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Austen Kroll and Olivia Flowers' Relationship Timeline

Austen Kroll, Olivia Flowers
Austen Kroll, Olivia Flowers

Stephanie Diani/Bravo/NBCU Photo Bank

Southern Charm star Austen Kroll has introduced viewers to several new relationships over the years.

The reality TV vet is never afraid to share the details of his romances on-screen, whether it's a love triangle or an on-again-off-again fling, and his most recent relationship with Southern Charm newcomer Olivia Flowers is no exception.

Kroll and Flowers' close bond fueled rumors of a budding romance when season 8 first premiered — and the drama quickly started to heat up as Kroll's past girlfriends started making appearances. The Pillows and Beer podcast host first caught Flowers' attention when he slid into her DMs, though she was aware of Kroll's previous drama with Southern Charm's Madison Lecroy and Summer House's Lindsay Hubbard and Ciara Miller.

"I think he's very misrepresented," Flowers told Entertainment Tonight of Kroll's reputation with the audience. "He's very sensitive, and I think a lot of the times, he really does just speak his mind and say things how they are. And I think they can be misunderstood sometimes."

In the beginning of season 8, Kroll appeared to be hung up on his ex Lecroy, which Flowers admitted to ET was a red flag. And while Flowers said she had the intention of at "least being cordial" with Kroll's former girlfriend, the two ended up getting into a verbal altercation while filming, with Flowers storming off and flipping the bird at Lecroy.

Despite the situation with Lecroy, Kroll and Flowers appear to be going strong ahead of the season 8 finale, which premieres on Sept. 29, 2022.

From meeting as costars on Southern Charm to navigating the drama of past exes, here's everything to know about Austen Kroll and Olivia Flowers' relationship.

December 2021: Olivia Flowers supports Austen Kroll's beer release

Austen Kroll, Olivia Flowers, Shep Rose, Taylor Ann Green
Austen Kroll, Olivia Flowers, Shep Rose, Taylor Ann Green

Shep Rose Instagram

In December 2021, Kroll, the founder of Kings Calling Brewing Company, released two new flavors of Trop Hop, and Flowers attended the launch to support his new business endeavor.

Shep Rose posted a group photo of Kroll and Flowers arm-in-arm along with him and former girlfriend Taylor Ann Green from the event.

February 16, 2022: Austen Kroll and Olivia Flowers hang out with castmate Kathryn Dennis

Austen Kroll, Olivia Flowers, and Kathryn Dennis
Austen Kroll, Olivia Flowers, and Kathryn Dennis

Kathryn Dennis Instagram

On Feb. 16, 2022, Kathryn Dennis posted a selfie with Kroll and Flowers on Instagram with the caption, "Back in a charleston Hi."

In the comments, fans immediately began speculating about Kroll and Flowers' relationship.

May 2022: Austen Kroll and Olivia Flowers take a trip to California with Shep Rose and Taylor Ann Green

Austen Kroll, Olivia Flowers, Shep Rose, Taylor Ann Green
Austen Kroll, Olivia Flowers, Shep Rose, Taylor Ann Green

Taylor Ann Green Instagram

The couple joined Rose and Green on a trip to California in May 2022. Rose posted a few snaps from the vacation on Instagram, including several photos of Flowers and Kroll enjoying glasses of wine at a vineyard.

May 16, 2022: Olivia Flowers joins Austen Kroll on season 8 of Southern Charm 

Chleb Ravenell, Austen Kroll, Olivia Flowers, Leva Bonaparte, Craig Conover, Shep Rose, Kathryn Calhoun Dennis, Naomi Olindo, Venita Aspen, Taylor Ann Green
Chleb Ravenell, Austen Kroll, Olivia Flowers, Leva Bonaparte, Craig Conover, Shep Rose, Kathryn Calhoun Dennis, Naomi Olindo, Venita Aspen, Taylor Ann Green

Stephanie Diani/Bravo/NBCU Photo Bank

On May 16, 2022, Flowers announced she was an official new cast member of Southern Charm and shared the cast photo for season 8 on Instagram.

