Southern Charm’s Austen Kroll’s Dating History: Chelsea Meissner, Madison LeCroy, Ciara Miller and More

Credit: Bravo (3)

Southern Charm’s Austen Kroll’s Dating History: Chelsea Meissner, Madison LeCroy, Ciara Miller and More

A tangled web. Austen Kroll has bared it all during his time on Southern Charm — including taking fans inside his relationship highs and lows. The Kings Calling Brewing founder joined the cast of the Charleston-based series during season 4 in 2017. He has since given OG stars Shep Rose and Craig Conover a run for their money in the romance department. “Austen has some pull on women. I don’t know,” Southern Charm alum Cameran Eubanks exclusively told Us Weekly in April 2022. “I mean, I’ll give it to the guy, he’s tall. He smells good. I don’t know what it is, but yeah, women love Austen.” The One Day You’ll Thank Me author added: “He’s never had a problem [getting a girl].” Kroll first turned heads in 2017 when he and Rose got into it over their feelings for costar Chelsea Meissner. Ultimately, she chose to pursue a relationship with Kroll, but it didn’t last long, and the “Pillows and Beer” podcast cohost rebounded with Meissner’s friend Victoria Bolyard. It wasn’t long before some eagle-eyed fans noticed that Kroll appeared to be going for the same women that Rose had either dated or hooked up with. [jwplayer 98miUBty-zhNYySv2] “Victoria never dated Shep and neither did Chelsea to be totally honest. He doesn’t [date anyone],” Kroll said during a July 2018 appearance on Watch What Happens Live With Andy Cohen. “It always sat heavy in my stomach that Shep had some tomfoolery with one or two of the girls that I have dated.” Despite a few messy on-camera romances, Kroll tried his hand at love again with Madison LeCroy, who joined the Southern Charm cast during season 6. Their tumultuous relationship ended in December 2020. “The past two weeks is the longest I’ve ever gone without talking to her,” Kroll exclusively told Us after the split, noting that he was “heartbroken” over the breakup. “So, it’s like I cut off my addiction cold turkey. … It just hasn’t been easy.” The University of Alabama alum hasn’t let his rocky relationship with LeCroy plague his dating life as of late — having sparked hookup speculation with Kristin Cavallari in late 2020. Kroll has also romanced several more Bravo personalities in the years that have followed. Scroll down to relive all of Kroll’s high-profile relationships: [podcast_block]

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Chelsea Meissner

The hairstylist briefly romanced Kroll during season 4 of Southern Charm in 2017. Kroll raised eyebrows in June 2018 when he seemingly hinted there was no spark between him and Meissner ahead of their split. “I need a woman with sex drive,” he wrote via Instagram after a fan claimed he didn’t try hard enough with his former castmate.

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Victoria Bolyard

Kroll moved on with Meissner’s friend during season 5 of the Bravo series, which aired in 2018, but the relationship didn’t last. In June of that year, the TV personality claimed that Bolyard was aggressive with him off camera after viewers witnessed her tossing her beverage at him.

“After she threw the drink on me, she followed me home and threw a rock through my window and I had to call the cops,” Kroll alleged via Instagram in June 2018. “That was the third time she’s had similar freak outs. I’m in a tell [all] mood tonight.”

One month later, Bolyard accused the beermaker of “gaslighting and bullying” her during their relationship after a video surfaced of Kroll allegedly cheating on his then-girlfriend LeCroy.

“I was the one girl who didn’t cheat on him or blow up his character flaws on national TV, but he still chooses animosity toward me,” Bolyard wrote via Instagram at the time, seemingly referring to Kroll’s claims that she was crazy for allegedly throwing a rock at his window following an argument.

Credit: Courtesy of Madison LeCroy/Instagram

Madison LeCroy

The hairstylist dated Kroll on and off for two years before LeCroy exclusively told Us in December 2020 that they called it quits for good. “We are not together right now. I am 1,000 percent single, and so is he,” she said at the time. “So, ladies, if you want him, you can have him.”

The Greenville, South Carolina, native moved on with Brett Randle, whom she got engaged to in October 2021.

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Kristin Cavallari

The Laguna Beach alum was rumored to be hooking up with Kroll and his BFF Craig Conover in late 2020 after the trio were seen hanging out in Nashville. Cavallari denied the romance in July 2021, saying, “I haven’t been involved in a love triangle since I was in high school. … I haven’t dated anybody in a few months. These two guys who I have been linked to for the past year are my friends. That’s it.”

The alleged encounter made headlines again in January 2022 after Conover claimed during an episode of Summer House that he was the one who was intimate with Cavallari not Kroll. “I’ve hooked up with her before,” the Sewing Down South founder told Paige DeSorbo on the show, which was filmed in summer 2021. He added that Kroll “hates that I was making out [with Kristin].”

One month later, a source exclusively told Us that Conover was “making it up” and that Cavallari “never hooked up” with the Delaware native.

Credit: Stephanie Diani/Bravo

Ciara Miller

While filming season 1 of Winter House in February 2021, Kroll struck up a vacation romance with Miller. The twosome’s fling ended later that year due to the pair’s distance. Miller, however, wasn’t over Kroll when he came to visit the Hamptons on season 6 of Summer House, which filmed in summer 2021.

Despite being flirty during his stay in New York, Kroll made out with Lindsay Hubbard, which ultimately led to the women being pitted against each other. Miller revealed during the season 6 reunion special, which aired in May 2022, that she and Kroll hooked up again following their fight over the love triangle, but vowed it was the last time.

Credit: Sean Zanni/Bravo

Lindsay Hubbard

The Summer House star had a fling in 2018 with Kroll, which he confirmed four years later. The duo have since maintained that they are platonic, but their flirty dynamic has rubbed many Bravo stars the wrong way over the years.

Kroll made waves during summer 2021 when he went to the Hamptons for Hubbard’s 35th birthday, which played out on season 6 of the series. After making out with the publicist, he told his former flame Miller about the incident, which led to their love triangle imploding.

Hubbard and Kroll’s relationship hit another road bump in October 2021 when the southern gentleman picked Miller as the better cuddler and kisser during an appearance on Watch What Happens Live With Andy Cohen. Hubbard, who moved on with Carl Radke in fall 2021, exclusively told Us in April 2022 that she and Kroll had “recently” talked about their fallout.

Credit: Stephanie Diani/Bravo

Olivia Flowers

Kroll was first linked to Flowers in December 2021 while filming season 8 of Southern Charm. The duo’s budding romance was teased in the official trailer for the show, which dropped in May 2022. The Bravo personality confirmed his relationship with the photographer to Us that same month.

“Olivia is this lovely, lovely woman who is now a cast member, which we can say. I’m just so excited for people to meet her,” Kroll exclusively told Us at the NBCUniversal upfront presentation. “She truly, in my opinion, brings the charming back to our show.”

He added: “You will certainly see where [our romance] begins, then how it ends. And it certainly is some ebb and flows as I’m trying to figure it out.”