The Untold Story Behind Austen Kroll and Craig Conover's Unforgettable Friendship Journey

In the world of Southern Charm, friendships often come and go. However, when Austen Kroll joined the cast in season 4, his immediate connection with Craig Conover was undeniable.

Conover and Kroll formed a strong bond in 2016, when they began filming with the other residents of Charleston, South Carolina. Unlike the majority of the original cast, who hail from Southern aristocracy, both Conover and Kroll are hardworking individuals.

Their shared experiences of struggling to establish their careers and navigating the highs and lows of their relationship created a strong bond between them. However, complications arose when Kroll and Conover became romantically involved with Kristin Cavallari in 2020 and 2021 respectively, leading to dramatic situations.

Despite Cavallari's denial of being involved in a love triangle in July 2021, Conover revealed on a Summer House episode in January 2022 that he had previously been intimate with her. He further claimed that Kroll had become jealous of their encounter, expressing his disapproval to Paige DeSorbo on the show and stating that Kroll "disliked the fact that I kissed [Kristin]."

Nevertheless, Conover and Kroll appear to have moved past the conflicts, as they have been co-hosting their podcast "Pillows and Beer" since 2020.

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

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

When Austen Kroll joined the Southern Charm cast in season 4, viewers couldn't help but notice the instant connection he formed with Craig Conover. While most of the original cast comes from Southern aristocracy, Conover and Kroll are both hardworking individuals based in Charleston, South Carolina.

Their shared experiences of struggling to establish their careers and navigating the ups and downs of their relationship created a strong bond between them. However, complications arose when Kroll and Conover became involved with Kristin Cavallari in 2020 and 2021 respectively, leading to drama.

In July 2021, Cavallari denied being part of a love triangle, while Conover claimed during a January 2022 episode of the reality show Summer House that he had previously been intimate with her. He further alleged that Kroll became jealous of their involvement, expressing his displeasure to Paige DeSorbo by saying that Kroll "hates that I was making out [with Kristin]." Despite the turbulence, Conover and Kroll appear to have moved past it 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 initially featured on the Bravo series in season 4, which was shot in the summer and fall of 2016. He officially entered the scene in April 2017 and swiftly developed a close friendship with Conover.

Credit: Courtesy Craig Conover/Instagram

Trolling Craig

In August 2017, while traveling, Kroll playfully teased his friend. He shared a photo of the two of them watching Southern Charm on the plane, captioning it, "F—king Craig on TV on the plane ... ugh."

Conover then reposted the picture, jokingly wondering if any best friends ever say anything nice to each other. He added hashtags like #thanksgaber, #southerncharm, #charmedairways, and #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.

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Leaving Him Hanging

Conover angrily confronts Kroll in an episode of season 6 of Southern Charm after finding himself abandoned with a group of unfamiliar people at a bar. The owner of Sewing Down South reprimands his friend for leaving prematurely, a decision that Kroll attributes to the advice of their mutual friend Chelsea Meissner.

"I harbored a lot of anger towards him for abandoning me, primarily for my own self-centered reasons," Conover admitted to Decider in July 2019. "I was furious because I relied on you at the end of the night and I didn't have anyone else."

During their joint interview, Kroll playfully teased that his best friend suffered from "separation anxiety," which explained his freak-out when left alone at the bar. "I have to reassure him, Craig, you'll be okay. Just look around and you'll find a girl who's interested in you, and everything will be alright," Kroll added, prompting Conover to jest, "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

The duo collaborated in May 2020 to create special videos for Mother's Day on the platform Cameo. "Whenever we appear in the media together, our signature introduction is, 'Hey guys, I'm Austen, and I'm Craig. And together we're the Hardy Boys!'" Kroll humorously remarked in the caption of his Instagram post.

Credit: Courtesy Austen Kroll/Instagram

Kristin Cavallari Friendship

"She arrived in town accompanied by her friend Justin, and the four of us, including Craig, enjoyed a delightful dinner," Kroll exclusively revealed to Us about their friendship in October 2020. "We have remained in contact ever since and formed a close-knit group chat. This group chat is always active and it brings us so much joy. We had an incredible time with them, and I am planning to visit them in Nashville in the near future."

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

During the season 7 reunion in February 2021, Conover accused Kroll's ex-girlfriend, LeCroy, of being involved with a married former MLB player. LeCroy later confirmed that the person in question was Alex Rodriguez, who was engaged to Jennifer Lopez at the time. However, the hairstylist denied any physical relationship with Rodriguez. A source close to Rodriguez clarified that he had never even met LeCroy. After Kroll shared details about his troubled relationship with LeCroy, Conover supported him by expressing his frustration and calling her a terrible person.

