Kristin Cavallari and Craig Conover’s Relationship Timeline: From DMs to Austen Kroll Love Triangle Rumors

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Kristin Cavallari and Craig Conover’s Relationship Timeline: From DMs to Austen Kroll Love Triangle Rumors

Things are getting messy! Kristin Cavallari’s friendship with Craig Conover and Southern Charm pal Austen Kroll has been the cause of controversy on more than one occasion — and the drama doesn’t appear to be stopping anytime soon. The Uncommon James founder first made headlines with her newfound friends in the fall of 2020 after splitting from husband Jay Cutler in April of that year. “She came to town with her friend Justin and the four of us [with Craig] had dinner,” Kroll exclusively told Us Weekly about their friendship in October 2020. “We’ve all been in contact ever since. We’re in this, like, big old group chat, and the group chat is active. We had a blast with them and I’m gonna take a trip to see them in Nashville sometime soon.” However, as the year came to an end, Cavallari’s relationship with Kroll, specifically, appeared to rub his ex-girlfriend Madison LeCroy the wrong way. The fellow Southern Charm star, who dated Kroll on and off until December 2020, caused a stir when she claimed that the beer maker was still into her amid speculation that he was getting flirty with Cavallari. “Trust me if he was with her, he wouldn’t be sending me songs at midnight. bless,” LeCroy wrote via Instagram in December 2020, referencing her ex and his alleged new flame. (The hairdresser has since moved on with Brett Randle, whom she got engaged to in October 2021.) The same month, Conover gave Us insight into his and Kroll’s dynamic with the cookbook author and her best friend Justin Anderson — both of whom they saw while visiting Nashville in December 2020. “We’ve been having a lot of fun. It was a new friendship. Kristin had reached out to me a couple months ago and she came with Justin,” the Charleston School of Law alum exclusively said in December 2020. “He hit it off with them. We were down in Nashville filming the first episode of our podcast ‘Pillows and Beer,’ and she’s our first guest. It’s just one of those things — we just all hit it off and were great.” [jwplayer H33yUVlN-zhNYySv2] Four months later, Conover again sang Cavallari’s praises while promoting the opening of his flagship Sewing Down South store. “She is great. Her and Justin are awesome,” he gushed to Us in April 2021. “She just opened her new store. … I actually used that as an example, and I was like, ‘Can we do this?' [And she's] like, 'Yes, Craig, maybe in five years, if you’re here every day and you really work.’” Cavallari’s friendship with Conover and Kroll, however, turned heads again in July 2021 when she was accused of being in a love triangle with the men. “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 former MTV personality said via her Instagram Story at the time, denying that she had a sexual relationship with either guy. “I’ve never dated either one of them. I can guarantee that I’m not going to date either one of them. It’s possible for a grown woman to be friends with a grown man.” Conover, for his part, claimed during a January 2022 episode of Summer House — which taped in early July 2021 — that he had in fact hooked up with Cavallari. A source close to Cavallari denied the romantic relationship to Us in February 2022. Scroll down to relive Cavallari’s friendship with Conover and Kroll through the years — and see a full breakdown of her alleged hookup with the attorney: [podcast_block]

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October 2020

The Bravo star’s friendship began in the fall of 2020 over social media, before Cavallari came to Charleston in October of that year.

“She slid into Craig’s DMs and was like, ‘I’m coming into town,’ so we all went to dinner,” Kroll said during a December 2020 episode of Watch What Happens Live With Andy Cohen. “We all kinda hit it off. We wanted to go and visit them, and we did. We all get along so well.”

Credit: Courtesy of Justin Anderson/Instagram

December 2020

The two reality stars were spotted spending time with Cavallari and her BFF Anderson in Nashville a few months after they initially met. During the hang out, the Balancing in Heels author sparked romance speculation with Kroll, not Conover, but she quickly squashed those rumors via social media.

“I didn’t realize I wasn’t allowed to have FRIENDS that are guys,” she captioned a boomerang of herself at the time. Kroll, for his part, exclusively told Us in December that he was not “trying to cause problems,” noting that the duo “just had fun with our friends” during his visit.

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December 2020

Amid rumors that Kroll and Cavallari were becoming more than just friends, Conover exclusively told Us that he’d support them if they ever got together — noting the friend group were already pretty close.

“I think you saw our chemistry the other night and when Taylor Swift comes on, all of the walls come down and apparently we go Live,” the College of Charleston alum said. “We’ll have to see what happens. I don’t know. I can’t speak for them, but I think you’ll see a lot of the four of us in the future.”

Conover explained that Kroll needed to “heal from his trauma [with ex Madison],” but he would “be fine with it” if his pal started seeing Cavallari. “I think it would be great. Two of my great friends dating is fun!” he added.

Credit: Courtesy of Madison LeCroy/Instagram; Mark Humphrey/AP/Shutterstock

January 2021

While Conover claimed he was OK with Kroll possibly hooking up with Cavallari, the Kings Calling Brewing founder’s ex-girlfriend LeCroy wasn’t as happy with the idea. After sparking her own romance with Cavallari’s estranged-husband Cutler in January 2021, things turned sour fast when the southern belle seemingly shaded the Hills alum on social media.

