Kristin Cavallari Hopes She’s Not Famous Forever

Kristin Cavallari is looking down on me. It’s not her fault, exactly; that’s just the way her computer is set up. The reality-TV veteran is perched on a high chair in the center of her spacious bathroom in the tony Nashville suburb of Franklin, Tennessee, as two attendants do her makeup and hair. I’m at my desk in Los Angeles, background blurred.

Current seating arrangements notwithstanding, Cavallari insists that she has no interest in being placed on a pedestal. Though the 37-year-old represents a kind of physical ideal — lean, blond, petite, perky — she doesn’t claim to be perfect, just real. “I think people can tell there's an authenticity with me,” she says. “I just am doing what I'm doing.”

Her podcast is called Let’s Be Honest, and her Instagram loudly advertises the fact that she doesn’t apologize. No really, she doesn’t. Whether it’s about vaccinations (albeit 10 years ago) or Trump’s “locker room talk” (albeit she was just musing on the cultural context of the Access Hollywood tape) or casual sex (albeit, uh, why were people mad about this?), well, she said what she said. Whether it’s how she wants to be seen, or who she really, truly is — or maybe a bit of both — being unapologetic has become Cavallari’s brand.

But she and I aren't chatting today to unpack the depth of her authenticity; we're just here to talk. We make our way politely through the requisite topics, what she’s up to personally (moving to a different house 10 minutes away) and professionally (launching a fragrance, Hard Feelings, and developing new skin care products to be sold alongside the trendy minimalist home, jewelry, and apparel offerings of her brand Uncommon James). It’s just girl talk here. And, apologies to the Bechdel test, there is no girl talk like boy talk. So, I ask if we can talk about her relationship with 24-year-old TikToker Mark Estes.

She responds to me coolly: “What do you want to say?”

Cavallari was 17 when she was introduced to the world in the opening voice-over of Laguna Beach: “That? That would be Kristin, another junior. Wherever Kristin went, drama followed. She thinks she’s hot. OK, I guess she is, but she can’t stand me,” says likable, anodyne lead Lauren Conrad. At the core of the half-hour reality show is a classic teen love triangle: Sweet and innocent Conrad believes that her longtime friend Stephen Colletti is her soulmate, but Colletti has chosen to date Cavallari instead, making Cavallari the default villain. To be clear, Cavallari didn’t cheat on anyone or steal a boyfriend from another girl; she just dated a boy, without apologizing. This — and the fact that she appeared to fit the image of the Rich B*tch most of us would like to see knocked down a peg — made her Bad.

I didn’t watch the reality show when it aired from 2004 to 2006, but I remember how its leads were painted. The star was Lauren Conrad: the sweetheart in a headband, the girls’ girl, the best friend. Kristin Cavallari was positioned as her foil: too loud, too confident, too rebellious.

When she returned to reality TV in 2009, as an adult on The Hills, Cavallari embraced the role she’d been cast to play. Spencer Pratt called her a “real-deal female player,” and Cavallari lived up to the moniker, picking fights and proudly declaring herself the kind of girl you don’t want to mess with. Honestly, I still don’t. Twenty years after Laguna Beach premiered, the middle-schooler in me remains a little intimidated.

Was it an act? Not exactly. But Cavallari knew how to make good TV, and she learned how to play the media’s game. “She knows how to not over-expose herself to the point where people become tired of her, and she is incredible with setting boundaries for herself professionally,” says Justin Anderson, her frequent podcast guest, close friend, and celebrity hair guru.

In real life, a lot’s changed for Cavallari. No longer a SoCal girl trying to make it as an actor , Cavallari hasn’t even lived in California since 2013. That year, she married NFL quarterback Jay Cutler and moved to Chicago for his career. After he retired, the pair relocated to Tennessee to raise their three kids and for Cavallari to start her lifestyle brand, Uncommon James — a chapter she shared in the E! reality show Very Cavallari (2018-2020). But as the show wrapped and the world (temporarily) came to an end in early 2020, so did the marriage, and the couple announced their divorce in April 2020.

A fresh start was what the goal-driven Capricorn needed. “[The divorce] was when I let go of a lot of control, and I let life unfold before me instead of trying to plan everything and control everything. I’m way happier and I’m way more at peace in my life, so it’s working for me,” she says.

Her friends have noticed. “She’s going to roll her eyes at me for saying this,” says Anderson, “but I think she’s more vulnerable with her feelings now more than ever before. Just in the past four years, I’ve watched Kristin finally feel like it’s OK to deep dive in conversation about her feelings and open up about things in her past that maybe she’s always felt like she needed to put on a brave face about.”

Now, Cavallari believes she’s also physically in “the best shape” of her life, and it’s all thanks to carbs (if only 2004 could see us now!). “I’m eating the most carbs I ever have,” she says. “There was a period of my life where I would not go near a carb. I was even afraid of carrots for a while because I was doing keto coupled with intermittent fasting, and I actually think it messed up my metabolism, and it took me a year to stabilize. Now this freedom with food has been really nice.”

