Quote from Oladosun Joshua Segun on June 12, 2025, 8:28 AM

Kristin Cavallari had an uncomfortable reunion with her first boyfriend, Johnny, during a live show for her podcast Honestly Cavallari: The Headline Tour. Initially, she thought it would be a nostalgic and meaningful experience, as Johnny was her first love when they were teenagers. However, when he joined her on stage, things quickly turned sour.

"I'm going to be pulling up Johnny, my very first boyfriend from Chicago," Before one of her live Let us Be Honest podcast shows in Illinois, Kristin gave an explanation during a confessional. "I've talked about him a couple times on the podcast. We were as in love as you could be at the tender age of 13 and 14."

The 38-year-old observed that because Johnny is not in the spotlight and they have not seen one another in 15 years, he was "nervous" about being a guest.

"It is f--king nerve-wracking for individuals who do not do this," Kristin continued. "So, I am even grateful that he got up."

The reality star also believed that reuniting with the man she lost her virginity to would be enjoyable.

"Johnny was actually coming to the Chicago show anyway," In a confessional, she went into further detail. "I was like, 'Wait a minute, this could be really fun.' We all know how it is to get over your first love, it's very difficult. And I do wonder if I've sort of, like, changed the narrative in my mind all these years. To have his perspective is gonna be awesome."

However, the confrontation was more aggressive than Kristin had anticipated when Johnny was eventually hauled up on stage.

Following Kristin's explanation of their relationship to the audience, "I would wake up in the morning and I would have poems on my window," Then Johnny broke in with another memory. "You'd wake up next to me. That's the podcast version," he shot back. "To be clear, you would actually greet me in outfits just like this. I saw you come out in this and it's hard."

Johnny made remarks that threw Kristin off, including implying a different version of their relationship history and accusing her of having cheated with his best friend—a claim Kristin adamantly denied. She was visibly frustrated that Johnny seemed intent on making her look bad in front of her audience. Afterward, she expressed disappointment, saying the interaction ruined her cherished memories of their relationship.

"Before you left, you were sampling Barrington, [Ill.]," he continued. "You broke my heart actually because you hooked up with my best friend Tommy."

Kristin, who has refuted the claim, was astonished. "I don't even remember Tommy," she fired back. "I hooked up with Tommy?!"

"Johnny is a massive letdown," in a confessional, the mother of three bemoaned. "It honestly breaks my heart because for all of these years I have held my relationship with Johnny in this high regard. And then he got up on stage and he was a completely different person."

"He was the only person I gave the questions to beforehand because obviously he doesn't do this stuff.," she went on. "He knew exactly what I was going to say, so, to me, it just feels premeditated, like he wanted to come out there and tear me down. These memories that I've had with Johnny all of these years are now just completely ruined. "

Kristin was still upset about the awkward encounter the next day.

"You wanna trash me in front of my f--king audience?" she yelled at her best friend, Justin Anderson. "It's f--ked up! It's really f--ked up. I hate Johnny."

Despite Kristin’s frustration, Johnny later sent her a supportive message, thanking her for a fun escape and complimenting her performance. However, the experience ultimately served as a reminder to Kristin of how far she has come in her personal growth and boundaries with past relationships.

"'You were amazing last night,'" she read to Justin. "'Thanks for such a fun escape from reality, definitely needed that. You're gonna absolutely crush the rest of your tour. No doubt about it.'"

Additionally, Kristin was done with the men from her past after Talan Torriero, her former boyfriend and costar from Laguna Beach, performed a similar act during another live performance.

"I actually don't even care about looking like an idiot in front of the audience," she told Justin. "This is a much bigger thing for me. It's the theme of my whole life. With Talan, it's like, 'Okay, it's expected.' Then Johnny, it was like, 'Oh my god!' Like, no guy has ever taken accountability in my life, ever."

Kristin no longer puts up with males acting in that way.

"I've allowed these men into my life, and I can see it a mile away now," she pondered. "It's a nice reminder of how far I've come."