Austen Kroll Kissed Taylor Ann Green. Now Look Back His Other Romances.
The Bravoleb has had various flings and girlfriends across Southern Charm, Winter House, and Summer House.
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 both shows.
And, on occasion, his situationships have even overlapped a bit, causing drama amongst his friends.
In Southern Charm Season 9, things got even stickier as rumors flew that Austen may have crossed the line with his friend Shep Rose’s ex-girlfriend Taylor Ann Green (who is also besties with Austen’s most recent ex Olivia Flowers). In Episode 5, Austen finally admitted to Shep that he and Taylor had “kissed.”
And despite Austen sharing in Episode 12 that he’s “going to therapy, [he’s] trying to change, [he’s] trying to fix things,” he still found himself at odds with Olivia and various other cast members who took her side.
Below, we recap Austen’s extensive relationship history along with everything we know about his connection with Taylor.
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 up 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.’”
Austen Kroll says he “kissed” Taylor Ann Green in Season 9
During Season 8, Austen formed a friendship with Shep's then-girlfriend, 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 dropped in August 2023 along with a bombshell revelation: Austen admitted that “something happened” with Taylor at the beginning of the trailer, but didn’t provide any additional details.
Flash forward to Episode 5 (which first aired on October 12, 2023), and Austen confessed to Shep that he and Taylor had “kissed.”
“It was in a moment in a time of just, like, so much confusion for both of us,” Austen told his friend in the video above.
In an interview in the episode, Austen continued: “I have maintained with Taylor that, if something materialized between us, then, yes, of course we would tell our friends in the appropriate manner. But if nothing did materialize, then there was no reason to tell our friends and to hurt their feelings when their feelings don’t need to be hurt.”
Austen Kroll and Olivia Flowers' Relationship in Season 9
In Season 9, Olivia experienced an unimaginable tragedy with the loss of her brother, Connor. Since Austen had gone through something similar with the passing of his sister Kyle at a young age, he and Olivia reconnected a bit so he could be there for her during this difficult time.
However, lines were blurred again (at least ostensibly) in Season 9, Episode 8 when it was revealed that Olivia left her bra on an ottoman at Austen’s house. Austen later confirmed that Olivia had left her bra at his house, but said the two hadn't hooked up. Rather, he said, she had come over to his home to watch a movie, and she removed the undergarment to get more comfortable.
"We cuddled a little bit," he added. "She kissed me right on the chest and she f-cking left.”
During a panel at BravoCon 2023 in October, Olivia also denied that anything happened. "I just was getting comfortable!” she echoed, before adding, “Bonehead move.”
Still, in Season 9 during the cast trip to Jamaica, there was an “interesting” development, as Olivia put it: She found a Polaroid photo of herself kissing Austen on the cheek in his toiletry bag — which was never explained
Of course, the two found themselves on the rocks again in Episode 12 after Austen and Taylor’s kiss became the subject of media coverage. At a subsequent group dinner, Olivia called Austen a “a f-cking lying piece of sh-t” for the “sh-t storm” that he caused.
Austen Kroll and Olivia Flowers' Relationship Today
Back in Charleston in Season 9, Episode 15, Olivia and Austen again hashed out their feelings during a party to “christen” Whitney Sudler-Smith’s new “cottage/pub/office.” Olivia was shocked to learn that Austen was expecting an apology from her for her “inconsistent” feelings towards him.
“It’s not a good friendship,” Olivia told Austen. “It just seems like nothing is genuine... Look at the paper trail of pissed-off women you leave.”
When Austen accused Olivia of “flipping” the situation “on its head,” Olivia walked away from the conversation and seemingly any hope of reconciliation went out the door with her.
However, during Part 2 of the Season 9 reunion, Olivia revealed that she was in a new relationship with someone named Alex and that he is friends with Austen. Though Olivia and Austen still can’t quite see eye-to-eye on what went down between them, they’ve looked past it enough to peacefully vacation with mutual friends.
Austen Kroll and Taylor Ann Green rehashed their kiss at BravoCon 2023
Taylor revealed during a panel at BravoCon 2023 that she had been “blindsided” by Austen’s confession to her ex despite the fact that the pair agreed together to keep it a secret. She said she was especially concerned about him breaking their agreement since she is close with Olivia. “I try to laugh everything off at this point...” she said.
“I wanted to come out with the truth from the very get-go, and that wasn’t the case," she added. "And he’s sitting there going, ‘I’m feeling liberated’ and I was like, ‘Well I’m glad you feel liberated because I feel like a piece of poop.’”
Austen, however, defended his actions. “You had a decision earlier in the night,” he said. “I can’t tell you what to do... My friend came to me and asked me. What was I supposed to do? Just lie to Shep’s face? Was I supposed to lie to Shep? Was I supposed to lie to him again?”
That’s what Taylor had to do with Olivia, so she'd expected Austen to do the same with Shep. However, she concluded, “it would have eventually come out regardless.”
Originally published Sep 5, 2023.
