Kristin Cavallari‘s blast from the past did not turn out like she had hoped.
During the June 11 episode of “Honestly Cavallari: The Headline Tour,” a former student from Laguna Beach met up with her first boyfriend, but their reunion didn’t turn out smoothly.
In a candid moment, I found myself reminiscing during my podcast session here in Illinois. You see, I’m planning to reconnect with Johnny, my first love from Chicago – a relationship that dates back to our teenage years. Our affection was as profound as any young hearts could experience at 13 and 14. I’ve mentioned him on the podcast a few times before, recalling those tender moments of adolescent love.
Thirty-eight-year-old individual observed that Johnny seemed apprehensive because he is not typically in the spotlight, and it had been fifteen years since their last encounter.
Kristin remarked, “For those who don’t engage in this activity, it can be quite distressing. Therefore, I am grateful he took the initiative.
Plus, the reality star thought it would be fun to catch up with the man she lost her virginity to.
She clarified in a private moment, “Johnny was already planning to attend the Chicago concert, which made me pause and think, ‘This could be quite exciting.’ It’s no secret that moving on from your first love can be tough. And I often ponder if I’ve somehow rewritten our story in my mind over the years. Hearing his perspective will be fascinating.
However, when Johnny eventually took the stage, the interaction turned out to be more confrontational than Kristin had anticipated.
After Kristin shared their relationship with the audience, she mentioned finding poems on her window upon waking up each day. In response, Johnny provided a different memory. “Instead of discovering poems, you would find me beside you,” he said. “But for our podcast listeners, that’s not quite accurate. What actually happened was that you would greet me every morning dressed exactly like this. It’s a bit overwhelming because I remember seeing you step out in this outfit, and it’s tough.
Man, that off-kilter remark really threw me for a loop, but things were about to get even more uncomfortable. Then, here I was, being publicly accused by Johnny, as if I had eyes straying left and right!
…”As you departed, it was Barrington, Illinois where you were tasting life,” he continued. “Unfortunately, your actions left me shattered as you developed feelings for my close companion, Tommy.
Startled, Kristin refuted the statement, countering with, “I can’t recall Tommy at all.” Caught off guard, she exclaimed, “Did I date/hang out with Tommy?!
To put it simply, I couldn’t help but feel a pang of disappointment when I saw Johnny attempting to cast the blame on me in our relationship. It was clear as day that he was trying to paint me in a negative light.
Johnny was disappointing, his mother sadly admitted in private. For so long, she had valued their relationship greatly. But when he appeared on stage, he was unrecognizable compared to the person she knew before.
She went on to explain, “I only shared the questions with him ahead of time since I knew he wasn’t familiar with this kind of task. However, it seemed like he was already prepared for my responses, making me feel that his actions were planned, intended to undermine me. The fond memories I’ve built over the years with Johnny are now tainted and spoiled.
The next day, Kristin was still fuming over the uncomfortable interaction.
She angrily exclaimed to her friend Justin Anderson, “You’re trying to insult me in front of my entire audience? That’s low! It’s truly disrespectful. I can’t stand Johnny.”
In a fit of anger, she told her buddy Justin Anderson, “You’re trying to belittle me in front of everyone here? That’s despicable! It’s really unfair. I can’t stand Johnny.”
Both versions convey the same meaning while being more polite and suitable for general audiences.
A calmer Kristin then revealed the surprising text she received from Johnny after the show.
Last night, you truly shone,” I told Justin, reading aloud. “Your performance provided an exhilarating respite from everyday life – it was just what I needed. I have no doubt you’ll continue to excel and conquer the rest of your tour without a hitch.
Following another live performance where her ex-co-star from Laguna Beach, Talan Torriero, repeated such behavior, Kristin decided to cut ties with the men of her past.
She openly confessed to Justin that her current situation meant more to her than worrying about appearing foolish before the crowd. Instead, this topic seemed pivotal in her life’s journey. With Talan, it was almost as if she expected such an outcome. But when it came to Johnny, it felt like a surprising revelation – no man had ever accepted responsibility for their actions in her entire life.
Now, Kristin no longer entertains that type of behavior from men.
She mused, “I’ve welcomed these men into my world, and it’s clear to me now, it’s like seeing a distant landmark. It’s a pleasant realization of the path I’ve traveled.
Catch Kristin’s tour as “Honestly Cavallari: The Headline Tour” unfolds on TopMob, starting this Wednesday at 10 p.m.
