Looks like Southern Charm and Very Cavallari had more crossover drama than fans ever imagined. Kristin Cavallari just confirmed the long-swirling rumors — something did, in fact, go down between her ex-husband Jay Cutler and Southern Charm’s Madison LeCroy.
On the June 4 episode of Watch What Happens Live, host Andy Cohen went straight for the juicy stuff, asking Cavallari if anything happened between Jay and Madison.
Her answer? A firm “Yes!” followed by, “Imagine if cameras were up then.”
Uh… excuse us while we process that bombshell.
Fellow guest Amanda Batula chimed in with a laugh, saying, “Crossovers are crazy.” Honestly? She’s not wrong.
A Quick Recap of the Chaos
Back in 2020, the world was dealing with lockdowns, but in the celeb world, things were heating up. Kristin and Jay announced they were splitting after seven years of marriage. In a joint statement, they said it was a case of “two people growing apart,” and promised to co-parent their three kids — Camden (12), Jaxon (11), and Saylor (9) — with love and respect.
Then came the Bravo world twist.
Kristin started casually hanging out with Southern Charm stars Austen Kroll and Craig Conover — much to the internet’s delight. At the time, Austen had just broken up with Madison LeCroy, and suddenly everyone was watching these two reality TV worlds collide.
But the real twist? Madison was also linked to Jay Cutler shortly after.
Flirty DMs & IG Shade
In early 2021, sources said Madison and Jay had a “new, flirty thing” going on — nothing serious, but definitely something. LeCroy even threw some shade Kristin’s way on Instagram Live, which didn’t go unnoticed.
Jay clapped back with an Instagram post that seemed to show solidarity with Kristin, writing:
“The world is full of users. 10 years. Can’t break that.”
Cryptic? Sure. But the message was loud and clear.
Ultimately, Jay and Madison’s spark fizzled. He’s now engaged to Samantha Robertson, and Madison married Brett Randle.
Where Things Stand Now
Today, everyone seems to have moved on. Kristin says she actually knew Samantha before Jay got with her, which made things easier to accept.
“I could sort of envision their dynamic,” she shared during the June 4 premiere of her new Honestly Cavallari: The Podcast Tour, in a chat with Kim Zolciak-Biermann.
She’s also openly supportive of Jay’s relationship and remains focused on co-parenting their kids. Maturity goals, honestly.
So, yes — Kristin just confirmed what fans had always suspected: there was something going on with Jay and Madison. It may be in the past, but the drama? Timeless.