Kristin Cavallari Reveals She Went on a Couple of Dates With Jay Cutler After Divorce

Over a year after Kristin Cavallari and Jay Cutler filed for divorce, the Laguna Beach alum is revealing what happened after they reunited for "a couple dates.”

By Elyse Dupre Oct 20, 2021 2:57 PMTags
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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.'"

Kristin Cavallari and Jay Cutler: Romance Rewind

Cutler and Cavallari share three kids together: Camden Jack, 9, Jaxon Wyatt, 7, and Saylor James, 5.

"I come from divorced parents and I was like, 'I don't want my kids growing up thinking that this is a good relationship,'" the Uncommon James founder added. "Because I got to see my mom remarry and be in a good relationship so that I knew what one was. I mean, I wanted my kids to see me happy. I just did. And they're better off. And they've adjusted really well, not that there's ever a perfect age for it, but they were at good ages. And so, I'm glad that it happened when it did."


So where do her and Cutler stand? When Bristowe asked if they're still friends, Cavallari reiterated "it's a rollercoaster." She also admitted co-parenting isn't easy.

"This is what I said to my friends," she said. "I'm like, 'If I didn't have kids with Jay, I would never talk to him ever again. But now, I have to talk to him a lot.'"

Cavallari and Cutler are both moving on. She even said she'd be open to getting married again one day if the right person came along.

"I know I will. I'm in no rush whatsoever though," she wrote in a recent Instagram Q&A. "I'm really enjoying being alone right now. I've done the work I've needed to do for the past year and a half and I'm finally getting to a place of potentially being ready for a relationship but not quite yet." 

E! News has reached out to Cutler's rep for comment but has yet to hear back.