The Truth About Kristin Cavallari's New Boyfriend Jeff Dye

Wondering who Kristin Cavallari's new boyfriend Jeff Dye is? Well, first some history: Cavallari made headlines in April of 2020, when she and her partner of over ten years, Jay Cutler, announced they were getting a divorce. The reality star who first became famous in 2004, thanks to her starring role in Laguna Beach, told the world in an Instagram post, assuring her fans that the split was amicable. "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," she wrote in the caption.

With that, Kristin Cavallari's strange marriage was over. That meant that Cavallari was once again single, but she wasn't ready to mingle — that is, until six months later, when the Very Cavallari star was seen kissing a mystery man at a Chicago bar. Curious to know more about him? Read on to get the deets about Kristin Cavallari's new boyfriend Jeff Dye.

After Kristin Cavallari divorced her husband, Jay Cutler, plenty of fans wondered who the reality star would end up with next. Some speculated that she might go back to her ex-boyfriend, fellow Laguna Beach star Stephen Colletti, though TMZ cleared the air when they shared the pair were "just friends" in August of 2020.

Indeed, Cavallari wasn't seen arm in arm with anyone until October of 2020, six months after she announced her split with Cutler. That's when TMZ broke the news that she was seen smooching comedian and host Jeff Dye at a Chicago bar. While the magazine clarified that they didn't know if this was a one-time thing or the beginning of something beautiful, what's definitely evident was that Dye and Cavallari were quite fond of one another. 

We'll be keeping our eyes on their Instagram pages for any updates now that the cat is out of the bag!

Kristin Cavallari's new boyfriend Jeff Dye grew up in Seattle, a city that he calls both liberal and artistic, as well as fun to live in. The self-described late bloomer struggled in a way that might surprise you, too. "I didn't learn to read until I was about 20 years old," he confessed on an episode of The Honeydew. And while Dye was forthcoming about that fact on the podcast, it's something that he used to keep secret, as he was ashamed of it.

How, you may wonder, did Dye remain illiterate for so long? "I think it's a perfect marriage of being one, lazy, and two ... indifferent to trying to learn," he continued. He also discovered later that he's dyslexic and has ADD as well. Dye really did have the literacy odds stacked against him!

Somehow, Dye managed to coast by in school (though he never graduated), thanks to his gregarious personality. "I was really good at being silly and making everyone laugh, so kids would just... do my homework," he added. It wasn't until he was an adult that he finally learned to read.

Although Kristin Cavallari's new boyfriend Jeff Dye struggled with literacy and comprehension growing up, he was often saved by his sense of humor and comedic timing. It's not surprising, then, that Dye knew exactly what he wanted to do for a career as an adult. "I feel very blessed that I always knew I wanted to be a comedian," he shared in an interview with Moontower Comedy News. "There was never a distraction period or a time of me thinking I needed to go pursue anything." 

That's why he didn't stress out too much over his academic pursuits, instead keeping his eye on the prize. "When I got out of high school, I didn't bother with college," he continued. "I went to Giggles Comedy Club in Seattle, Washington and I just kept going to open mics." And while it took a long time to really refine his act, Dye eventually got good enough to run with the big dogs.

It's no secret that stand-up comedy isn't an easy business, as it can be difficult to master. So, like many folks when they first start out in the industry, Kristin Cavallari's new boyfriend Jeff Dye bombed on stage frequently. "I was so bad in the beginning, it was embarrassing," he confessed in a chat with Moontower Comedy News. "Also, I was very much a part of the, as they call it in comedy, the Dane Wave." Dye was referring to a group of comedians who were inspired by Dane Cook's performances when he was super hot on the comedy scene, who tried to emulate him in their acts as opposed to being original.

Things got so bad that Dye realized he had to make a change, or he was never going to make it as a comic. "One day, I was at a bookstore, and I got this comedy book Judy Carter wrote about how to formulate a joke," he continued. "I took the same ideas that were bombing, even things that got no laughs, and that night I was getting laughs by just formulating them the correct way."

Once Kristin Cavallari's new boyfriend Jeff Dye figured out how to refine his act, he kept his audiences laughing instead of stewing in sullen silence. Then, after a few years of regular performances, an exciting opportunity came his way. "They did a thing where Bill Bellamy would go from town to town and try to find comedians, and it was going to be a segment on Last Comic Standing," he told The Comedy & Magic Club. "If he scouted you, you leap-frogged the audition process." Naturally, this wasn't something Dye wanted to miss out on.