LeCroy then shared her alleged text messages with Cutler in order to prove that he pursued her, affectively ending their brief fling. The former spouses, however, showed a united front amid the drama, with Cutler and Cavallari posing together on Instagram later that month. “The world is full of users. 10 years. Can’t break that,” the caption read.

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April 2021

Conover exclusively told Us that there was a chance that Cavallari could appear on Southern Charm, revealing that he expected to her to attend the opening of his Sewing Down South flagship store in Charleston later that year.

“I hope so. It’s not ruled out at all,” he teased. “If they’re at the party, then yeah. I think some of our friends from the past six months, you’ll get to see a decent amount of them, which will be really fun.”

Later that month, the mother of three exclusively told Us that she had no plans of starring on the Bravo series anytime soon.

“They say, ‘Never say never,’ but I can confidently say I’m never going to do Southern Charm,” the Very Cavallari alum said. “I love Craig. I don’t know! I don’t know why he was saying that stuff.”

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May 2021

Things started to heat up between Conover and his Winter House castmate Paige DeSorbo, but the pair kept their romance on the down-low for months. When DeSorbo left for the Hamptons to film season 6 of Summer House two months later, she and Conover were casually dating. Their relationship became more official later that summer.

Credit: Courtesy of Kristin Cavallari/Instagram

June 2021

The True Comfort author visited Conover and Kroll in Charleston, sharing a photo outside of an oyster restaurant via Instagram. “Charmed I’m sure,” she captioned the group snap.

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July 2021

Cavallari took to Instagram to clear up her relationship status, declaring that she was “single” despite rumors to the contrary. “Normally, I don’t comment on this stuff. However, these rumors have been going on for about a year now,” she said via her Instagram Story, noting that some people were claiming that she’s “involved in a love triangle, which is not true.”

“I haven’t been involved in a love triangle since I was in high school,” she said, referencing her relationship with teenage boyfriend Stephen Colletti and former classmate Lauren Conrad, which fans saw on Laguna Beach in the early 2000s. “My one and only love triangle was documented in high school.”

The entrepreneur further explained that she was in a platonic relationship with both Kroll and Conover, who were the two men in question. “I’ve never dated either one of them. I can guarantee that I’m not going to date either one of them,” she concluded.

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October 2021

Us confirmed that Conover and DeSorbo were “officially together” after months of speculation. “Their friendship turned into a relationship as they’ve spent more time together in recent weeks,” an insider told Us, two months before the New York native made her romance with Conover Instagram official.

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January 2022

The Delaware native claimed during the January 31 episode of Summer House that he and Cavallari had been intimate. During the show, which was filmed in July 2021, Lindsay Hubbard revealed that it was Conover and not Kroll who allegedly hooked up with Cavallari after sparking a friendship nearly one year prior.

Conover, for his part, shared his side of the story to DeSorbo while in the Hamptons, saying, “I’ve hooked up with her before.” He added that Kroll “hates that I was making out [with Kristin],” seemingly confirming that he and Cavallari were more than just friends at one point.

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January 2022

"I knew about the Kristin thing because I was with Craig on the 4th of July. So I knew about it,” Luke Gulbranson exclusively told Us after the Summer House episode filmed that weekend aired. “I didn't know how things were gonna go down.”

He added: “It wasn't my place to say anything, but apparently all this stuff happened. I heard about it, but I didn't hear about it until after the fact."

Credit: Courtesy of Kristin Cavallari/Instagram

February 2022

“He’s making it up — it’s not true,” a source close to Cavallari exclusively told Us after the Summer House episode aired. “They never hooked up.” The Little James founder thinks Conover is “just capitalizing on her name,” per the insider.

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February 2022

During the February 14 episode of Summer House — which taped in July 2021 — DeSorbo revealed details of Conover’s alleged messages with Cavallari.

“I guess she texted him like, ‘You are not going to make me look like an idiot with her.’ And like, ‘If you want her, like, go have her. Just don’t make me look stupid,’” DeSorbo claimed. 

Conover then called out Cavallari's post about never being in a love triangle with him and Kroll, per DeSorbo: “And he was like, ‘OK, but you went on Instagram and lied.’ Like, ‘You can’t say you were never going to date either of us. We f—ked.'" 

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March 2022

Despite Cavallari’s dating denial, Conover is insistent that he and the Hills alum “had a great relationship.” However, he told E! News that he “thought it was really, really unfair that she was thrown into a show that she's not on" after Cavallari was dragged into drama on Summer House earlier in the year. "It's one thing to be on that show and be fair game yourself, but to bring outside people and do it, I think, was just unfair. I felt terrible for her,” he added.

The Bravo personality pointed the finger at Hubbard, claiming that his alleged hookup with Cavallari was already common knowledge with their friend group. "Lindsay did it for TV,” Conover insisted. “Everyone in our lives knew about that."

Conover added that Hubbard is “not in my life anymore,” explaining that it was “not based off” her exposing his alleged romance but based on other factors. “I don't hold a lot of grudges,” he added. [I’m] really happy in the place that I'm in and I really like to lift people up, so I'm never gonna actively go after someone or try to tear them down."