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.

Conover described the series in October 2021 as "a little more raw." He explained that viewers are accustomed to seeing them in formal attire and social settings, but this time they will be depicted in their everyday lives. Kroll agreed, emphasizing that this new side of their personality will also reveal their flaws, but he believes it will be a well-rounded portrayal.

Credit: Courtesy Craig Conover/Instagram

Minnesota Summer

In July 2021, Conover shared a collection of social media pictures, capturing the essence of Minnesota, peanuts, the 4th of July, America, and the unforgettable Summer of 69. The attorney commemorated the holiday weekend alongside his closest companion and Winter House co-star, Luke Gulbranson.

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

Austen Approves of Paige

In the summer of 2021, Conover and his Winter House colleague, DeSorbo, embarked on a romantic relationship. Their love story was publicly acknowledged in September of that same year, when they made an appearance at Amanda Batula and Kyle Cooke’s wedding.

One month later, Kroll expressed his thoughts on his friend's relationship. Speaking to E! News in October 2021, he confidently stated, "I completely understand why they get along a thousand percent. I actually predicted this would happen while we were in the house, but Craig was in a relationship at the time. You'll witness some interesting developments there. I definitely saw this coming."

Furthermore, Kroll observed, "They connect with each other so effortlessly. Craig seems to align more with her personality compared to others in the house. Their laughter, banter, and overall compatibility are what I believe contribute to their successful dynamic."

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 revealed on a recent episode of Summer House in January 2022 that he and Cavallari were involved in a romantic relationship. Their connection had initially sparked love triangle speculations which also included the Hills alum and Kroll back in July 2021.

Conover admitted to DeSorbo that he had been involved with Cavallari in the past, stating that Kroll disapproved of their physical intimacy. This statement seemingly confirmed that Conover and Cavallari had a romantic history. However, a source close to Cavallari denied any such involvement and accused Conover of using her name for personal gain.

In a later episode of Summer House, DeSorbo disclosed further details about text messages exchanged between Conover and Cavallari regarding their hookup. According to DeSorbo, Cavallari expressed her concern about being portrayed negatively and gave Conover permission to pursue her if he wished, as long as it didn't reflect poorly on her. Conover responded by accusing Cavallari of lying on Instagram and emphasizing that they had indeed engaged in a sexual relationship.

Credit: Stewart Cook/Shutterstock

‘Summer House’ Misstep

Conover disclosed to Us in March 2022 that he ceased communication with Kroll for approximately two months upon discovering his actions on Summer House season 6. The attorney expressed his dissatisfaction with the way Kroll treated their mutual friend Ciara Miller, whom Kroll previously dated on Winter House. "I felt extremely let down," stated the author of Pillow Talk: What's Wrong with My Sewing? "I don't watch the shows, for the sake of my own well-being, but when I found out that he kissed Lindsay [Hubbard] right after kissing Ciara, I was like, 'Dude, that's exactly what Lindsay wanted to happen.' He really hurt Ciara... I was just really disappointed in him." Conover mentioned that they have since reconciled. "Austen is currently in a much better place. Since last fall, [Austen], Paige, and Ciara have been working on self-improvement. So I feel a bit bad that he has to relive all of this now, eight months later," he shared with Us. "At present, we're on good terms. Him and I are about to go on tour and we have resolved all of our issues. But it wasn't the best display."

Credit: Bravo

Battle Royal

The tension between Conover and Kroll reaches a peak in season 8 of Southern Charm, with a noticeable escalation. In the trailer for the May 2022 season, Kroll directs his words to his friend, urging him to calm down with a strong expletive. The intense struggle between the two friends unfolds as they grapple near a car and eventually end up on 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 in June 2022, Conover and Kroll's relationship took a hit when the attorney accused Kroll of sharing sensitive details about his life with others. Feeling betrayed, Conover confided in his friend John Pringle that he no longer trusted Kroll and had stopped confiding in him.

At Kathryn Dennis' Great Katsby party, Kroll discovered that Conover had slept with his ex Olindo in Las Vegas, despite previously claiming that nothing had happened. Feeling deeply hurt, Kroll expressed his disappointment, stating, "Craig is supposed to be my best friend, but this incident reveals the true state of our relationship."

