Kristin Cavallari left stunned as her first boyfriend makes crass jibe about their sex life during their reunion

Kristin Cavallari has explained how her public reunion with her first love went sour.

Amongst the notable relationships of the 38-year-old ex-MTV celebrity, one stands out – her longtime high school romance with Stephen Colletti. However, it’s worth mentioning that she also had a relationship with a boy she dated in middle school, named Johnny.

In the latest episode of E!’s Honestly Cavallari: The Headline Tour, Kristin shared that she plans to introduce Johnny, her first boyfriend from Chicago. She mentioned him a few times on her podcast before, stating that they were deeply in love at the ages of 13 and 14.

Although she held warm recollections of their connection, her former boyfriend from childhood viewed their relationship differently, often describing it merely as a sexual encounter.

Cavallari shared with the live crowd, “Every morning, I’d find poems on my window.

However, Johnny countered by saying: ‘In reality, upon waking up, you’d find yourself beside me. To clarify, you would indeed greet me while dressed exactly as you are currently. It was seeing you emerge in this attire that has proved challenging for me.’

In Wednesday’s broadcast, she disclosed that Johnny felt ‘anxious’ regarding his upcoming appearance before a live crowd, so she proactively gave him the questions she intended to pose as a consideration.

The mother of three stated that it’s quite distressing for those who don’t do it, so she appreciates him taking action.

Furthermore, the charming blonde shared her creative process behind including her ex-boyfriend as part of the tour’s lineup.

In her private comments during the episode, she acknowledged that Johnny was already planning to attend the Chicago event. Hearing this made her think, “This could be quite enjoyable.” We all know how hard it can be to move on from a first love. I often ponder if I’ve perhaps altered my perspective of those times over the years. Gaining his viewpoint will certainly be fascinating.

Instead of understating the extent of their relationship, Johnny further alleged that the celebrity was involved romantically with his buddy.

Johnny didn’t just minimize their connection; he also claimed the star had been dating his pal.

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Rather than denying their closeness, Johnny insinuated a romantic involvement between the star and his friend.

Before your departure, you had been exploring Barrington, Illinois, he mentioned. Unfortunately, it was a blow to me since I discovered you were romantically involved with my close friend, Tommy.

Previously known Laguna Beach cast member retorted, “I can’t recall Tommy at all. Hook up with Tommy?!

She shared her feelings of disillusionment during a post-performance interview, stating that ‘Johnny fell short of expectations. It’s truly saddening because for so long I have valued our bond with Johnny so highly. But when he appeared on stage, he was someone completely different.’

Cavallari highlighted that he had exclusively shared the questions with him prior, as it was evident that he wasn’t accustomed to such tasks.

As a lifestyle advisor, I can confidently express that his anticipation of my words left me feeling as if our encounter was intentionally planned to belittle me. My cherished memories with Johnny, forged over the years, now seem utterly tarnished and destroyed.

Kristin continued to reel over the shocking, blindsided interaction the following day.

She expressed her anger to her friend Justin Anderson, saying, “You’re trying to humiliate me in front of everyone? This is despicable! It’s truly reprehensible. I can’t stand Johnny.

Even more confusing, she said that Johnny followed up the tour appearance with a gushing text.

She announced, “You were fantastic last night!” To which she added, “Thank you for providing an entertaining escape from everyday life. It was truly enjoyable. I have no doubt that you will continue to excel in the remainder of your tour.

Another former flame, Talan Torriero, joined her on tour, along with other Laguna Beach classmates.

Unfortunately, she had a similar experience with Torriero. 

Her encounters led her to scrutinize closely the recurring trends in the romantic partners she selects.

She openly admitted to Justin that she didn’t mind appearing foolish in front of everyone.

For me, this issue is significantly important and forms the core of my existence. In contrast to Talon, it seemed commonplace or anticipated. However, with Johnny, it felt extraordinary – more like, “Wow, I can’t believe someone’s taking responsibility for their actions.” No man has ever done that in my life before.

Kristin and Jay Cutler were wed in 2013, but they parted ways in 2020. Their divorce became official in June 2022.

They share sons Camden, 12, Jaxon, 11, and daughter Saylor, nine. 

The founder of The Uncommon James has been transparent about ending a relationship with a person she describes as having narcissistic traits, which is her father.

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2025-06-14 00:52