Southern Charm’s Austen and Olivia’s Relationship Timeline: The Way They Were

The look of love! Austen Kroll and Olivia Flowers’ courtship has had its ups and downs since they were first linked.

The Southern Charm stars sparked romance rumors in late 2021 when they were seen filming the Bravo series together and looking somewhat cozy. (Flowers, for her part, moved from Los Angeles back to South Carolina in August 2021.)

The speculation continued to grow as the Kings Calling Brewing founder was spotted on multiple group dates with Flowers, Taylor Ann Green and her then-boyfriend Shep Rose.

It wasn’t until May 2022 that Kroll confirmed he was off the market, exclusively telling Us Weekly how “excited” he was for fans to see Flowers on season 8 of Southern Charm — and to watch their relationship unfold.

“I’ve known her now for a year and a half,” he told Us at the time, noting that their early romance wasn’t always smooth sailing. “You will certainly see where it begins, then how it ends. And it certainly is some ebb and flows as I’m trying to figure it out.”

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The businessman gushed over his new flame, saying, “[She] comes from a good place. She’s extremely kind, you know, she has [a] backbone.”

One month later, viewers saw Kroll and Flowers’ first real date when they attended Kathryn Dennis’ Great Katsby bash during the season 8 premiere. “You remember Olivia? I like her,” Kroll told Rose during the episode. “She scared me when I met her. Now she lives here.”

The date, however, wasn’t without its drama as Kroll couldn’t help but freak out when his ex-girlfriend Madison LeCroy walked through the door. (Kroll and LeCroy split in December 2020 after more than two years together.)

“We shouldn’t be going on our first date and talking about homegirl,” Flowers said during the June 2022 confessional.

Despite their rocky moments on screen, the videographer told Us exclusively in August 2022 that she and Kroll were officially exclusive and in a good place.

“We’re just having fun. We traveled a bunch this summer. We went to really cool places, and you always get to know someone on another level when you travel with them,” Flowers said of her budding romance. “And we got to kind of relax once the cameras left and the shows stopped. We just kind of really got to know each other and figure out if this was something we wanted and we’re definitely in each other’s lives.”

Scroll down to see Kroll and Flowers’ romance from the beginning:

The “Pillows and Beer” podcast cohost and Flowers had their first date at Dennis’ Great Katsby party. The outing was later featured during the season 8 premiere in June 2022.

The duo were spotted filming Southern Charm with Dennis and Craig Conover.

The pair fueled dating speculation after Green shared a group snap of them all supporting Kroll’s Trop Hop launch in town. Flowers cozied up to her man in the photo while the clinical assistant stood beside her then-boyfriend Rose.

Dennis shared a sweet snap with the happy couple via Instagram, revealing she was back in Charleston with her costars.

Kroll was seen spending time with the photographer in Napa Valley, California, alongside friends Green and Rose.

Kroll exclusively confirmed to Us that he and Flowers were dating after months of speculation. “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,” the North Carolina native gushed, noting that their romance would be part of the Bravo series. “She truly, in my opinion, brings the charming back to our show.”

Flowers made her Southern Charm debut during the season 8 premiere as she attended Dennis’ 30th birthday bash as Kroll’s date. “Austen slid into my DMs, which is oh, so romantic,” she revealed during a confessional. “I would say it makes me a little giddy to see him.”

The Clemson University alum started feuding with Kroll’s ex-girlfriend LeCroy shortly after the season 8 premiere of the Bravo show. “I’d rather be a homegirl than a homely girl,” the hairstylist captioned an Instagram photo at the time, seemingly referring to Flowers calling her “homegirl” during the episode.

“Homely? More like homebody,” Flowers fired back via her Instagram Story while relaxing in a robe and eating chips. The following month, LeCroy exclusively told Us, “When I called her homely, [it] could have been worse. I was thinking, like, homeless because I don’t even think she lives with her mom and dad.”

Flowers, for her part, told Us in August 2022 that she is over the Greenville, South Carolina, native’s drama. “I went from homeless to full-on trash in less than a day. I thought that was impressive,” she joked, noting that LeCroy is “calculated.” Flowers concluded: “I don’t think much of her.”

Throughout the first few episodes of season 8, Kroll and Flowers experienced a few ups and downs. After a few group dates, the pair had some one-on-one time, which according to Flowers was consumed with talks about LeCroy following her engagement to Brett Randle. (LeCroy announced the happy news in October 2021, which is when much of Southern Charm was filmed.)

