See Kristin Cavallari and Stephen Colletti’s Relationship Timeline From ‘Laguna Beach’ to Today

If you were a teenager in the mid-2000s, there’s a solid chance you were extremely invested in Kristin Cavallari and Stephen Colletti’s relationship. The former Laguna Beach costars pretty much set the bar for what young love on reality television looks like to this day — a.k.a. drama and love triangles galore.

In September 2004, the first episode of Laguna Beach, “A Black & White Affair,” aired on MTV and set the scene for Kristin and Stephen’s romance. From the beginning, it was clear that costar Lauren “LC” Conrad, who was supposedly just Stephen’s best friend, was going to cause some major friction between them.

Throughout the series, Kristin and Stephen broke up on several occasions. While they were broken up, they’d always try to make each other mad by hooking up with other people. For Stephen, it was always Lauren. For Kristin, it was a handful of other cast members — including Talan Torriero

Kristin Cavallari and Stephen Colletti Relationship Timeline
Jen Lowery/Startraksphoto.com

At the end of season 1, Stephen left for college at San Francisco State University, but not before he and Kristin share a teary-eyed goodbye on the beach. At the time, it seemed like the high school sweethearts were going to make things work long-distance.

In July 2005, season 2 of Laguna Beach aired and Kristin took over Lauren’s job as the official narrator. In the first episode, “Since You’ve Been Gone,” last year’s seniors returned from college for winter break. Stephen attempted to rekindle things with Kristin while he was home for the holidays, but she wanted nothing to do with him.

Later, in episode 7, “I Hate Valentine’s Day,” Stephen tried once again to win back Kristin’s affections and for a little while, it worked. In episode 11, “Lies and Goodbyes,” Kristin finally visited Stephen in San Francisco, where he proceeded to pull out all the stops with a romantic dinner and firework show.

Sadly, Kristin made it clear she just wanted to be friends and that was the end of her relationship with Stephen for good … or was it? Nowadays, the former flames both appear to be single. 

The Uncommon James designer split from husband Jay Cutler in April 2020 and the One Tree Hill actor seemingly hasn’t had a girlfriend since Chelsea Kane in 2013.

To see a complete timeline of Kristin Cavallari and Stephen Colletti’s relationship, scroll through the gallery below.