Kristin Cavallari Admits ‘I Have Not Had Issues’ Finding Men to Date Because ‘I’ve Never Had Any Desperation’ (Exclusive)

Kristin Cavallari has skills — and she knows it.

The Hills alum, 38, sat down for the latest episode of PEOPLE’s Reality Rewatch series, where she looked back on her early years on television. In one clip from Laguna Beach, Cavallari’s high school friend told her she could have “any guy you want, any time, any place,” and she admits there is some truth to that.

“I have not had issues when it comes to men, let’s put it that way,” she laughs. “I think I’ve always had this attitude of a disassociation, almost, where I give off this energy of, ‘I don’t need you, because I’ve actually never needed a man.’ I still don’t need a man, I want a man. There’s a very big difference there.”

“And I’ve never had any sort of desperation when it comes to men,” the podcast host continues. “I have made them chase me, and honestly, it’s mostly been unintentional. But it’s just that energy of like, ‘You need me, I don’t need you.’”

Cavallari says it wasn’t hard for her to develop a chemistry with her onscreen flings because she naturally flirts.

Later, she watched a scene of her and Justin Bobby on The Hills while they were in a “fake” relationship. Despite most of the show being scripted, Cavallari explains why the dynamic still comes off as believable.

“That’s just who I am,” she admits. “I’ve always been a big flirt. I’m still a big flirt. But it’s not even intentional, it’s literally just my personality. I’m goofy, I’m fun. Like, I don’t know!”

Cavallari has had several public flings over the years, including her marriage and subsequent divorce from ex Jay Cutler.

The Uncommon James founder has always been open about her dating life since entering the spotlight in the early 2000s. She even documented parts of her often tumultuous seven-year marriage to the former NFL player, with whom she shares three children, on their reality series, Very Cavallari.

The show ran for three seasons but came to an end when she filed for divorce in 2020. She has since been linked to comedian Jeff Dye, Bravo’s Craig Conover, actor Glen Powell and country singers Chase Rice and Morgan Wallen.

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Cavallari has had more serious relationships since becoming single, but hasn’t found someone to settle down with yet.

Then, in February 2024, Cavallari hard-launched her relationship with TikTok star Mark Estes on Instagram. The pair broke up after seven months in September 2024, and she cited their 13-year age gap as one of the reasons. 

“He’s been the best boyfriend I’ve ever had,” Cavallari revealed in an October episode of her Let’s Be Honest podcast. “I just know long-term he needs to experience life, he’s young… I started to feel the age a little bit with life experience.”

More recently, she began mentioning that she was seeing a retired athlete. When she announced they were no longer together in an April podcast episode, she revealed that the mystery man was former NHL player Nate Thompson.

She also labeled their time together “the most honest, pure, amazing, quote-unquote relationship I’ve ever had,” but said she realized she “just didn’t wanna be in a relationship” at the time.