Kristin Cavallari Slams Reunion With First Boyfriend For 'Premeditated' Answers: 'Massive Letdown'

During the June 11 episode of her new series, Honestly Cavallari: The Headline Tour, the 38-year-old invites her first love -- 8th grade boyfriend Johnny, the person she lost her virginity to, up on stage -- and it proved to be very awkward.

"I'm going to be pulling up Johnny, my very first boyfriend from Chicago," Kristin explained during a confessional before one of her live shows in Illinois. "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."

She revealed that he was "nervous" about being a guest since he isn't in the public eye and they hadn't seen each other in 15 years.

"For people who don't do this, it's f--king nerve-wracking," Kristin added. "So, I even appreciate him getting up."

"Johnny was actually coming to the Chicago show anyway," she elaborated in a confessional

"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," she added.

The theme of the show was people who have been on Cavallari's podcast, Let's Be Honest, before so Johnny sat down alongside reality star Harry Jowsey, who has been a guest on the podcast.

Cavallari joked that Johnny looked "the exact same" as when they were in eighth grade.

She said that she was heartbroken by their split as kids which led to her being a "heartbreaker."

"I was known as being the heartbreaker because I never wanted to feel that ever again," she explained. "Johnny was impactful for me."

However, it looked like Johnny had a different version of the story.

After Kristin told the audience of their relationship, "I would wake up in the morning and I would have poems on my window," Johnny interrupted, alleging their relationship was more physical: "You'd wake up next to me. That's the podcast version," he said. "To be clear, you would actually greet me in outfits just like this. I saw you come out in this and it's hard."

Cavallari then tried to take hold of the conversation by bringing up how Johnny "hooked up" with her best friend as soon as they broke up. However, Johnny said it was the other way around.

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

"I don't even remember Tommy," she quipped back in shock. "I hooked up with Tommy?!"

Johnny didn't stop there, he said Cavallari was "always a heartbreaker."

When the show ended, it was clear Cavallari was disappointed with Johnny's behavior on stage in front of thousands of people.

"Johnny is a massive letdown. It honestly breaks my heart because for all of these years, I have held my relationship with Johnny in this high regard," she shared. "Then he got up on stage and he was a completely different person."

She continued: "He was the only person that I gave the questions to beforehand because obviously he doesn’t do this stuff. 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 of Johnny -- all of these years now -- he just completely ruined."

Cavallari opened up about how Johnny's behavior was a constant theme with men in her life.

"It just gets to a point where I’m so sick of men trying to just beat me down," she said while getting emotional after the show.

Johnny was not actually supposed to be on the show. The Hills alum had to find a replacement for her ex-boyfriend Mark Estes, who puled out last minute.

Cavallari claimed Estes decided not to do it when he found out he'd be sharing the stage with Jowsey.

"My ex boyfriend Mark Estes originally agreed to be on my second episode, as well as Harry Jowsey from Too Hot to Handle," she explained. "But, Talan [Torriero from Laguna Beach] decided to group text message on Instagram both Harry and Mark."

"Mark had no idea that Harry was coming," Cavallari revealed. "It was a huge blow to his ego and he's not coming now." So she had no choice but to replace the Montana Boyz TikToker

Later in the episode, Cavallari revealed that Estes had still been reaching out to her. "Last night, during the show, Mark texted me, 'How's everything going?'" she told her friends. "And then he just texted me, 'I miss you.'"

The reality star and the TikToker previously dated for seven months but broke up in the fall, partly due to their 13-year age gap.