In April 2020, Cavallari and Cutler announced their decision to part ways after nearly seven years of marriage.
“We have nothing but love and respect for one another and are deeply grateful for the years shared, memories made, and the children we are so proud of. This is just the situation of two people growing apart,” the pair wrote in a joint statement via Instagram.
As Cavallari and Cutler focused on coparenting their three children, Camden, Jaxon and Saylor, they both offered a glimpse at their attempts to move on. In August 2021, the former Chicago Bears quarterback 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,” Cutler explained during an episode of his “Uncut With Jay Cutler” podcast. “You’re not just walking into a restaurant or bar and talking to somebody. That doesn’t exist anymore.”
Cavallari, however, later revealed that the estranged pair initially attempted to give their relationship one last try. “Jay and I actually went on a couple of dates, like, months and months and months ago,” the Hills alum shared on the “Off the Vine” podcast in October 2021. “But then I was, like, it’s not there for me anymore.”
For the reality star, the attempt to try again gave her the reassurance she needed about calling it quits for good.
“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,” she added. “And so I just decided I didn’t want to be in a toxic relationship anymore and I had to break it off.”
At the time, Cavallari also reflected on the realization that she is interested in narcissistic men. “So I’m, like, ‘OK I am breaking this f–king cycle. What is this?'” the former Laguna Beach star, who briefly dated Chase Rice after her split from Cutler, said.
In April 2022, the Uncommon James founder elaborated on the person she would like to see herself with. “Someone who is so comfortable in their own skin who is stable and has their own s–t going on. I want a good, sweet guy,” she wrote during an Instagram Q&A. “I’m done with narcissist a–holes thank you very much.”
That same month, a source exclusively told Us Weekly that Cutler was still holding out hope for a reconciliation.
“Jay is still very much hung up on Kristin,” an insider revealed. “He still has a lot of love for her and wishes things weren’t as they are. They are coparenting well — he just wishes they were still together. He deeply cares about her.”
Scroll down for everything the former couple have said about their individual attempts to start dating: