A Timeline of Kristin Cavallari, Jay Cutler and Madison LeCroy’s Drama

Another day, another Hollywood feud to unravel! This time, Jay Cutler and his estranged wife, Kristin Cavallari, and Southern Charm‘s Madison LeCroy are wrapped up in some serious drama.

It all started when Jay, 37, and Kristin, 34, who announced their split in April 2020, posted identical Instagram photos on Saturday, January 23. “The world is full of users. 10 years. Can’t break that,” the proud coparents of kids Camden, Jaxon and Saylor wrote.

At first, the pair’s followers were confused about the cryptic message. “OMG what’s the tea, girl!!!!!!” Jesse Tyler Ferguson‘s husband, Justin Mikita, commented. While it still remains unclear who exactly Kristin and Jay’s post was directed at, hours later, Madison, 30, stirred the pot.

The Bravolebrity and the former football player sparked romance rumors earlier this month. “It’s nothing serious at this point,” a source told Us Weekly on January 8. “But they’re having fun getting to know each other.”

After Jay and Kristin’s reunion, Madison shared a sexy bikini photo on Instagram with the caption “unbothered.” The South Carolina native also tagged her location as “Nunya Business.” Summer House star Lindsey Hubbard then commented, “I’m confused,” to which Madison replied, “Call me, sis, and I’ll tell you,” along with, “Can’t wait to clear this up.”

By Sunday, January 24, things definitely intensified! “It looks to me like I’m going to have to drop some receipts. I hate to do that, but …,” Madison said in a video clip before sharing two alleged text conversations with Jay.

In the first photo, the possible flames seemed to be coordinating a time to hang out. However, in the second set of texts, Jay seemingly called out Madison for her appearance on Watch What Happens Live with Andy Cohen on January 7.

During the interview, Andy, 52, brought up Kristin’s rumored romance with Madison’s ex and castmate Austen Kroll. The Laguna Beach alum and the Southern Charm personality partied together in December 2020 — and Kristin posted plenty of fun videos of the events on social media.

“Did you watch their adventures on Instagram?” Andy asked Madison. “I was busy having my own adventure, but no, I did not,” she replied. When the longtime host asked if those “adventures” were with Jay, she said she’s “not kissing and telling.”

Scroll through the gallery below to see a timeline of Kristin Cavallari, Jay Cutler and Madison LeCroy’s drama.