The friends' unresolved issues from the premiere carried over into season 8, episode 2, which aired later that month. Kroll, feeling hurt by Conover hiding the Olindo hookup, sought answers from the France native to uncover the truth about what happened in Vegas. "Did you and Conover only sleep together once, true or false?" Kroll asked Olindo, to which she replied, "Twice. That's it." He then labeled Conover as a "good liar," insisting that Conover had only admitted to sleeping with her once.

Credit: Courtesy Austen Kroll/Instagram

Talking It Out

The long-time friends reconciled during the airing of season 8, episode 3 in July 2022. Kroll expressed confusion as to why Conover was distancing himself, to which Conover responded with feelings of being torn down by Kroll. The friends continued their conversation, with Conover addressing Kroll's behavior towards Olindo regarding their past in Las Vegas.

Kroll, who considered himself a strong supporter of Conover, admitted to feeling like an outsider when he learned about the hookup from someone other than Conover. He also acknowledged that it was not his place to know whether Conover's current girlfriend, DeSorbo, was aware of their past involvement. (Conover previously disclosed that DeSorbo was aware of everything regarding Olindo.)

"When you were single and didn't want to be alone, we used to spend a lot of time together. But then you got a girlfriend and seemed to abandon our friendship," Kroll stated during their conversation. Conover immediately responded, questioning why he should make an effort to hang out with someone who constantly tries to undermine him. Despite this, the author of Pillow Talk began to retract their statement, expressing a desire to put the toxicity behind them and rekindle their friendship.

Credit: Todd Williamson/Bravo

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

During an August 2023 appearance on Bleav's "It's Complicated" podcast, Conover provided an update on Kroll. Describing his friend, he acknowledged Kroll's struggle with self-sabotage and self-destruction. Conover mentioned that viewers can expect to witness Kroll's recurring battle with his love life in the upcoming ninth season of Southern Charm. Reflecting on their dynamics, Conover compared their relationship to trying to convince someone to do something against their will, stating, "You can lead a horse to water but you can't make them drink." He admitted to feeling frustrated at times, likening his efforts to holding Kroll's head underwater with no avail. However, Conover admitted that Kroll feels the same way about him.

Conover also disclosed that their friendship had experienced significant relationship issues in the past. However, they have become better at communicating and have developed a relationship dynamic akin to an old married couple. Conover jokingly attributed their problems to their contrasting personalities, remarking that understanding each other can be a challenge.

When it comes to Conover’s relationship with DeSorbo, he praised Kroll for his unwavering support. "He acknowledges and appreciates my happiness and the life I am leading, but it's also crucial for me to invest effort," Conover expressed. "Both parties must contribute effort to sustain the relationship. Thankfully, he truly respects the bond that [Paige and I] share."

Credit: Bravo

Craig Has Thoughts About Austen’s Season 9 Drama

In September 2023, when season 9 of Southern Charm debuted, the attention was focused on Kroll due to rumors about his involvement with Taylor Ann Green, the ex-girlfriend of Shep Rose. Kroll acknowledged in a September 2023 episode that Green, who is close friends with Kroll's former girlfriend Olivia Flowers, stayed over at his place, but assured Rose that she slept in a separate room. Nevertheless, Conover remained skeptical and expressed his concerns to Rose in the following episode.

During a conversation with Rose, Conover made allegations about Kroll, stating that he had slept with multiple girls that Conover had previously dated. Conover discovered this information years later. Rose also claimed that Kroll had engaged in similar behavior with him, referring to their former castmate Meissner. Kroll had pursued Meissner while Rose was away on a trip during season 4. Conover emphasized that Kroll's credibility regarding his interactions with girls is questionable.

Eventually, Kroll admitted to Rose in an October 2023 episode that he had lied. He confessed to kissing Green after both of their breakups. Despite this discovery, Rose chose to forgive Kroll. However, Flowers, visibly upset, was disappointed that Green had not been completely honest about her relationship with Kroll.

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Conover revealed to Us in fall 2023 that he confronted Kroll both on and off camera regarding his questionable fling with Green. "I make it a point to communicate with Austen openly and transparently, sharing everything I say to his face when we are being filmed," Conover revealed to Us. "Every person is unique, and I wouldn't necessarily label Austen as a poor friend to Shep. However, I personally choose to distance myself from someone once my friend ends their relationship with them," he disclosed. "Of course, not everyone follows the same approach as me. If someone were to do that to me, I would no longer consider them to be a friend. But that is solely my perspective."

Austen Kroll

Craig Conover

Southern Charm

Winter House