So, Kristin Cavallari is single. Again. Honestly, if you've been following her since the days of "Laguna Beach," this feels like a familiar rhythm, but the stakes are way different now that she’s a mogul with three kids and a massive podcast.
The internet basically melted down when she went public with Mark Estes—that 24-year-old TikToker from the Montana Boyz—back in early 2024. People had opinions. The age gap was the headline, but the breakup, which went down in late 2024, actually revealed a lot more about where Kristin’s head is at these days.
The Mark Estes Era and Why It Fizzled
Let's be real: the optics were wild. Kristin was 37, and Mark was just a few years out of college. On her podcast, Let’s Be Honest, she didn't hold back. She called him the "best boyfriend" she’d ever had. They were taking trips to Greece, he was meeting her kids (Camden, Jaxon, and Saylor), and things looked—dare I say—actually stable?
But by September 2024, it was over. Kristin explained it in a way that actually makes a ton of sense if you’ve ever dated someone in a different life stage. It wasn't about a big blow-up or cheating. She basically realized that at 24, Mark needs to go live his life. He needs to figure out who he is without being "Kristin Cavallari’s boyfriend."
"I started to feel the age a little bit," she admitted. It’s that realization that while the chemistry is there—and she was very vocal about the "best sex" part—the long-term math just doesn't add up when one person is raising teenagers and the other is still figuring out their first real career move.
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What happened after the split?
- The "I Miss You" Texts: In June 2025, during her "Honestly Cavallari" live tour, she revealed that Mark was still reaching out. He even texted her "I miss you" right before a show.
- The "Big Deal" Coach: In late 2025, Kristin teased that her agent set her up on a date with a high-profile sports coach. She wouldn't name him, though the internet (specifically Reddit) went into a frenzy trying to figure out if it was Utah Jazz coach Will Hardy. She said the date was great, but the sparks weren't quite flying.
- The Country Star Connection: We can't talk about Kristin Cavallari dating without mentioning the Morgan Wallen "bomb." Just recently, in January 2026, a full interview with Bunnie XO resurfaced where Kristin detailed their past fling. He met her kids, he was a "true gentleman," and they even had a movie-moment kiss in the rain. But that's firmly in the past.
Kristin Cavallari Dating: The New Ground Rules
If you're wondering who she’s going to date next, she’s actually given us a pretty specific roadmap. She is officially "done" with the entertainment industry. No more actors.
Why? Because she wants someone who can actually show up. She mentioned Brandon Sklenar (from 1923) as a total crush, but immediately shot it down because he's an actor. "He’s going to be on set... the scheduling would be a nightmare," she said. She’s looking for a partner, not a long-distance pen pal.
She also talked about how she’s realized she was "repeating patterns" from her childhood in her marriage to Jay Cutler. It took her four years post-divorce to really untangle that "trauma bond." Now, she and Jay are finally in a place where they can sit together at their son’s basketball games without the tension being palpable. That’s huge.
The "Dry Spell" and Finding Balance
Believe it or not, the woman who spent her 20s as the "it girl" of MTV is currently embracing a slower pace. In late 2025, she actually joked about her "lack of sex" being "really sad" since the Mark Estes breakup.
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But she’s also been very clear: she doesn't need a man to fill the gaps anymore. She gets a lot of her emotional support from her best friend and hair stylist, Justin Anderson. She’s focusing on Uncommon James, her kids, and her own peace.
What Most People Get Wrong About Her Love Life
The biggest misconception is that Kristin is just "jumping from guy to guy." If you actually listen to her talk, she’s incredibly picky now. She’s looking for someone who has "depth" and someone who has their own life together.
She recently went on a date with another former athlete (her "kryptonite," as she calls it) who is in his 40s and has his own kids. That feels like the more likely lane for her in 2026. Someone who understands the chaos of carpools but still has that competitive edge she seems to crave.
How to Navigate Dating Like a "Mogul"
If there's anything to learn from Kristin's journey, it's about setting hard boundaries. She’s not afraid to end a "good" relationship (like she did with Mark) because she knows it isn't the "forever" relationship.
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Takeaways for your own dating life:
- Life stages matter. You can love someone and still recognize that you're in different chapters.
- Identify your "Type" vs. your "Needs." Kristin loves athletes, but she needs someone with a flexible enough schedule to be present.
- Do the "Dad" work. If you find yourself dating the same person over and over, look at your earlier influences. Breaking the cycle is the only way to find something healthy.
Kristin is currently "single and ready to mingle," as she told fans in an Instagram Q&A, but don't expect her to settle for just anyone. She's waiting for the "big deal" that actually sticks.
Check your own dating patterns: If you’re constantly ending up in the same "toxic" loops Kristin describes, try writing down the non-negotiables that have nothing to do with looks or status. Focus on the logistics of how a partner fits into your actual daily life.