Kristin Cavallari & Stephen Colletti's Relationship Timeline Is Sweet

Originally Published: 
Jesse Grant/Getty Images Entertainment/Getty Images

If you still associate Hilary Duff's "Come Clean" with Laguna Beach, then you're likely familiar with the saga of Kristin and Stephen. Fans have been trying to follow Kristin Cavallari and Stephen Colletti's relationship timeline ever since Laguna Beach debuted on MTV in September 2004, even though their relationship predates the reality series. And despite the fact the two have been dunzo (as Cavallari would say) for over 15 years, fans still think the iconic 2000s couple might rekindle their romance — especially since Cavallari posted a pic of her and Colletti together on Instagram in August 2020.

In the pic, the high school sweethearts are hugging and — because an eagle-eyed fan noticed Cavallari is wearing jewelry from her Uncommon James collection — the photo doesn't appear to be a throwback. Cavallari shared the picture just about three months after she and her hubby of seven years, retired NFL player Jay Cutler, announced their decision to divorce, so the timing has fans like 😮. To make things even more sus, Cutler deleted his own IG page just a day after Cavallari posted her pic with Colletti, though a source for Us Weekly reportedly claimed Cavallari and Colletti have "always been friends." Let's review how the relationship between the Laguna Beach lovers has evolved over the years.

They Dated On & Off In High School
J. Merritt/FilmMagic/Getty Images

Cavallari began dating Colletti when she was a sophomore at Laguna Beach High School and he was a junior, according to E! The first season of Laguna Beach began filming in the spring of 2004, after they'd been dating for at least a year. Cavallari was finishing up her junior year of high school and Colletti his senior year.

Over the summer of 2004, Cavallari and Colletti found themselves in a love triangle with Lauren "LC" Conrad, which caused them to constantly break up and make up. At the end of Season 1, Colletti left for San Francisco State University. The two tried to make a long-distance relationship work, but they fizzled out before winter break. In Season 2, Colletti tried to win Cavallari back and nearly succeeded on Valentine's Day in 2005... but Cavallari decided they were better off as friends.

They Attended Conrad's Fashion Show In March 2008
Jesse Grant/Getty Images Entertainment/Getty Images

Nearly three years after Cavallari decided they were dunzo for good, she and Colletti made an appearance at the Mercedes-Benz Spring 2008 Fashion Week in March 2008, where Conrad debuted her first fashion collection. Considering they took a pic together, Cavallari and Colletti were likely on good terms by then. Apparently, Cavallari and Conrad had also put the past behind them. "Me and Lauren have been cool for a long time, and I'm really proud of her and wanted to support her today," Cavallari told Us Weekly at the time.

Cavallari Posted A Throwback Pic In February 2016

About a month before her 2016 memoir — Balancing in Heels: My Journey to Health, Happiness and Making It All Work — published, Cavallari posted a throwback pic of her and Colletti on Instagram. "Flipping through #BalancingInHeels is a little trip down memory lane. We were babies!" she captioned the pic.

In Balancing in Heels, Cavallari offered some insight into what happened behind the scenes on Laguna Beach. According to her, the show's producers purposefully drove a wedge between her and Colletti. "One of the most hurtful things [the producers] did was pressure Stephen to spend time with another girl from the show, Lauren, while he and I were dating," she wrote. She said her relationship with Colletti suffered because of the contrived LC drama. "What Stephen and I had together was real, and that's what made me get through the producers' attempt at manipulating us," she added.

They Flirted On Instagram In July 2018

In July 2018, Cavallari took to Instagram to share a video of herself fooling around with a walkie-talkie while filming an episode of Very Cavallari. In the video, she says, "Hello, Stephen, this is Kristin. Stephen for Kristin." Someone off camera corrects her, saying, "It's the other way around — Kristin for Stephen." Colletti later responded to the video in the comments section, simply writing, "Go for Stephen."

Soon after their Insta interaction, Us Weekly asked Colletti if he would ever be open to appearing on Very Cavallari. "I was actually just texting with [Cavallari] the other day about something. And she was giving me a hard time. She was like, 'You've got to come on the show,'" Colletti said. He also said he still loved Cavallari "dearly," adding, "...I'll speak with Cavallari from time to time. We always just check in and say hello."

They Reunited In August 2020

In August 2020 — just a few months after announcing her decision to divorce from Jay Culter — Cavallari posted a current-day picture of her and Colletti hugging, which she captioned, "2004 or 2020?!" According to TMZ, Cavallari was in Laguna Beach, California to visit Colletti and their fellow Laguna Beach alum Alex Murrel, but sadly, sources for TMZ reportedly claimed the exes are just friends.

It doesn't sound like Cavallari and Colletti have any plans to rekindle their high school romance, but a girl can dream, right?

This article was originally published on