She captioned the photo, "Charmed I'm sure 💫."

June 23, 2022: Austen Kroll and Olivia Flowers go on a first date on Southern Charm

Dennis hosted a 1930's 'Great Katsby' themed party for her 30th birthday, which was attended by Kroll, Flowers, Rose, Green and their fellow Southern Charm castmates Leva Bonaparte, Craig Conover and Naomie Olindo.

Kroll introduced a new face to the group, Flowers, who had moved back to South Carolina during the pandemic. The two enjoyed a laid-back, stress-free night together until Kroll's ex Lecroy made an appearance. While Kroll claimed to not be bothered by her presence, Flowers was visibly peeved.

"We shouldn't be going on our first date and be talking about homegirl," she told the cameras.

June 25, 2022: Madison Lecroy throws a dig at Olivia Flowers on Instagram

On June 25, 2022, Lecroy posted on Instagram and seemingly shaded Flowers after she called Lecroy a "homegirl" during the first episode of season 8.

Lecroy captioned the solo shot, "I'd rather be a homegirl than a homely girl 😎."

In an interview with ET, Flowers revealed she did not respond to the dig, and that "[Lecroy] kept going with it too, I went from homely to homeless to trust fund trash, which I thought was impressive because who goes from homeless to trust fund trash in a day but no I didn't, I just let her have her time and relevance."

July 21, 2022: Austen Kroll and Olivia Flowers define their relationship on Southern Charm

After hanging out with each other at large gatherings and on double dates, Kroll and Flowers had a conversation about their relationship status during an episode of Southern Charm that aired on July 21. After the pair decided that they were not exclusive, Kroll told Flowers that she should continue to go on dates with other people.

August 4, 2022: Olivia Flowers talks about Austen Kroll on Watch What Happens Live

Andy Cohen, Kathryn Dennis, Olivia Flowers
Andy Cohen, Kathryn Dennis, Olivia Flowers

Charles Sykes/Bravo

On Aug. 4, 2022, Flowers appeared on a Watch What Happens Live episode alongside her castmate Dennis. During a round of "Can You Defend Him?" Cohen brought up the comparison of Kroll to a Honda Civic.

She snapped back, "Austen is the Range Rover. He's no Honda."

When Cohen asked if she thought Kroll had the right to be upset that Lecroy didn't tell him she was engaged, Flowers responded, "If she was completely out of his life and wasn't always trying to control him and come back in and sending him late night text messages, then of course I would think that is silly, but she is always trying to make her presence known in his life so I am sure that had something to do with it."

Cohen questioned, "She sends him late-night text messages?"

"Yeah, like the other night she sent him one and it was like 'I don't want to fight anymore' and … alright you're the only one on your shade tour. She had some lovely things to say about me on that tour," Flowers explained.

August 2022: Olivia Flowers says she and Austen Kroll share the "same sense of humor"

That same month, Flowers chatted with ET about her experience on the Bravo show and got candid about her romance with Kroll.

When asked if she could define their relationship, she said, "You will have to tune in and watch the rest of the season to find out, but we are in a very good place."

The next burning question asked was whether she saw a future with Kroll, to which Flowers responded, "I wouldn't … be involved with him how I have been if I couldn't."

She then shared that Kroll makes "her laugh constantly," and that they both have the "same sense of humor."

August 11, 2022: Olivia Flowers brings a date to the Southern Charm dog wedding

Patricia Altschul's dog Peaches and Rose's dog Little Craig tied the knot in November 2021 with a lavish pup wedding ceremony. In an episode of Southern Charm that aired on Aug. 11, viewers watched as several cast members attended the dog nuptials along with their significant others, including Conover and his girlfriend, Paige Desorbo. Flowers also came to the event with a plus one — her blind date Zach.