Fortunately for Dye, he had become adept enough at working the room that Bellamy was impressed by what he saw. "I didn't even audition for the show," he continued. "He just came and saw me, and said, 'You're going to be on Last Comic Standing.'"

Seemingly overnight, Dye went from a relative unknown to a regular on primetime NBC.

Although Kristin Cavallari's new boyfriend Jeff Dye didn't win on his season of Last Comic Standing – Iliza Schlesinger did, showing how tough the competition was — he came in third place, which is pretty impressive (via Laugh Spin). After the series concluded, all kinds of door opened up for Dye, including a holding deal and comedy specials. Naturally, it was time for Dye to make the inevitable move to Los Angeles.

Dye also started hosting television shows, something he's known for as much as he is known for being a comic. One of his first gigs was hosting the Ashton Kutcher-created comedy show Numbnuts on MTV, which he described as "Jackass meets Fear Factor." After that, Dye hosted Money from Strangers, and he appeared on a variety of shows, including Girl Code, Today, Lip Synch Battle, American Ninja Warrior, The Tonight Show Starring Jimmy Fallon, and The Masked Singer (via IMDb). That's a pretty impressive roster in and of itself, and Dye doesn't seem to be slowing down anytime soon.

In 2016, Kristin Cavallari's boyfriend Jeff Dye landed perhaps the best job of his career to date: he was cast in the reality TV series Better Late Than Never. "It's a dream job," he revealed to Moontower Comedy News. "I'm flying first class [to] all these beautiful places, and getting to do all these first-class things with four guys that I really like." Oh, and those guys happen to be total legends: Olympic gold medalist George Foreman, actors Henry Winkler and William Shatner, and former NFL quarterback Terry Bradshaw.

During the first season, Dye accompanied the four icons as they toured Asia, and he joined them in Europe and Morocco in the second season. And as Dye told it, they were received warmly everywhere they went. "Since the show, everybody wants us to come to their hotel," he continued. "Everybody wants [us] to come their restaurant." He added that people were eager to meet his four fellow companions, and it's not hard to see why.

While Kristin Cavallari's new boyfriend Jeff Dye has enjoyed success in comedy and television, he's also been personally touched by terrible tragedy. In 2015, Dye's sister Janice Lee Dye was killed in a car accident, according to the Albany Democrat-Herald. As Dye told it, his sister was distracted by a phone call when her car was hit by another driver, who was texting at the time. "It's definitely the worst thing that's ever happened to me because one, she was like a mom figure, and we were really, really close," he recalled in an interview with The Honeydew. We're so sorry for your loss, Jeff.

Dye also called his sister one of the most thoughtful and generous people that he'd ever known, someone who would give you the shirt off of her back. So it's completely understandable that he quite literally threw up in the street when he got the terrible news. "It was really, really scary," he continued. And while Dye tried to soldier on in the immediate aftermath, he was very much impacted by his sister's untimely passing.

Part of being a stand-up comedian, no matter how big and famous you become, is going on tour to different cities. That's why Kristin Cavallari's new boyfriend has done what he can to make those long stretches on the road as bearable as possible. "Over the years, I've made friends in each town, whether it be comedians that live there, or friends that have moved away, or friends that I have made in the city by meeting at a bar or through another mutual friend," Jeff Dye explained to The Comedy & Magic Club. That certainly makes being in a new place every day a little easier to handle.

That said, Dye still has issues to contend with when it's time for him to hit the road. "It does get pretty lonely never being with the same people, or having real solid friends with me," he continued. Perhaps in the future he can bring someone along... maybe even Cavallari?

Kristin Cavallari's new boyfriend Jeff Dye has certainly had the chance to travel the world, thanks to his career as a comedian and his work on the show Better Late Than Never. But of all of the exotic countries he's been to, there's one place Dye would go back to in a heartbeat. "If I could pick one to go back to, I'd pick Spain right off the top of the bat because it's an easy place to love," he explained in a chat with Deepest Dream. "I can't imagine anyone going there and not enjoying it."

What exactly is it about the country that Dye loves so much? "Spain is beautiful people, beautiful weather, beautiful places, beautiful history," he continued. "Every night of the week there's something going on." If that doesn't make you want to pack your bags and jump on a plane now, what does?

Dye added that he's also extremely fond of Thailand as well, a place he said he loves.