In the meantime, keep reading to look back at Kristin’s star-studded dating history.
The first love you never forget, especially when television cameras are capturing every up and down in the tumultuous relationship. The public was privy to Kristin Cavallari and Stephen Colletti’s romantic tale unfold on ‘Laguna Beach’ for two seasons, as this couple, who started dating a year before filming began, along with Lauren Conrad, created one of television’s memorable love triangles.
Kristin expressed in her 2016 book, Balancing in Heels, that she had a deep affection for Stephen and put forth great effort to maintain their relationship. What began as a high school romance transformed into the central plot of a highly popular television series. To Kristin, Stephen was the most valuable aspect of her life, and she had no greater concern. She disliked arguing with him on screen because it felt like exposing all their private disagreements.
Despite their romantic relationship not surviving past high school, they’ve managed to stay friends. At one point, Kristin even mentioned to TopMob News that Jay could possibly appear on her show, ‘Very Cavallari’.
In 2022, Talan Torriero, a well-known character from Laguna Beach, shared insights with TopMob News. He revealed that although the LC-Stephen-KCav love triangle was the main focus, there were numerous other compelling storylines unfolding off-camera. This included Kristin and even Lauren, as Lauren had relationships outside of high school with intriguing individuals who preferred to stay out of the spotlight or were only briefly featured on the show.
Regarding my dynamic relationship with Kristin, I must confess that our connection had its roots even before the show premiered. In fact, there were established relationships or casual encounters taking place, if you will. My bond with Lauren didn’t start until much later, during my second season or so. As for Kristin, we went through an on-and-off relationship during her junior and senior years.
In the opening episode of Laguna‘s second season, Stephen feels heartbroken upon discovering that Kristin has started dating a man named Matt from USC, following his departure for college.
Turned out, the individual at USC was none other than Matt Leinart, their renowned football quarterback, who later played in the NFL. However, contrary to popular belief, Matt never made an appearance on MTV’s hit show and his relationship with Kristin did not last long.
In 2008, there was speculation about a possible reunion between Kristin and Matt after they were seen together in Las Vegas, but it was never confirmed that they reconciled officially.
In the later seasons of The Hills, Kristin and Brody Jenner appeared to be in a romantic relationship for show purposes. However, it’s worth noting that they actually dated years before that, shortly after Kristin’s stint on Laguna Beach ended, having been introduced by Talan during that time.
She shared back in 2012 on Bethenny that she dated Brody when she was 18, and interestingly, this was just after Laguna Beach. However, during The Hills, they portrayed us as dating for several episodes.
After being in an on-again, off-again relationship for nearly a year, the duo finally ended things officially in 2006. She shared with People magazine that it was challenging due to her busy work schedule, but they remained good friends despite their breakup.
In the beginning of 2006, Kristin and Nick Lachey, known for being a member of 98 Degrees, ignited rumors of a romantic involvement. This came a year after his well-publicized separation from Jessica Simpson, who was then his wife.
At that point in time, Kristin dismissed the speculations and clarified to People magazine, “There’s no story here, nothing is happening. He’s a good person, but I must stress that we are simply friends.
Initially, she claimed to be avoiding the unexpected, intensely bright focus on her, but later confessed it was merely an attempt to evade it.
She stated that it was an extraordinary period in her life as she suddenly became the center of attention, finding herself on the front page of every gossip magazine, which she discussed during a November 2024 episode of her “Let’s Be Honest” podcast. Everywhere she went, there were photographers lurking around, waiting outside her home to capture her actions.
Following the conclusion of his “Newlyweds” chapter alongside Jessica, she remarked, “This was quite the sensation in 2006,” she continued. “Quite an exhilarating journey.
Not long after her relationship with Brody ended, Kristin started seeing Nick Zano, a well-recognized actor from the WB sitcom “What I Like About You”.
The relationship between them was quite intense; Kristin, in fact, got his initials inked on her wrist as a symbol of their bond.
But when the pair called it quits in December 2007, Kristin had the tattoo removed.
As Kristin pretended to be in relationships with Brody and Justin Bobby Brescia for the camera, she was secretly seeing someone off-screen during her tenure on The Hills.
Back in 2010, I found myself navigating a private romance with MTV cameraman Miguel Medina. Even my fellow cast members Heidi Montag and Audrina Patridge were unaware of our secret relationship.
