Why Do Kristin Cavallari & Jay Cutler Have Drama With The Cast Of ‘Southern Charm’?

If you’re the kind of person who follows a lot of pop culture accounts on Instagram, you already know it was a busy weekend. Kourtney Kardashian is reportedly officially dating Travis Barker, Erika Jayne is apparently Armie Hammer’s neighbor, and the Gen-Z Disney Channel stars are still feuding. But all of that is just some light messiness compared to the pure chaos of whatever the f*ck is going on with Jay Cutler, Kristin Cavallari, and Southern Charm star Madison LeCroy. I realize that sounds like a 2021 pop culture Mad Lib, but this crossover is actually happening, and it’s kind of messy.

Before we really dive in, let’s set the scene and get our bearings. As you probably know, former Laguna Beach star Kristin Cavallari and former NFL quarterback Jay Cutler were married for several years before announcing their separation last spring. For the last few months, they both seemed to be living their best single lives, with rumored flings and new relationships. But then, Kristin and Jay flipped their entire relationship situation on its head on Friday night, when they posted identical photos together, which a cryptic caption that suggested they may be back together.


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A post shared by Kristin Cavallari (@kristincavallari)

With almost no context to go on, these posts obviously stirred up a million rumors, but unfortunately it looks like Kristin and Jay will be remaining tight-lipped about what’s really going on with them. So that’s where the drama ends, right? LOL, if it were, we would not be here. This is where Jesus takes the wheel and makes a complete left turn, because it’s where the Southern Charm cast comes into the picture. On the show this season, one of the main storylines has been Austen Kroll and Madison LeCroy’s struggle to fully pull the plug on their toxic relationship. They hate each other, but they love each other, and we all know how that goes.

Since Southern Charm finished filming over the summer, it seems like Austen and Madison’s breakup has become more final, but the toxic behavior between them has carried over onto social media. And somehow, aside from shady comments and #spon for Budweiser (a slight to Austen’s beer company), Kristin and Jay have become the main weapons in their Instagram war. 

In December, Austen and his castmate Craig Conover went to Nashville to hang out with Kristin and her hairstylist BFF Justin Anderson (one of the thirstiest people alive), and the entire weekend was documented on Instagram. This included an instantly classic Instagram Live, where the obviously intoxicated crew danced to Taylor Swift’s “Mean” while Kristin was on Craig’s shoulders. On a subsequent appearance on Watch What Happens Live, Austen revealed that the friendship with Kristin started when she slid into Craig’s DMs, and they all got dinner together while she was visiting Charleston. He also clarified that while they enjoy each other’s company, nothing romantic was going on. But while things stayed platonic between Kristin and the Southern Charm boys, that was apparently not the case with their respective exes, Jay and Madison. 

According to a People source, Jay “reached out to Madison” in early December, and “she flew out to see him after filming the Southern Charm reunion.” Yes, this is right around the time that Kristin was hanging out with Austen, adding another layer to this cake of confusion. Considering that Jay and Kristin are objectively more famous than Austen and Madison, this whole love-rectangle situation feels like some complex revenge equation, but it’s not clear exactly who was trying to get revenge on whom. Either way, it’s a damn mess. Though Madison was never splashing her time with Jay all over Instagram, she made comments suggesting they knew each other, and when asked about Jay in her own WWHL appearance, she coyly replied that she wasn’t “kissing and telling.”

So while there was some chatter about Madison’s possible relationship with Jay, it wasn’t until last week that she really threw her hat into the ring of messiness. In an Instagram Live on Thursday night, she and Southern Charm castmate Venita Aspen recreated Kristin and Austen’s infamous Taylor Swift IG Live, and in the same video she spoke vaguely about Austen, Kristin, and Jay. Kristin and Jay made their matching posts the next day, raising speculation that the posts were targeted at Madison. On Jay’s version of the post with Kristin this weekend, Madison commented, “I told you it would all workout [sic],” and later added that she couldn’t wait to “clear this up.”

After a day of eagerly awaiting further developments, Madison finally fired up her Instagram stories on Sunday afternoon, and she decided to drop some receipts regarding her relationship with Jay. There are two screenshots of their text conversation, one of which appears to show him trying to make arrangements to come visit her. In the other screenshot, Jay chastises Madison for bringing his name into the situation. There are no dates on the screenshots, but it seems likely that the second set of texts came after Madison spoke about Jay on Thursday’s IG Live. Madison pushes back, saying she respects him and his family, and says “if you weren’t interested in something real you shouldn’t have slept with me.” And I OOP. She followed that up with a selfie of her and Jay in hunting gear, so at the very least, we know they’ve spent some time together.

Kristin and Jay haven’t said anything about Madison’s involvement, but Kristin’s BFF Justin (the thirsty one) has had no problem speaking out. In a TikTok comment, he accused Madison of “making stuff up for attention,” and said that she’s “created all of this nonsense.” Justin posted many more similar comments, also confirming that nothing happened between Austen and Kristin, and again accusing Madison of wanting “fake TV drama.” Later on Sunday, Justin posted some more Instagram stories, where he said that posting private text messages is “f*cking low,” and that he’s only involved in this situation because he wants to stick up for his friend. 

Honestly, I kind of love the fact that Kristin and Jay dropped a bomb with their photo together, then immediately disengaged from the situation. They knew they would get their headlines and reposts, and now the real thirsty people (Justin and Madison) are left to duke it out in the social media trenches. Austen, for his part, was posting about his golf outing over the weekend, seemingly ignoring the drama completely.


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A post shared by Madison LeCroy (@madison.lecroy)

It’s unclear what’s really going on with Kristin and Jay—I have my doubts that they’re really back together. But it’s even more unclear what Madison is trying to do here. Prove to the world that Jay Cutler knows she exists? Okay, sure, mission accomplished. Maybe the texts suggest that he was the one pursuing her, and maybe he was an asshole, but nothing here is rock-solid proof. And even if they did have some kind of relationship going, did she think this technically-still-married father of three was her soulmate? If so, then maybe there is hope for my crush on Timothée Chalamet. She’s already pivoted to posting vague, shady captions on Instagram, so she’s definitely going to be milking this for a while.

And as for Justin, I understand the urge to jump in when people are talking about your friend, but I’m not sure what Madison is doing even really affects her? If anyone is unbothered by this whole situation, it’s probably Kristin. At the end of the day, everyone in this story is going to go their separate ways, and the thirsty will stay thirsty.

Images: Timothy Hiatt/Getty Images; kristincavallari, madison.lecroy / Instagram

Dylan Hafer
Dylan Hafer
Dylan Hafer has watched over 1000 episodes of Real Housewives because he has his priorities in order. Follow him on Instagram @dylanhafer and Twitter @thedylanhafer for all the memes you could ever want.