And the drama continues. During a Feb. 9 appearance on Austen Kroll and Craig Conover’s Pillows and Beer podcast, Kristin Cavallari hinted Madison LeCroy wanted Jay Cutler on Southern Charm. “By the way, not naming names, someone on your show was repeatedly asking my soon-to-be ex-husband to come on your show over and over and over,” Cavallari told the podcast hosts and LeCroy’s Southern Charm cast-mates. “This girl just wants me to be seen with her.”
Now, she did not verbatim name LeCroy. Buuuuuuut there’s a good chance that’s who she was talking about.
ICYMI: This is only the latest installment in what has been an ongoing saga involving LeCroy, Cavallari, and Cutler. Cutler and LeCroy were first romantically linked in January 2021, just a month after Cavallari was spotted partying with LeCroy’s ex Kroll and his pal Conover (she made it clear they were just friends, despite rumors something more was going on between her and Kroll). “It’s nothing serious at this point,” a source reportedly told Us Weekly of LeCroy and Cutler’s rumored relationship on Jan. 8. “But they’re having fun getting to know each other.”
Things took a turn for the worse on Jan. 22 when LeCroy did what turned out to be a very controversial Instagram Live. During the Live, LeCroy was seen making fun of the way Cavallari was dancing with Kroll the night they partied with each other. She was then heard insulting Cavallari’s parenting and, per BuzzFeed, reportedly "jokingly shouted Jay’s name as though he was in the house."
The next day, Cutler and Cavallari legitimately broke the internet when they shared matching Instagram posts seemingly reacting to LeCroy’s live from the night before.
"The world is full of users," they wrote alongside a picture of themselves posing side-by-side. "10 years. Can’t break that."
LeCroy tried to get involved in the comments section multiple times, but wasn’t able to get any sort of reaction from Cutler or Cavallari.
Yes, there’s still more. On Jan. 23, LeCroy defended herself by sharing some reported "receipts" featuring her conversations with Cutler. In the first, Cutler was reportedly initiating the fling by telling LeCroy he’d purchased tickets to come see her in Charleston.
In the second, which seemed to be more recent, Cutler seemed to be upset with LeCroy for using his name publicly and disparaging his family in some way (the screenshot was cut off, so it’s kind of hard to tell).
She then wrapped things up by posting a shot of herself and Cutler dressed in matching camouflage outfits alongside the caption, "too bad it didn’t work out."
So, yeah. It’s been pretty messy. And I guess somewhere along the way there’s a chance she might have tried to get him to come on Southern Charm?
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