From Stephen Colletti to Brody Jenner, Kristin Cavallari Has Dated Some a-Listers

From Stephen Colletti to Brody Jenner, Kristin Cavallari Has Dated Some a-Listers

Kristin Cavallari's dating history is major news after rumors have been swirling that she and stand-up comedian Jeff Dye are an item.

If you’re a superfan of MTV’s hit show The Hills, chances are you’ve been keeping up with Kristin Cavallari. We all know her for being dubbed as a “maneater” and famously feuding with Lauren Conrad. Kristin has been in and out of the tabloids over the years, and the main focus has always been her dating life.

While her dating history first started on Laguna Beach: The Real Orange County with Stephen Colletti, she has had her share of star-studded relationships with a slew of men. While some romances were more drama-filled than others, they have made quite the conversation pieces for fans of the star. From rumored fake relationships to making things official with a tattoo, Kristin's love life is just as interesting as you could imagine. Keep reading to get all the deets. 

Kristin first dated Stephen back in her high school days in Laguna Beach.

If you think back to the drama that took over the small town in Orange County, Kristin and Stephen's relationship was a big chunk of it all. While there is no doubt that they made a gorgeous couple, the love triangle between them and Lauren was pretty intense. 

If you remember, Kristin and Stephen's issues in their relationship stemmed from his friendship with Lauren. Kristin felt that Lauren was trying to move in on Stephen whenever they would have a falling out and it didn't help that Stephen was clearly going back and forth between the two ladies. 

However, despite the drama with rumors of infidelity, Kristin and Stephen remained solid once he graduated. But things came to an end as Kristin wanted to be single during her senior year. Thankfully, they still remain close friends to this day.

Once Stephen left for San Francisco, Kristin started dating former NFL star Matt Leinart.

While Stephen was devastated that his relationship with Kristin was over, it didn't put a stop to her dating life. After all, you can always count on Kristin to have a new boy toy in rotation. And on Season 2 of Laguna Beach: The Real Orange County, viewers heard a lot about Matt —especially since Stephen was upset about her new relationship.

According to ET, "Matt turned out to be Matt Leinart, USC's star quarterback who would go on to play in the NFL." Small world! Kristin frequently used to talk on the show about how hot Matt was and how happy that she was no longer with Stephen.

And naturally, viewers wanted to see Matt make an appearance on the show. However, the time never came. See, the pair eventually split after dating for a few months.

Chloe Bennett
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Chloe Bennett

Chloe Bennett explores the intersection of pop culture, streaming entertainment, digital trends, and contemporary lifestyle. Her weekly commentary reaches thousands of culture enthusiasts.