“I hate that our s–t has so much to do with Madison. I can’t even go on a normal date with you,” Flowers told Kroll during the July 21 episode. Kroll, for his part, got frustrated with his love after she invited LeCroy to her family’s oyster roast.

The beermaker confessed to Flowers during the July 28 episode, “What the hell? I felt slighted. It was like, ‘What the f—k is she doing here?’ … No one that I’m interested will be friends with her.” Flowers, however, insisted she wasn’t “friends” with his ex, but rather wanted to “coexist.”

The former Los Angeles resident sparked engagement speculation during an appearance on Watch What Happens Live With Andy Cohen when she wore a diamond ring on her left hand. “Are we going to talk about the ring on Olivia’s finger??” one fan wrote via TikTok alongside a clip from the talk show. A second user commented, “Is Olivia engaged?”

Flowers told Us later that month that the sparkler was simply a “gorgeous” ring from a stylist for the TV appearance. She also insisted that “despite how it looks” on Southern Charm, she is not in a rush to tie the knot.

“We are in a good place,” Flowers exclusively told Us, confirming that they aren’t seeing other people. “We had an incredible summer together and traveled and we’re still good.”

The one-time Laguna Beach resident also teased that the season 8 drama with Ciara Miller, whom Kroll briefly dated on Winter House and Summer House, didn’t affect their own bond.

“[Ciara] was in town and they did end up all going out that night. And of course, I was a little taken aback, but I was more so taken aback that he was upset about my date if he was gonna go and hang out with his ex,” Flowers told Us of the controversy that played out during the August 11 episode. “So that was more where I was coming from with my frustration, but we recovered from it and move[d] forward. And that’s what happens when you’re in that weird gray area with someone.”

During part 1 of the season 8’s reunion special, which was filmed in September 2022 and aired in October 2022, Flowers revealed that she and Kroll were “not in a relationship” at the moment.

“We both talked and we’re like, ‘I don’t want to ever lose you in the capacity that we’ve seen our friends,’” Kroll told host Andy Cohen during the October episode. “Or in the way like me and Madison don’t speak. She was like, ‘That would break my heart’ and it’s true.”

He continued: “You can call me a coward … for not taking that leap but, like, that s—t terrifies me.”

Flowers explained that the duo did date after filming for season 8 wrapped, claiming that ultimately Kroll pulled the plug on their romance. “I was ready to be in the relationship, but it was him that, like, couldn’t figure it out,” she said.

Kroll, meanwhile, revealed that he did want to be all-in on the relationship at one point but when that happened, Flowers wasn’t on board.

“When you came to me and wanted to be 100 percent I was at the place, mentally, [confused] because things with you are so complicated,” the California native said during the reunion. “I told you I don’t see it with us right now. I imagined that we would get there. And you were just like, ‘Then, yeah, we’ll be friends.’”

She added: “I was, like, really patient with him all these months while he was trying to figure out what he wanted and the one time I needed him to be patient with me, he wasn’t. He was like, ‘OK, well I tried and that’s that.’”

Kroll exclusively confirmed to Us that he and Flowers were not back together following the uncomfortable season 8 reunion, which filmed in September 2022 and aired in October 2022.

“I think that the reunion kind of took us, like, a little bit of shock,” the beermaker confessed to Us, referring to how caught of guard Flowers was during the taping when he got along so well with his ex LeCroy. “I didn’t really know how to handle it. I don’t know if I handled it in the best way.”

He continued: “I was so concerned going into reunion. The only thing that I wanted to come out on the other side with is, you know, [Olivia] and I being in a great place and I think that she was kind of taken aback at like how, you know, Madison and I were kind of bantering and she was like, ‘What is happening?’ You know?”

After the taping, Kroll revealed he and Flowers “took kind of, like, a little bit of time, but then we talked.” While the pair were keeping things platonic at the moment, the southern gentleman told Us, “I would never say never with her. She’s such an important person in my life and, like, she was huge for me, you know, this year to kind of get back to, you know, who I think that I am. So, I would never say never with that one.”

Leva Bonaparte exclusively told Us that the “ship has sailed” for Flowers and Kroll following their ups and downs earlier in the year.

“Austen was very into her the entire time filming. I mean he literally was just like, ‘This is gonna be my wife,’” Bonaparte recalled, referring to Kroll’s feelings toward Flowers while shooting both Southern Charm season 8 and Winter House season 2. “Olivia and I, before we started filming Southern Charm had a dual birthday — cuz our birthdays are a few days apart — at Bourbon N’ Bubbles. And he was just like, ‘Who’s that girl? I’m gonna marry her.’ He was very into her from the beginning.”

She added: “I just think that was what it was and it’s done.”