Showing people how it is done. Since their split, Kristin Cavallari and Jay Cutler have not held back when it comes to their separate journeys to get back into the dating scene.
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.”
The Indiana native, who has been linked to Jana Kramer and Madison LeCroy, noted that there are “aspects that have to be taken into consideration” as he attempts to start seeing new people.
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.”
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Scroll down for everything the former couple have said about their individual attempts to start dating:
After being linked to comedian Jeff Dye, Cavallari opened up about dating someone new amid her divorce. "That was the moment. I was having fun, you know? It was like, I also want to go out in public as well," she said during the "Scrubbing In" podcast. "[Jay and I] filed over a year ago, and then it took me a minute, but then I dated somebody, and it was great. He was the perfect guy to date after Jay. He was really sweet, made me feel really good. But now I just want to be by myself. And when it's the time, it'll happen. I'm not gonna force it." Rob Latour/Shutterstock
While reflecting on online dating, Cutler admitted that it was "hard as hell" for him to find someone new. "Meeting people is hard. I think finding out what people really want from you, I think that's probably an issue," he said during his "Uncut With Jay Cutler" podcast. "I'm at a different phase of my life now with kids. It isn't just a purely selfish play by my part." Mike Wulf/Cal Sport Media/Newscom/The Mega Agency
During an Instagram Q&A, Cavallari noted that she wasn't ruling out having more kids with someone in the future. “I don’t necessarily want more kids (my life feels very full — and busy! with my 3). However, if I met someone who didn't have kids, I would consider it,” she shared at the time. ABC/WDTV
The Very Cavallari alum took to social media to address her love life. "You guys are so funny. This is the number one question I got. Sooo let's just start this thing off strong," she answered a dating question during an Instagram Q&A. "I've honestly needed the past 2 years to work through some heavy stuff. I dated a little here and there but no one serious. I am finally in a place where I'm ready for a relationship." The California native also teased that she was happy about what the future holds for her. "Let's just say this: when you are able to finally fully close a chapter, it's amazing what you will start to attract," she added. Stephen Greathouse/Shutterstock
During an appearance on "The Bellas Podcast," Cavallari said that she wanted to work on herself before she started dating again. "Through my divorce, I've done a lot of reflecting and I've really looked inward," she explained. "And I've really just focused on myself and making sure that I worked through everything with my ex and really closed that chapter. ... I don't know how people jump from relationship to relationship. Like, I wanna make sure I'm fully healed before entering something new. I also think just being really comfortable in your own skin and knowing who you are is really important [when] entering a relationship. So, it was important to me to just really get in touch with myself again and figure out who the hell I am now." MEGA; AP/Shutterstock
"I'm actually excited to see who I can be in a new relationship because I feel like I've done so much work the last few years," Cavallari shared during an episode of "The School of Greatness" podcast. "I'm in no rush to be in a new relationship, but when I am, it will excite me to see how different I can be." MBS/MEGA
“Since, like, March I’ve been actively dating. I was dating someone for a couple of months, but I continued to go on other dates,” Cavallari said during an appearance on the “Not Skinny, But Not Fat” podcast. “I’ve been on quite a few dates.” The True Comfort author explained that many of her dates have come from her DMs. “My DMs have essentially been my dating app,” she confessed. “I’m only going to go for the verified [accounts]. I can’t filter through all of my DMs but I can see those blue checkmarks, honey.” When it comes to what she’s looking for in a partner, Cavallari added, “I prefer someone to not be [famous]. I really, in my head, my ideal man is a businessman who no one knows. … I’m pretty picky, I guess. But I’m not going to settle, I’m going to stay picky.” Image Press Agency/NurPhoto/Shutterstock
Cavallari confessed on the "Call Her Daddy" podcast that she hopes Cutler "finds someone" to marry someday — even though "it stung a little" to see him move on after their split. "I want him happy. My kids benefit from that, you know. So I hope that he gets remarried," she said. Elsewhere in the episode, the MTV personality explained why she has a hard time ghosting after a bad date. "I'm too f--king nice," she joked. "I wouldn't want to be ghosted either. I would actually appreciate someone being like, 'Hey, you know what, you're great but didn't feel any chemistry.' Which I said that to another guy ... and his friends were making fun of me for weeks about it. ... Like, thank you for validating why the f--k I don't like you. I'm trying not to waste anyone's time." UncommonJames/DennisLeupold/MEGA; Nam Y Huh/AP/Shutterstock
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