“I Hate Johnny”- Kristin Cavallari’s Cringeworthy Onstage Reunion with Her First Love Ends in Total Humiliation

Kristin Cavallari’s Cringeworthy Onstage Reunion with Her First Love Ends in Total Humiliation—“I Hate Johnny”

She thought it would be a sweet full-circle moment. Instead, it turned into a brutal public takedown that left Kristin fuming backstage—and ready to shut the door on her exes for good.

By Gossip Maven | June 12, 2025

Kristin Cavallari was expecting nostalgia, butterflies, maybe a few laughs. Instead, she got blindsided.

In a moment meant to be heartwarming and perhaps even a little healing, the 38-year-old Laguna Beach alum invited her very first boyfriend, Johnny from Chicago, to join her live podcast taping on her “Honestly Cavallari: The Headline Tour.” What unfolded onstage was anything but sweet. It was awkward, antagonistic, and deeply personal—and it all played out in front of a live audience.

And Kristin? She was pissed.

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Young Love, Revisited… and Regretted

“He was my first,” Kristin revealed in her confessional. “We were 13 and 14, crazy in love. You never forget your first love, and I thought this would be a really cool, full-circle moment.”

Johnny, the once-adoring poet who left handwritten verses on her window, was scheduled to make a surprise appearance during Kristin’s Chicago stop. They hadn’t seen each other in 15 years. According to Kristin, Johnny was nervous—he’s not in the public eye and had never done anything like this before. So she gave him the questions ahead of time. She thought she was being considerate. What she didn’t realize? He came loaded, locked, and ready to throw verbal grenades.

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Johnny Takes the Stage—And Blows It All Up

From the jump, something was off.

Kristin, beaming and nostalgic, told the audience about how Johnny used to write her poems and leave them at her window. But Johnny cut in, correcting her—bluntly.

"You’d wake up next to me,” he interrupted. “That’s the podcast version.”

The crowd fell silent. Kristin looked thrown. But Johnny wasn’t done. "You used to greet me in outfits like this. I saw you come out in this, and it’s hard."

Yikes.

Kristin tried to laugh it off, but the energy had shifted. Then Johnny hit her with the bombshell: that she had allegedly cheated on him with his best friend—someone named Tommy.

"You broke my heart,” he said. “You hooked up with my best friend."

Kristin was floored. “I don’t even remember Tommy!” she exclaimed. “I hooked up with Tommy?!”

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Backstage Fallout: “I Hate Johnny”

The fallout was swift—and savage.

Kristin’s hurt quickly turned to fury. “Johnny is a massive letdown,” she admitted in a confessional after the show. “He was the only one I gave the questions to beforehand because he doesn’t do this. So to me, it just feels premeditated. Like he came to tear me down.”

Kristin said she had always held her memories of Johnny in a special place. “Those memories are now completely ruined,” she said bitterly.

And when she finally got offstage? The gloves were off.

“You wanna trash me in front of my f--king audience?” she raged to BFF Justin Anderson the next day. “It’s f--ked up! I hate Johnny.”

But then came the kicker—Johnny texted her after the show.

"'You were amazing last night,’" he wrote. "'Thanks for such a fun escape from reality… you’re gonna absolutely crush the rest of your tour.'"

Gaslight much?

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Same Script, Different Ex

Kristin thought this was a one-off disaster. Then came Talan Torriero.

Yes, that Talan. Her on-and-off flame from the Laguna Beach days who also joined her for a podcast appearance—and pulled similar antics.

“I actually don’t even care about looking like an idiot in front of the audience,” Kristin later said. “This is a much bigger thing for me. It’s the theme of my whole life. No guy has ever taken accountability. Ever.”

For Kristin, this wasn’t about a couple of bad nights. It was the final nail in the coffin of a pattern that stretched back decades.

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Kristin’s Long, Rocky Road of Romance

Kristin’s dating history reads like a highlight reel of early 2000s tabloid royalty—and it’s been just as dramatic behind the scenes.

• Stephen Colletti: Her first love (on camera, at least). Their turbulent relationship with Lauren Conrad caught the world’s attention—and made MTV history.

• Talan Torriero: The Laguna Lothario who apparently never stopped being chaotic.

• Matt Leinart: The USC golden boy and future NFL quarterback who Kristin briefly dated.

• Brody Jenner: A fake Hills romance—except they actually dated before filming.

• Nick Zano: Her serious boyfriend who earned a tattoo—then a breakup.

• Miguel Medina: The MTV cameraman she dated in secret while pretending to be with Brody.

• Jay Cutler: The father of her three kids, and the man behind one of her life’s most difficult (but empowering) decisions—her divorce.

• Jeff Dye: The rebound comic who claimed they “didn’t even really date.”

• Chase Rice & Morgan Wallen: Country singers with wildly different energies—Chase was casual, Morgan was “a great f--k buddy,” according to Kristin.

• Mark Estes: Her Gen Z TikTok boyfriend who was “the best”—until their 13-year age gap became too much.

• Nate Thompson: The most recent of her flings—deep, but doomed.

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Lessons Learned—and Men Canceled

“I’ve allowed these men into my life,” Kristin reflected. “And I can see it a mile away now.”

It’s a tough pill to swallow—realizing that even your most cherished memories can be tainted by people who haven’t grown like you have. But for Kristin, the awkwardness and the heartbreak seem to have crystallized into something powerful.

Clarity.

“I just know long-term [Johnny] was never right for me,” she said. “But the fact that I let him back into my space—even for one night—that’s on me. And it won’t happen again.”

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The Next Chapter: Solo, Sober, and Strong

Kristin may have walked away from her Headline Tour stop in Chicago humiliated, but she also walked away with her eyes open.

And now? She's done playing nice with the ghosts of boyfriends past.

Catch the next episode of Honestly Cavallari: The Headline Tour Wednesdays at 10 p.m. on E!—because if Kristin’s past is messy, her future looks fierce.