October 2021
The Little James founder called her split from Cutler the “brightest and the saddest” part of her life during an appearance on the “Off the Vine” podcast. “It’s probably the best decision I’ve ever made but it’s had really sad moments,” Cavallari said. “There’s been times over the last 18 months where I’m like, ‘Is this the right decision?’”
The reality TV star revealed that after separating from the former football player in April 2020 the estranged pair tried to give things another shot. “Jay and I actually went on a couple of dates, like, months and months and months ago,” she explained. “But then I was, like, it’s not there for me anymore.”
Cavallari added: “The thing with Jay is, we aren’t getting our divorce because of love lost, which made it really challenging because we were crazy about each other. And so I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off. But then going back and dating him a little bit made me reaffirm it, like, ‘No, I know that I’m doing the right decision.’”
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