Kristen Cavallari and Jay Cutler on dating after a breakup

Since breaking up in April 2020, Christine Cavallari and Jay Cutler They didn’t hold back when it came to their solo journey back into the dating scene.

In August 2021, Cutler detailed how his dating approach had changed since he was last single.

“The whole landscape has changed. There are apps, there’s Twitter, there’s Instagram, it’s a whole different ball game,” he explained on an episode of the “Uncut With Jay Cutler” podcast.

Meanwhile, Cavallari decided to take a break from dating in 2025.

“I did it on purpose because I didn’t want any distractions before the podcast tour,” she explained on “Let’s Be Honest” in October 2025. “And then, honestly, it was fine, I was just in a mode of wanting to be alone and focus on work and my kids.”

Scroll down to see everything Cutler and Cavallari had to say about dating: