Kristin Cavallari Went on a Few Dates With Jay Cutler After Divorce

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Kristin Cavallari is coming clean about life after her divorce from Jay Cutler

“I have to say, it’s been such a rollercoaster,” she told Kaitlyn Bristowe on the Oct. 19 episode of Off the Vine, “but it’s been the brightest and the saddest, the whole experience.” 

Cavallari, 34, and Cutler, 38, filed for divorce in April 2020. And while the Laguna Beach alum said it was “probably the best decision I’ve ever made,” she also acknowledged there’s been “really sad moments” and that she at times questioned if they made the right move. 

“Jay and I actually went on a couple dates, like, months and months and months ago,” she shared. “But we did.” 

Ultimately, she realized that same connection “wasn’t there anymore.” 

“The thing with Jay and I is we aren’t getting a divorce because of love lost, which made it really challenging because we were crazy about each other,” the reality star continued. “And so I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off. But that’s made it hard and made me sit here and question it for a few months. But then going back and dating him a little bit made me reaffirm, like, ‘No, I know that I’m doing the right decision.'”