In a recent exclusive interview with Us Weekly, Kristin Cavallari opened up about her feelings regarding an uncomfortable public encounter with her first boyfriend, Johnny, during her live podcast tour, “Honestly Cavallari: The Headline Tour.” The episode, which aired on June 11, 2025, showcased a reunion that did not go as she had hoped, leaving her grappling with the implications of their past relationship.
Cavallari, now 38, expressed her disappointment in how Johnny and fellow Laguna Beach alum Talan Torriero downplayed their romantic history. “I thought it was going to go very differently than it did,” she admitted. “That was really difficult for me. The tour ended up being way more personal than I had anticipated. Way more from my past came up, and it was a great opportunity for me to realize how far I’ve come, so I’m thankful for it.”
In the episode, Cavallari confronted the awkwardness of the situation, particularly how Johnny and Talan’s remarks reduced her significant memories to mere jokes about sex. “I don’t think trust is given. I’ve always been like that. Being on TV obviously enhances that,” she noted. “I had held Johnny in this high regard for so many years. To have Talan and Johnny back-to-back diminish what we had and almost make it just purely about sex was really difficult for me.”
Cavallari reflected on her initial feelings about Johnny, recalling their youthful romance fondly. “Particularly because Johnny was my first love. We actually had a really amazing relationship for being 14,” she shared. “I literally used to wake up and find poems on my window. I was trying to give him that opportunity, and he just kept tearing it down.”
The reunion took a turn when Johnny, instead of reminiscing about their sweet moments, made comments focused on the physical aspects of their relationship. “To be clear, you would actually greet me in outfits just like this one,” he remarked, which left Cavallari feeling disheartened. “Johnny is a massive letdown. It honestly breaks my heart because for all of these years, I have held my relationship with Johnny in such high regard,” she confessed during a confessional segment.
Cavallari also pointed out that she had given Johnny the questions in advance to help him prepare for the podcast, which made his dismissive remarks feel premeditated. “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,” she said, emphasizing how the experience had tarnished her cherished memories of their relationship.
After the episode aired, Johnny sent Cavallari a message thanking her for the experience, stating, “You were amazing last night. Thanks for such a fun escape from reality. Definitely needed that. You’re gonna absolutely crush the rest of the tour. No doubt about it.” However, Cavallari’s feelings about their reunion remained complicated, as she continued to process the impact of Johnny’s comments on her self-perception and their shared history.
As she navigates her post-divorce life, Cavallari has been open about her journey of self-discovery and empowerment following her split from NFL star Jay Cutler in April 2020. The couple announced their separation after nearly seven years of marriage, and since then, Cavallari has focused on her personal growth and exploring new relationships.
In conclusion, Kristin Cavallari’s recent reflections on her live podcast tour and the unexpected reunion with Johnny highlight the complexities of past relationships and the importance of accountability in personal growth. As she continues her journey, fans can look forward to more insights and stories from Cavallari as she embraces her life as a single woman and a successful entrepreneur. “Honestly Cavallari: The Headline Tour” airs on E! Wednesdays at 10 p.m. ET, providing fans with a glimpse into her life and the lessons she has learned along the way.