For several months, we kept our relationship hidden, but it was only later that she disclosed this to her ex-colleagues during an episode of Very Cavallari. Intriguingly, while I was shown dating Brody on the program, Miguel was secretly filming our romance.
Later, she explained that their relationship had become public during the final stages of their professional collaboration due to the fact that paparazzi photographed them at the airport a week prior to concluding the series, which ultimately led to them being discovered.
Following her breakup with Miguel, Kristin attracted the attention of NFL player Jay Cutler who was a quarterback for the Chicago Bears at the time. Just a year into their relationship, Jay made a significant move by proposing in 2011. However, the couple’s romance did not last long as Kristin ended the relationship a few months afterwards. She wrote in her book “Balancing In Heels” that some adjustments were needed.
After carefully setting up Xs and Os, the couple welcomed their son Camden in August 2012, tied the knot in June 2013, and expanded their family by having son Jaxon in May 2014 and daughter Saylor in November 2015. Despite appearing to be a strong team, Kristin has shared insights about their team dynamics following their public announcement of divorce in April 2020.
In an interview for The School of Greatness podcast in 2022, she shared that the most daunting experience in her life was going through a divorce. However, despite its frightening nature, it turned out to be the most beneficial decision she’s ever made, serving as a catalyst for her self-discovery and personal growth journey focused on self-love.
After her divorce from Jay, Kristin initially sought humor with the Los Angeles-based comedian Jeff Dye. However, even though they said those three significant words during a January 2021 Instagram Live session, “It wasn’t a serious relationship from the start,” according to a source who spoke to TopMob News in March. Kristin was just enjoying herself.
In a public statement made in November 2024, the comedian admitted that they did not have a serious relationship. However, he acknowledged that she had led him to believe there was a possibility. He compared their interactions to treating him like a pet puppy.
As of August 2021, I’ve stumbled upon a fresh duet partner in the country music scene with Chase Rice. Currently, it’s all quite casual between us, as we’re still exploring this new connection. I’ve attended one of his concerts and we’re enjoying the journey together so far.
However, after several weeks had passed, it seemed that the Nashville locals were indulging in solo performances, as Kristin stated on Instagram, “At present, I am not involved in any romantic relationship.
In late 2024, a specific part of Kristin’s romantic history was revealed – her brief involvement with the country artist Morgan Wallen.
On the December episode of Bunnie XO’s Dumb Blonde podcast, Kristin remarked, “He was an excellent choice for a casual partner. He excelled in that area.
And he’s got some smooth moves out of the bedroom as well.
On our initial date, he truly exhibited chivalry, and he mentioned, “I’ll come to get you, I’ll choose the location,” in a confident manner, taking care of everything. Later, after we left the venue, “He kissed me in the rain,” she disclosed, “and it was such a tender moment.
Despite Kristin labeling Mark Estes as her “best boyfriend” on TikTok, she candidly admitted that the significant 13-year age difference between them was a challenge for her.
She explained on her podcast in October 2024 that she parted ways with Mark as she felt, in the long run, it wasn’t suitable. She clarified this wasn’t due to a lack of love or any negative incidents; neither cheating nor harsh behavior occurred. Instead, they simply didn’t do anything wrong. She noted that these types of breakups are often the most challenging, she believed.
In essence, she stated, “In the end, I believe he should live through various life experiences because he’s still young. I can feel my age a bit more now due to life experiences. If you look back at when I was 24, so much has transpired for me since then. Those years are crucial and formative; they help shape who you become. This is the time when one discovers themselves, and he needs that opportunity.
In an update several months later, Kristin clarified that the retired sportsman she hinted at dating during her earlier interviews was indeed the ex-NHL player she mentioned on her podcast in April 2025.
She stated that he is an individual who has invested significant effort in self-improvement, and our bond reached an extraordinarily profound depth. In her words, this romance represents one of the most introspective relationships I have experienced.
That very afternoon, I took the opportunity to discuss our connection on my podcast, Energy Line, expressing sentiments much like those of Kristin’s glowing appreciation.
He enthusiastically agreed she was great company, mentioning they had an enjoyable time together. However, he lamented that despite their compatibility, circumstances simply didn’t allow for their relationship to continue.
Watch a brand new episode of Honestly Cavallari: The Headline Tour Wednesdays at 10 p.m. on TopMob.
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2025-06-12 06:17