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

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.

Meissner announced in October 2023 that she gave birth to her first baby one month prior.

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.

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.”

LeCroy moved on with Brett Randle, whom she married in November 2022. 

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.

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.

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. Hubbard and Radke, meanwhile, called off their engagement in August 2023. Hubbard announced in July 2024 that she is pregnant with her and boyfriend Turner Kufe’s first baby.

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.”

Flowers confirmed during the season 8 reunion, which was filmed in September 2022, that she and Kroll had called it quits. Flowers moved on in May 2023 with Alex Williams, whom she met at a wedding in Texas. The couple got engaged in September 2024.

Kroll and Green made headlines in March 2023 when rumors surfaced that they had secretly hooked up after their respective splits from Flowers and Rose. Kroll and Green denied the fling on several occasions, but Kroll confessed during a season 9 episode of Southern Charm, which filmed in early 2023, that he did “kiss” Green.

During a November 2023 episode of the Bravo series, Kroll claimed that he and Green “didn’t sleep together.” He alleged to pal Conover that Green “kinda made a move on me, if I’m being honest,” explaining that the kiss took place in Charleston shortly after they returned home from filming the season 8 reunion in NYC.

Even though their kiss — and choice to hide it — hurt both Flowers and Rose, Kroll admitted he had no regrets. “I don’t necessarily mean that the kiss didn’t mean anything, but Taylor and I did not end up dating,” he asserted on the show. “We talked and decided we were better off as friends. I thought that we could just bury it and keep a secret from everyone. That’s what I regret doing.”

Green exclusively told Us in October 2023 that she was dating a man named Gaston, who was Southern Hospitality star TJ Dinch’s roommate.

Flowers confirmed in November 2023 that Kroll was dating someone new. Kroll, however, didn’t go public with the romance until February 2024, sharing photos with Pratt on a trip to Mexico. Kroll and Pratt returned to Mexico City in June 2024 alongside his Southern Charm costar Rodrigo Reyes and his now-fiancé, Tyler Dugas.