Kroll reacted with surprise, asking Green, "Who is that? Who is it?" After she replied, "It's Olivia's date," Kroll noted, "He's a handsome man."

Kroll then spent the afterparty hanging out with his former fling, Miller.

August 25, 2022: Austen Kroll and Olivia Flowers join the cast of Southern Charm on a trip to the Auldbrass Plantation

The cast of Southern Charm took a trip to the Auldbrass Plantation to film season 8, which later aired on Aug. 25, 2022.

In the episode, Flowers wrestled with her feelings toward Kroll after she heard from Olindo and Bonaparte that he was unhappy about the wedding date situation, and that he reacted by spending the evening with his ex, Miller. Shocked by the news, Flowers stayed clear of Kroll until he pulled her aside for a chat.

Kroll shared that he was really "bummed" since the wedding and that it is his fault for saying they should "take things slow" and "you did exactly what I told you to do."

He continued, saying he did not want to see her with anyone else, to which she responded, "Really?" and questioned him about what he did after the wedding.

Kroll told Flowers that he went off with other friends, specifically Miller, but Flowers quickly jumped in and said, "Did you think I didn't know about you and Ciara hanging out?"

Stammering, Kroll told her, "It was a great time to reconnect." In response, she called him out for being "full of s---."

Despite spending time with Miller, Kroll told Flowers that he had been thinking about her a lot, saying, "I do not want to date other people, I want to date you."

Flowers revealed the feelings were mutual and that going forward, they should just communicate with each other.

September 1, 2022: Olivia Flowers celebrates Friendsgiving at Austen Kroll's aunt's house on Southern Charm

Southern Charm cast at Friendsgiving
Southern Charm cast at Friendsgiving

Shep Rose Instagram

On Nov. 24, 2021, the Southern Charm cast gathered around the table to celebrate Thanksgiving. Viewers saw the event during an episode that aired on Sept. 1, 2022, when Kroll hosted a Friendsgiving with the castmates at his aunt's house.

Rose shared a photo of the group enjoying the holiday season with full bellies and sunset views. He wrote, "Embrace sunsets. Don't fight the feeling. Good friends, great casseroles. #friendsgiving."

September 22, 2022: Austen Kroll and Olivia Flowers pack on the PDA during a cast trip at the King and Prince Resort

Olivia Flowers, Austen Kroll, Craig Conover, Taylor Ann Green, Venita Aspen
Olivia Flowers, Austen Kroll, Craig Conover, Taylor Ann Green, Venita Aspen

Olivia Flowers Instagram

The Southern Charm cast escaped Charleston for a trip to the King and Prince Resort in St. Simons Island, Georgia, on Dec. 4, 2021, which later aired on Sept. 22, 2022.

During the episode, Flowers and Kroll were seen packing on the PDA and implied that they're more than friends. After they left the restaurant and returned to their vacation home, Flowers sat between Conover and Kroll, and cameras caught Flowers pulling Kroll in for a smooch on his cheek. Later on that evening, Kroll lifted Flowers into his arms and twirled her around the room as they both shared a kiss in front of the group. The next day, they spent the day with the crew shrimping, where they were seen cuddling and engaging in friendly beer competitions.

October 6, 2022: Austen Kroll and Olivia Flowers are "not" in a relationship

During part one of the season 8 reunion of Southern Charm, Kroll and Flowers clarified their relationship status after being questioned by Kroll's ex LeCroy.

Flowers confirmed that the pair are "not in a relationship," before Kroll added: "We both talked and were like, 'I don't want to ever lose you in the capacity that we've seen our friends…' or in the way that me and Madison, we don't speak."

However, the reality stars did confirm that their relationship turned romantic for a time after filming ended. But the timing was never right to make things official.

"When you came to me and you wanted to be 100 percent," Flowers directed at Kroll, "I was in the place where I was just mentally f----- because things with you were so complicated. I told you, 'I don't see it with us right now,' [but] I guess I imagined that we would get there. You were just like, 'OK, yeah, we'll be friends.'"