Kristin Cavallari Is Back on Raya 

Everyone wants to know about Kristin Cavallari’s dating life. Although she recently returned to Raya, Cavallari has been keeping things quiet for a simple reason—there isn’t much to tell. 

“Honestly, this is not the phase of my life when I want to be dating much,” Cavallari explains. “I decided I was done with dating because I did not want any distractions before my tour. I did not put any energy into men. I’m serious—I had hot ass men DMing me!” Cavallari says.

Instead, she’s been focusing her time and energy on her recent four-city Let’s Be Honest Headline Tour, which was a major success. But that hasn’t stopped the questions from rolling in.

“Eighty-five percent of the questions I get are like: ‘Can you tell me about your recent dates? What about your love life? What happened with the last guy you were dating? Did you meet any new guys on the podcast tour? What’s happening with Raya?’” she says.

Kristin Cavallari Dating Mishaps and Lessons

Her post-divorce dating history

Contrary to tabloid speculation, Cavallari set the record straight and says she has not been “hoeing it up.” She can count her post-divorce relationships on one hand: a physical trainer for about five to six months, a comedian for another six months, TikTok star Mark Estes for seven and a half months, and most recently, a brief fling with a hockey player that lasted a month.

That hockey player—which internet sleuths identified as retired hockey player Nate Thompson—was someone Cavallari initially mentioned on the Dumb Blonde show at the end of 2024, which she now regrets. But since the cat’s out of the bag, Cavallari doesn’t mind sharing. (She even talked about it on the podcast tour.)

“He is someone who has done a lot of work on himself, and we really connected on a deeper level. It was one of the deeper relationships that I’ve ever had. In a really short amount of time, we told each other everything. He is such an amazing guy, and we were firing on all cylinders, but there wasn’t any flame,” she says.

She knows exactly what she wants

After years in the dating world, Cavallari has developed a clear vision of what she’s looking for. She wants someone older than her, preferably in his 40s and with children of their own, since she’s done having kids. Cavallari also understands no relationship is perfect and requires work. But that does not deter her from looking for her definition of “perfect.”

“I understand what I am looking for is rare, and because I’m so clear on what I want and I’ve waited this long, I’m not going to put up with the bullshit I’m not going to settle for anything less than what I want,” she says.

Looking ahead, Cavallari says chemistry is non-negotiable: “That attraction piece has to be so on fire for me to date someone. I need to—in the beginning—to want to rip your fucking clothes off,” she laughs. 

She also wants someone who pushes her outside of her comfort zone and to be better. “I want a dynamic where we are both learning how to be better people, and we pick up each other’s flaws. I want a real partnership,” she says. 

“It’s about truly letting someone into your whole inner world and being 100 percent yourself and really vulnerable. That’s what I want, even though it’s scary for me,” she says.

Making up for lost dating time

When it comes to questions about why she has seemingly dated a lot in recent years, Cavallari has no problem explaining it: “I’ve always been in a relationship—from eighth grade until five years ago. The last five years have been my dating phase, which I realize most people go through in their 20s. But I met my ex-husband at 23 and had my first kid at 25.”

Now, she’s approaching dating with a newfound sense of self-worth that comes with maturity: “I have gone through this incredible growth period that has forced me to learn self-love.” 

She does not see any of her exes as a mistake. With every one-off date or every relationship, Cavallari sees them as necessary steps toward understanding what she wants in a future partner. “I am really learning about myself. The last five years have been research to learn what I do and do not want. I’m really happy on my own—I don’t need to be in a relationship,” she says.