows

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.

Conover quickly connected with Kroll in 2016 when he started filming with the Charleston, South Carolina, residents. Unlike most of the original cast who come from Southern aristocracy, both Conover and Kroll are working men.

Their struggles to get their careers off the ground paired with their relationship highs and lows bonded them. However, when Kroll and Conover were romantically linked to Kristin Cavallari in 2020 and 2021, respectively, drama ensued.

While Cavallari denied being in a love triangle in July 2021, Conover claimed during a January 2022 Summer House episode that he had “hooked up with her before.” He later alleged Kroll got jealous over the fling, telling Paige DeSorbo on the show that Kroll “hates that I was making out [with Kristin].” Conover and Kroll have seemingly moved past the drama — and have been cohosting their “Pillows and Beer” podcast since 2020.

Scroll down to see Conover and Kroll’s friendship ups and downs:

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. Conover quickly connected with Kroll in 2016 when he started filming with the Charleston, South Carolina, residents. Unlike most of the original cast who come from Southern aristocracy, both Conover and Kroll are working men. Their struggles to get their careers off the ground paired with their relationship highs and lows bonded them. However, when Kroll and Conover were romantically linked to Kristin Cavallari in 2020 and 2021, respectively, drama ensued. While Cavallari denied being in a love triangle in July 2021, Conover claimed during a January 2022 Summer House episode that he had “hooked up with her before.” He later alleged Kroll got jealous over the fling, telling Paige DeSorbo on the show that Kroll “hates that I was making out [with Kristin].” Conover and Kroll have seemingly moved past the drama — and have been cohosting their “Pillows and Beer” podcast since 2020. Scroll down to see Conover and Kroll’s friendship ups and downs:

Credit: Shutterstock (2)

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. Conover quickly connected with Kroll in 2016 when he started filming with the Charleston, South Carolina, residents. Unlike most of the original cast who come from Southern aristocracy, both Conover and Kroll are working men. Their struggles to get their careers off the ground paired with their relationship highs and lows bonded them. However, when Kroll and Conover were romantically linked to Kristin Cavallari in 2020 and 2021, respectively, drama ensued. While Cavallari denied being in a love triangle in July 2021, Conover claimed during a January 2022 Summer House episode that he had “hooked up with her before.” He later alleged Kroll got jealous over the fling, telling Paige DeSorbo on the show that Kroll “hates that I was making out [with Kristin].” Conover and Kroll have seemingly moved past the drama — and have been cohosting their “Pillows and Beer” podcast since 2020. Scroll down to see Conover and Kroll’s friendship ups and downs:

Credit: Stewart Cook/Shutterstock

Austen Joins ‘Southern Charm’

The beermaker 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 Conover’s closest friends.

Credit: Courtesy Craig Conover/Instagram

Trolling Craig

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

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

Credit: Courtesy Austen Kroll/Instagram

Christmas Cool

“Craig is definitely on Santa’s s–t list this year. #noshavenovemberforkris,” Kroll joked via Instagram in December 2017.

Credit: Courtesy Craig Conover/Instagram

Big Apple Adventure

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

Credit: Shutterstock (2)

Leaving Him Hanging

Conover yells at 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 calls his friend out for going home early, which Kroll 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,” Conover 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.”

Kroll 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,” Kroll added to which Conover jokingly said, “They don’t understand me like you do.”

Credit: Courtesy Craig Conover/Instagram

Wedding Date

Conover joked in January 2020 that 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,” Kroll joked in the Instagram caption.

Credit: Courtesy Austen Kroll/Instagram

Kristin Cavallari Friendship

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

“She came to town with her friend Justin and the four of us [with Craig] had dinner,” Kroll 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.”

Credit: YouTube

Podcast Pals

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

Credit: John Valkos/Tommy Garcia/Bravo

‘Southern Charm’ Season 7 Reunion Drama

Conover accused Kroll’s ex-girlfriend 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 LeCroy 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” LeCroy.

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

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,” 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.”

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,” Conover captioned a series of social media photos in July 2021. The attorney celebrated the holiday weekend with his BFF and Winter House costar Luke Gulbranson.

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

Austen Approves of Paige

Conover began hooking up with Winter House costar 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, 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.”

Kroll 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

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

“I’ve hooked up with her before,” Conover told DeSorbo during the episode, which filmed in July 2021. He added that Kroll “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 Cavallari thinks the Bravo personality is “just capitalizing on her name.”

During a February 2022 episode of Summer House, DeSorbo revealed more details about Conover’s alleged text messages with Cavallari 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,’” DeSorbo 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—ked.'”

Credit: Stewart Cook/Shutterstock

‘Summer House’ Misstep

Conover exclusively told Us in March 2022 that he stopped talking to 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 Kroll 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.”

Conover 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

Conover and Kroll’s tension appears to hit an all-time high during season 8 of Southern Charm. “Craig, chill the f—k out,” Kroll 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!’” Conover yelled at Kroll 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 Conover and Kroll were in a bad place after the attorney claimed that Kroll continually shared details about his life with other people despite their sensitive nature. “I don’t have many friends right now,” Conover told pal John Pringle, noting that he no longer trusted Kroll, saying, “I don’t tell him secrets anymore.”

During Kathryn Dennis’ Great Katsby party, Kroll learned that Conover had hooked up with his ex 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. Kroll was hurt by Conover’s choice to hide the Olindo 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 Olindo, who which she replied, “Twice. That’s it.” The North Carolina native then called Conover 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,” Kroll told his BFF, to which Conover replied, “Sometimes I feel like you’re trying to tear me down.” The pals continued to talk out their issues, with Conover calling Kroll out for making Olindo feel bad about what went down between the exes in Las Vegas.

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

“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,” Kroll claimed during the chat, to which Conover 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 Kroll 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’

Conover gave an update on Kroll during an August 2023 appearance on Bleav’s “It’s Complicated” podcast. “He really struggles with self-sabotage and self-destruction,” Conover said of his pal, noting viewers will see Kroll 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.”

Conover confessed that he and Kroll 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 Conover’s relationship with DeSorbo, he applauded Kroll 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,” Conover 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 Kroll for his rumored hookup with Shep Rose’s ex Taylor Ann Green.

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

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

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

Conover, meanwhile, exclusively told Us in fall 2023 that he called out Kroll both on and off camera for his shady hookup with Green. “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,” Conover 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.”

Credit: Gabe Ginsberg/Getty Images

Bar Buddies

Kroll and 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,” Conover 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 are hoping for a summer 2024 opening.

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