Kristin Cavallari is 38 now. She's a mogul, a mom of three, and honestly, the most interesting person to come out of the MTV reality boom. But let’s be real. When people search for "Kristin Cavallari ex-boyfriend," they aren't looking for a Wikipedia list of names from 2005. They want to know what happened with the TikTok guy. They want the tea on why her marriage to Jay Cutler still makes headlines six years after the split.
Dating in your 30s is a mess for everyone. Doing it while being the face of Uncommon James and raising three kids in Nashville? That's a different level of chaotic.
The Mark Estes Era: More Than Just a "TikTok Cowboy"
The internet basically exploded in February 2024 when Kristin went "hard launch" with Mark Estes. If you aren't familiar, Mark is one of the "Montana Boyz"—a group of guys who got famous on TikTok for wearing flannels and looking rugged in the woods. He was 24. She was 37.
People were judgmental. They called it a midlife crisis. But if you listen to her podcast, Let’s Be Honest, she tells a different story.
Mark wasn't just some fling. She actually called him the "best boyfriend" she’s ever had. That’s a massive statement considering she was married to an NFL quarterback for a decade. He was sweet. He played basketball with her sons, Camden and Jaxon. He was present.
Why did they break up?
They split in September 2024 after seven months. It wasn't because of cheating. It wasn't because of some blow-up fight. Kristin basically said she had to be the "grown-up" and let him go so he could actually live his life.
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Think about it. At 24, Kristin was just starting her marriage journey. Mark hasn't even had his "real life" years yet. She knew that long-term, he’d want his own kids and a different trajectory. She chose to break her own heart to give him a chance at a future that didn't involve being a stepdad in a fishbowl. It’s kinda selfless when you think about it.
Jay Cutler: The Ex-Husband and the "Trauma Bond"
You can't talk about a Kristin Cavallari ex-boyfriend or partner without talking about Jay Cutler. Their 10-year relationship is the shadow that hangs over everything she does.
By early 2026, the dust has somewhat settled, but the drama is never truly gone. They’ve been divorced since 2020, yet they still make news for things like "phone usage" for their kids. Recently, Kristin admitted on the Dumb Blonde podcast that she and Jay actually tried to date again after the divorce was filed.
She called it a "trauma bond."
- They went on a few secret dates.
- They tried to see if the spark was still there.
- She realized she was just repeating patterns she had with her own father.
- Eventually, she had to cut it off for the 18th millionth time (her words, not mine).
Today, they are in a better place. They sat together at their son's basketball game recently. For anyone who watched Very Cavallari, that feels like a miracle.
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The Mystery "Big Deal" Coach and Recent Flings
Since Mark Estes, Kristin has been a lot more selective. She had a very brief thing with retired NHL player Nate Thompson in early 2025, but that fizzled out by March because she "just didn't want to be in a relationship."
Then came the "Big Deal Coach."
In October 2025, Kristin revealed she went on a date with a professional sports coach. Her agent set it up. He flew to Nashville. He was a "really, really good guy." But the spark? Non-existent.
Fans on Reddit have been losing their minds trying to figure out who it was. The leading theory is Will Hardy of the Utah Jazz, mostly because he’s young-ish and fits the "big deal" description, but Kristin is keeping that name in the vault. She’s learned that once you give the public a name, you can't take it back.
The "WAG" Curse and Moving Forward
Kristin joke-calls herself a "WAG through and through." Athletes are her kryptonite. From Matt Leinart in high school to Jay Cutler to potential coaches, she clearly has a type.
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But honestly? Her 2026 vibe is different. She’s leaning into being single. She’s talked openly about her "dry spells" and how she’d rather be alone than with the wrong person. It’s a shift from the girl we saw on The Hills who always needed a plotline.
If you're looking for the "next" Kristin Cavallari ex-boyfriend, you might be waiting a while. She’s currently prioritizing her peace over another headline-grabbing romance.
What to Watch for Next
If you're following her journey, keep an eye on her podcast. It’s where she drops the real info before the tabloids can spin it. The most important takeaway from her recent dating history isn't the names—it's the fact that she's finally comfortable being the one who ends things when they don't serve her.
Practical Takeaways from Kristin's Dating Playbook:
- Audit your patterns: If you keep dating the same "type" (like her athletes), ask if it's actually working.
- The "Age Gap" Reality: It's fine for a season, but life stages matter for the long haul.
- Co-parenting isn't a straight line: It took her four years to be able to sit next to Jay at a game. Patience is required.
- Listen to your body: If a date is "perfect" on paper but your body feels tense, it’s a no.
The biggest lesson? Sometimes being "done with the dating scene" is the most productive thing you can do for your own mental health.