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.
“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.”
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: