Since their split in April 2020, Kristin Cavallari and Jay Cutler have not held back when it comes to their separate journeys to get back into the dating scene. In August 2021, Cutler detailed the way dating has 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 during an episode of his “Uncut With Jay Cutler” podcast. Meanwhile, Cavallari decided to go on a dating break in 2025. “I was intentional about it because leading up to the podcast tour, I didn’t want any distractions,”...

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