Let's just be real for a second. In the world of reality TV crossovers, nothing—and I mean nothing—stressed out the Bravo-sphere quite like the Nashville-meets-Charleston entanglement of Kristin Cavallari and Craig Conover. It was the crossover nobody saw coming, mostly because we were all too busy looking at Austen Kroll.
For years, the story was basically a riddle. Was it a love triangle? A PR stunt? A drunken mistake? We finally got some actual answers in 2025 during Kristin’s podcast tour, Honestly Cavallari, and honestly, the reality is way more awkward than the rumors.
The Night in Nashville That Started It All
It’s 2020. Everyone is bored, stuck inside, and scrolling. Suddenly, a video pops up on Instagram of Kristin Cavallari, Austen Kroll, and Craig Conover dancing in a kitchen to Taylor Swift’s "We Are Never Ever Getting Back Together." Kristin is on Austen’s shoulders. The internet, predictably, lost its collective mind.
At the time, Kristin was fresh off her divorce from Jay Cutler. The media immediately pegged her and Austen as a thing. But here’s the kicker: while everyone was watching Austen, it was actually Craig Conover who was the "romantic" interest. Or, as Kristin later put it on Watch What Happens Live, they were "romantic for two seconds."
That "two seconds" comment is vintage Cavallari—blunt, a little dismissive, and totally chaotic.
The Timeline Crossover: Kristin, Craig, and Paige
The biggest point of contention has always been the overlap. Did Craig hook up with Kristin while he was starting things up with Paige DeSorbo? If you ask Kristin, the answer is a pretty firm probably.
✨ Don't miss: How Tall is Rory Calhoun? Why the Western Legend’s Height Still Matters
She’s gone on record saying she saw a photo of Craig and Paige in New York City—the very first public photo of them together—and immediately pulled the plug. She literally texted him and said, "Hey, let’s just be friends." She didn't want to be the third wheel in a brewing Bravo romance.
What happened on the 2025 Podcast Tour?
During her stop in Boston for the Honestly Cavallari tour, she finally cornered Craig on stage. It was... tense. Craig, ever the "charming" Southern gentleman, tried to downplay the overlap. He claimed that once he and Paige decided to be monogamous, he stopped talking to Kristin.
But Kristin wasn't having it. She actually tried to read their old text messages on stage to prove her point. Craig apparently had a "hot mic" moment afterward where he was caught saying the whole thing was the "dumbest thing" he’d ever done. He was clearly rattled.
- The "Two Seconds" Hookup: Kristin admits it was a brief, drunken dalliance.
- The Paige Factor: Kristin claims she bowed out the moment she saw Craig with Paige.
- The Lie: Kristin flat-out told Craig on her tour, "You did lie to me."
Why This Drama Still Matters in 2026
You might wonder why we're still talking about a hookup from years ago. It’s because it changed how Kristin Cavallari handles her public life. She called the whole Southern Charm era a "wake-up call."
Being a mom of three, she hated that her name was being used for "scandalous headlines" on shows she wasn't even on. She felt like the "boys" (Craig and Austen) were fueling the fire for their own storylines on Southern Charm and Summer House. It made her "reel things in" and become much more private about who she’s actually dating.
Separating Fact from Bravo Fiction
There are a lot of misconceptions here. Let's clear the air on what actually happened versus what the fans made up.
First, Kristin and Austen Kroll were never a thing. They are just friends. The "humping his neck" video was just drunk fun. Second, Craig and Kristin’s "relationship" was never a relationship. It was a few hangouts and a kiss (or two).
👉 See also: Why the Miley Cyrus Naked Scene in Wrecking Ball Changed Pop Culture Forever
Craig’s history of "embellishing" the truth is well-documented—even Paige has joked about him being a compulsive exaggerator. So when Craig says there was "no overlap," and Kristin says there was, most fans tend to side with the woman who has the receipts in her iCloud.
The Aftermath
As of 2026, the dust has mostly settled. Craig and Paige eventually split in late 2024, and Craig is currently back on the dating apps (Raya, specifically). Kristin has moved on to other ventures and has made it very clear that she and Craig are strictly friends now.
Actually, during that same tour, Craig admitted that if he hadn't been dating someone else at the time, he probably would have kissed her on stage. Old habits die hard, I guess.
What You Can Learn From This Mess
If you're following the drama for more than just the tea, there are a few real-world takeaways here:
- Trust the "Gut" Check: Kristin saw a red flag (the Paige photo) and exited immediately. She didn't wait for a formal breakup or a confirmation. If it feels messy, it usually is.
- Privacy is a Choice: After this, Kristin stopped posting her "guy friends" as much. If you value your peace, keep the "drunk dancing" videos off the grid.
- Receipts are Forever: In 2026, your "he said, she said" is easily debunked by a screenshot. Be careful what you text.
To get the full perspective, you should go back and listen to the June 2025 episodes of the Let's Be Honest podcast. Hearing the tone of Craig’s voice when he gets caught in a timeline gap tells you more than any tabloid headline ever could.
👉 See also: The Met Gala Jack Schlossberg Non-Invite: What Really Happened Behind the Scenes
Check your sources, watch the old WWHL clips, and remember that in the world of reality TV, "just friends" usually has a footnote.
Next Steps: You can actually stream the full Honestly Cavallari: The Headline Tour on Peacock to see the unedited tension between Kristin and Craig for yourself. It's the "Boston" episode you're looking for.