Kristin Cavallari Reunites with Her 8th Grade Boyfriend 'Who I Lost My Virginity to' During Podcast Tour: 'I Was Really Let Down'

Kristin Cavallari is going back in time.

During a recent stop on her Let’s Be Honest podcast tour the Laguna Beach alum, 38, welcomed an unexpected guest to the stage — her middle school boyfriend, Johnny.

In her March 25 recap episode, she explained that she lost her virginity to him in the 8th grade, and the reunion brought up memories that made her reflect on the other men she welcomed into her life after him.

"It was a very impactful relationship in my life, and one that I've sort of held in this high regard all of these years and really looked at it as being really sweet and loving and just I've just always walked away with really good feelings about it,” she shared. “And mind you, leading up to it, Johnny and I had been talking. We reconnected, and we were talking for a few weeks, and he asked me the questions beforehand. Because he doesn't do this stuff normally. I gave him the questions. I was like, I get it, he's probably gonna be nervous, and I wanna make him comfortable and set him up for success.”

“So Johnny comes up on stage, I'm so excited, and it was the complete opposite of how I had envisioned it going,” she continued. “I felt like he was nervous, and so because he was nervous, how he decided to channel that was to essentially give me a hard time and put me on blast. And it really threw me. It was not what I expected. I was really let down.”

She then teased that viewers will get to see the full segment in her upcoming reality series Honestly Cavallari: The Headline Tour, which is set to air on E! this summer, but noted that the interaction left her feeling “bummed.”

“It was a very different person on stage from the person I had been talking to weeks leading up to it,” she admitted. “And then the person who afterwards wanted to hang out and came up and gave me the biggest kiss on the cheek and was back to being so sweet and so kind. And what both of those instances did, was stirred up a lot of emotion about the guys that I've chosen in my life.”

She added: “Johnny on its own — I think I would have still been upset, maybe not to the degree that I was. Also being tired and it just being a long day and just giving so much energy, I was really upset. I think what it did was it made me realize how far I've come, and I'm talking specifically about guys.”

The next day, Cavallari said that she “cried” to her friends about it because “I’ve never understood why the men in my life publicly have always wanted to put me down.”

“That's been a really s--- feeling,” the reality star confessed. “Here's the thing, that's not on them. I'm enough. I love myself. And instead of giving that 'love' to these other random people, I'm gonna just start giving it to myself. And so I was talking to a couple guys while I was on tour, and I decided, I'm done. Clean slate.  I'm starting fresh because they're not my future. And I've decided I'm gonna be really serious about who I let into my life now.”

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In the past, fans have seen Cavallari’s relationship ups and downs with ex-husband Jay Cutler, which played out on her previous reality show Very Cavallari. They divorced in 2022 after nine years of marriage and three children together.

Most recently, she dated social media influencer Mark Estes. Cavallari has been open about going on dating apps since their breakup in September 2024, but now she said she is rethinking that decision.

“Even getting back on Raya, I was entertaining these conversations that were just, again, for what?” Cavallari contemplated. “For these little dopamine hits? I mean, I think now I'm gonna just start pouring all of that back into myself. And again, when the right guy comes, he'll come. But I'm not gonna worry about it."