Austen Kroll's Dating History: Chelsea, Victoria, Madison, Ciara, Olivia, & More

Austen Kroll has certainly put himself out there when it comes to dating and relationships. Between four seasons on Southern Charm and two seasons on Winter House, the Trop Hop beer founder has found himself in a number of relationships and situationships with other cast members on either show.

And, on occasion, his situationships have even overlapped a bit, causing drama amongst his friends.

Now, as Southern Charm is headed into Season 9 (it premieres Thursday, September 14, at 9/8c), Bravo fans are anxiously awaiting to discover what exactly Austen meant when he said “something happened” between him and Shep Rose’s ex-girlfriend Taylor Ann Green in the trailer (available above).

Before we unpack his latest potential fling, let’s relive Austen’s extensive relationship history.

Austen Kroll dated Chelsea Meissner on and off in Southern Charm Seasons 4 and 5

In his freshman and sophomore seasons on Southern Charm, Austen was captivated by fellow cast member Chelsea Meissner. (So was Shep, but ultimately Austen was the one to win Chelsea’s affection.) By July 2017, Austen confirmed he and Chelsea were no longer together, but they remained on good terms as friends.

"I talk to her all the time, great friends and the one thing that she said was, 'You know, we're at different aspects of our life,'" he said. "I like to go get a beer at 3:00 in the afternoon if I can. It's a part of my job. It's not really her M.O."

Austen Kroll dated Chelsea Meissner’s friend Victoria

Before he dated Chelsea, Austen was torn between her and her friend Victoria. But after it didn’t work out with Chelsea, he gave it another shot with Victoria.

"Victoria and I, we kind of just mesh together," he shared with Craig Conover in Season 5.

In a 2018 interview with The Daily Dish, Austen compared his relationship with Victoria to the one he had with Chelsea. "Trying to get Chelsea out and about is like pulling teeth,” he spilled. “Victoria, she gets off work and she's like, 'Let's go to happy hour.' I'm like, 'Yes! What a breath of fresh air. Let's go do that. Let's go have fun together. Let's do all of the things.'"

Austen Kroll and Madison LeCroy dated on and off starting in Southern Charm Season 6

Madison LeCroy made her Southern Charm debut as Austen’s new girlfriend in Season 6. "She's kind of like the hot topic. She seems to have made quite the impression," Austen told The Daily Dish Podcast about Madison in May 2019. "I know that she's nervous.”

However, Southern Charm fans know quite well that Austen and Madison had their fair share of drama throughout their relationship, including multiple breakups and make-ups. Madison described Austen as her "twin flame" and "the antichrist of your love" in an August 2019 interview with The Daily Dish Podcast. "Like you're not supposed to be with this person, but you can't help [being] with him," she said.

In Season 7, they broke up on camera, although they continued to talk after breaking up. By December 2020, Madison confirmed that they had called it quits for good. Although the two had a tumultuous relationship following their breakup, as of May 2023, they’re in a good place.

Austen Kroll and Ciara Miller shared a connection on three Bravo shows

In Season 1 of Winter House, romance sparked between Austen and his house mate Ciara Miller. In one episode, Austen took Ciara on a date, and the two shared a sweet kiss.

During Summer House Season 6, Ciara had hopes that she and Austen might rekindle their fling when he paid a visit to the Hamptons, but at that time, Austen had other interests (more on that below).

In Southern Charm Season 8, it was revealed that Austen and Ciara had hooked up after the dog wedding.

The two hoped to be on the same page when they returned to Vermont for Winter House Season 2, but it didn’t take long for the two to disagree again.

While appearing Watch What Happens Live with Andy Cohen in December 2022, Ciara shut down any possibility that they would get back together. “I’ve never been more finished, more done in my life,” Ciara told Andy Cohen. “Wrap it up with a bow.”

Austen Kroll and Lindsay Hubbard hooked up but never officially dated

Though they were never officially a couple, Austen and Summer House’s Lindsay Hubbard had a close friendship — with benefits. They had a fling while Madison and Austen were in a “gray area” in their relationship.

On Winter House Season 1, Lindsay even told Austen that she was in love with him, but Austen told Lindsay he didn’t want to “f-ck things up” with their friendship... and he decided to pursue Ciara instead).

The tables turned in Summer House Season 6, however, when Austen visited the Hamptons and shared a kiss with Lindsay, despite Ciara’s hopes that she might rekindle things with him.

But in October 2021, Austen appeared on WWHL to dish on the drama with Ciara and Lindsay, and he said Ciara was the better kisser.

During her WWHL appearance a month later, Lindsay called Austen’s comments “very humiliating” and the situation caused a rift in their friendship.

Austen Kroll and Olivia Flowers’ relationship played out on Southern Charm Season 8

Austen and Olivia Flowers were first linked in 2021, and fans saw their romance play out in Season 8 of Southern Charm. In one episode, Austen told Craig of Olivia, "She's very cool. And she's chill. And she's level-headed.”

During Part 1 of the Season 8 reunion, Austen explained that he and Olivia ultimately called off their romance out of fear of jeopardizing their friendship. “Look at all this turmoil up here,” he said, turning to his fellow Southern Charm cast members. “We both talked and were like, ‘I don’t want to ever lose you in the capacity that we’ve seen our friends.’”

The Season 9 trailer addressed rumors about Austen Kroll and Taylor Ann Green

During Southern Charm Season 8, Austen formed a friendship with Shep’s girlfriend at the time, Taylor. Following Shep and Taylor’s split — which Taylor confirmed in August 2022 — there were rumors that Austen and Taylor had become more than friends.

At BravoCon in October 2022, Austen and Taylor shut down those rumors with Taylor noting they are “totally not together."

The Southern Charm Season 9 trailer (which you can watch by scrolling to the top of this page) dropped in August 2023, along with a bombshell revelation: Austen said that “something happened” with Taylor at the beginning of the trailer, but he didn’t provide any additional details. The alleged hookup is at the center of several additional conversations in the trailer, many of which end in tears.