Before Jay Cutler: A Look Back at Kristin Cavallari’s Love Life

Jay Cutler and Kristin Cavallari

Jay Cutler and Kristin Cavallari | Jeff Schear/Getty Images for Michigan Avenue Magazine

Kristin Cavallari has given love a try numerous times before settling down with her husband, Jay Cutler. From her on-screen relationships to her rumored hookup with an A-lister, she’s had quite the love life leading up to marriage. Here’s every man Cavallari was linked to, leading up to Cutler.

Stephen Colletti

Who can forget the days of Cavallari and Stephen Colletti on Laguna Beach? The iconic teenage couple started dating when Cavallari was a sophomore in high school, but the MTV reality show began filming their lives during her junior year. Cavallari may have opened up about Laguna Beach and The Hills being scripted, but her relationship with Colletti was real.

“We loved hard and fought hard. My relationship with Stephen went from our own high school romance to the fodder of a hugely successful television show,” she wrote in her book, Balancing in Heels: My Journey to Health, Happiness, and Making It All Work.

Talan Torriero

Talan Torriero was another familiar face on Laguna Beach. He was in the friend group of the show’s main stars, and even reportedly hooked up with Cavallari in 2004.

Brody Jenner

Cavallari did actually date Brody Jenner — but not the way you thought she did. According to PopSugar, “Kristin and Brody’s relationship on the show was totally fake. Yes, even that emotional series finale scene when Kristin says goodbye to Brody before leaving town.”

In fact, Jenner was dating Playboy model Jayde Nicole the entire time he was on the show, as Cavallari spilled on Bethenny in December 2013. That means none of his TV relationships were real, from Lauren Conrad to Jen Bunney.

The only time Jenner and Cavallari really dated was before the show ever started. “I dated Brody when I was 18 right after Laguna Beach and that’s it,” she admitted. “On the show, they had us dating for a few episodes … which wasn’t real at all.”

Matt Leinart

Cavallari might now be married to a former football player, but it isn’t the first time she’s been romantically involved with an NFL star. In 2006, she dated quarterback Matt Leinart, but it didn’t last for long.

Nick Zano

Cavallari was clearly serious about her relationship with Nick Zano. So serious, in fact, that she got a tattoo on her wrist with his initials. Unfortunately, they only dated from 2006 to December 2007, so she ended up getting her tattoo removed.

Chris Evans

Chris Evans

Chris Evans | Anthony Harvey/Getty Images

Who knows if Cavallari actually hooked up with Chris Evans, but they were definitely close at one point. In 2008, The New York Post reported that she hooked up with the actor at the opening of Cabana One at the Mayfair Hotel in Miami.

Cavallari, however, insists it never happened. She told Us Weekly, “No, we’re just friends.” She added, “I’ve known Chris for awhile, just through mutual friends. I’ve known him for a few years, actually.”

Justin ‘Bobby’ Brescia

As it turns out, Cavallari’s relationship with Justin Bobby was just as fake as her relationship with Brody Jenner. As a guest on Watch What Happens Live with Andy Cohen, Cavallari spilled the beans on every lie viewers were told.

When Cohen asked Cavallari which guy she regretted dating the most, she replied, “No one. I would say Justin but I never really dated him.”

She added, “I think I made out with him once, and that took a lot of convincing. Finally I was like, ‘Alright, I’ll just do it!’”

“Fake relationships, fake fights, but it was fun, ’cause you’re acting. And that was more fun for me.”

Miguel Medina

In 2010, Cavallari stepped out with a surprising new man. She was spotted at the Los Angeles International Airport getting cuddly with none other than Miguel Medina, a cameraman from The Hills.

“They’ve been dating for a couple months,” a source told Life & Style magazine at the time. “It’s very serious.”

Jay Cutler

Finally, Cavallari began dating her forever man in 2010: now-former Chicago Bears player, Jay Cutler. By April 2011, the two were engaged and in love, but Cavallari called it off before walking down the aisle. In her book, she explained why she made the decision to end the engagement. “At that moment, something wasn’t right,” she wrote. “A few things needed to change, and I knew the only way Jay would see how serious I was, was if I ended the relationship.”

Thanks to couples therapy, their relationship was saved. They ended up resuming their plans and tying the knot in June 2013. They’re now parents to Camden, Jaxon, and Saylor, and have settled down in Nashville, Tennessee.