Complex carbs, simple priorities. Maybe leaving Hollywood gave her clarity on what really matters, or maybe she’s too busy for the superficial stuff. “My life is centered around my kids. I don’t have any help with my kids. I don’t even have an assistant right now, and so I just don’t have time for anything else,” she says. “All I want to do is make the money from my podcast and Uncommon James and do what I need to do for those.”

Which is good, because people are mad at her again. For dating a boy, again. And again, no one cheated; again, no one lied. Two single people found that they clicked. But if the 2000s were tripped up on a teen Madonna-whore complex, the 2020s are fixated on age-gap shaming. Estes is a TikTok Zoomer, Cavallari an MTV millennial. If you’re wearing pearls, now’s the time to clutch.

My life doesn’t affect you in the slightest. If that’s triggering for someone, they need to take a look in the mirror and figure out why.

Cavallari’s not unaware of the optics; she just doesn’t give them much weight. “I understand what it looks like from the outside world of, like, yeah, I’m dating a 24-year-old, but no one in my life has been like, ‘This is weird.’ Everyone’s like, ‘I get it. It makes sense.’” When she met Estes several months back, it was the first time as a fully formed adult that she’d been single, and she was pleasantly surprised to discover that there was no pressure on the relationship. Or no pressure coming from her end, at least. “I own my own house. I have kids. I don’t need a man for anything other than just pure happiness,” she says. And though he may be young, Cavallari certainly has the wisdom and experience to spot a good one. “Emotionally, he’s able to step up to the plate, and he’s shown up for me more than anyone else I’ve ever dated.” (And he gave her his shoes when her feet hurt! Plenty of men twice his age probably wouldn’t do that.)

It helps that Cavallari’s skin is thick enough for the both of them. “I’ve had 20 years of people b*tching about something I’m doing. I feel like my whole career has led me to this moment,” she says. “This is the first time in my life I truly have not given a sh*t what anybody thinks. I think if people are upset about it, that has nothing to do with me. You don’t know me. My life doesn’t affect you in the slightest. If that’s triggering for someone, they need to take a look in the mirror and figure out why.”

Still, Cavallari is human, and even after two decades in the public eye, it hurts her to be misquoted or taken out of context. “Things get misconstrued, and that drives me crazy. Like that’s not what I f*cking said! I shouldn’t probably say this, but even my own podcast company, they just posted something last week, and I had to comment: ‘That’s not what I was saying.’”

Most viewers of reality shows these days know that what they are watching is not, you know, “real.” Twenty-two years in, the Bachelor franchise, for example, is notorious for “franken-biting” (the practice of taking sentence fragments and putting them together to make it sound like someone said something they didn’t). But for those contestants, that’s what they knowingly signed up for. Cavallari, on the other hand, was a teenager at the dawn of the genre.

“I think I walked away from Laguna Beach thinking that I was the only one MTV messed with and I got the sh*tty end of the deal, and I took everything so personally,” she says. But in hindsight, she realizes, “they f*cked with everybody the same way they f*cked with me. ... We were very young to have our lives manipulated like that. I’m not complaining about it. I’m so thankful for the show. I think it can be both things — I can feel like we were taken advantage of, and I can also be thankful for it.”

She goes on: “At that age, 17, 18, no one really knows who they are, but it definitely made me be like, ‘I am not that girl on TV, but if there’s even a slight part of me that is, I know that I don’t want to be that.’ So maybe it actually was a blessing in disguise and made me be a nicer person in general.”

I’m so thankful for the show. I think it can be both things — I can feel like we were taken advantage of, and I can also be thankful for it.

Watching Laguna Beach now, I’m struck by how openly misogynistic it is. Stephen Colletti, our boy hero, gets drunk and calls Kristin a slut to her face. In a world where Taylor Swift’s “Better Than Revenge” no longer chastises the “actress” on the “mattress,” Cavallari might merit an apology from the powers that be at MTV who allowed a teenager to be the face of romantic jealousy. As we as a culture try to atone for the reflexive sexism of the 2000s, Cavallari could “reclaim the narrative,” make herself the defiant survivor of mistreatment a la Monica Lewinsky, Janet Jackson, and Jessica Simpson. She could also join the “reality reckoning” — calls for a union for reality TV stars, Housewives slapping Andy Cohen with lawsuits — but when I bring that up, Cavallari insists she hasn’t heard anything about it, nor is she especially intrigued. Anyways, she and Stephen did the re-watch podcast thing a few years ago, and she’s made peace with her past. Her reckoning is all reckoned out, and she doesn’t need or want your compassionate re-evaluation. “Everything has worked out the way it’s supposed to, and it’s gotten me where I am today,” she says. “So no, I wouldn’t change a thing.”

What’s more: As her peers vie for longevity in the biz, Cavallari hopes she’s on the way out. “My celebrity could go away tomorrow and I would be really happy. … I want to work for two or three more years and literally be done and then open up a coffee shop in a little beach town just for fun.” Once her kids graduate high school, “I’m not going to be in Hollywood. I’ll be done. I have a set amount of money in my mind, and then I’m done working. I just want to live a chill life. I’ve been grinding since I was 17, and I’m tired.”

I ask if she has anything else to add, but no, she’s good. She plugged her products, addressed the Estes of it all — and anyways, her hair and makeup are done, so it’s time for pictures. What do you want her to say?

Photographs by Caitlin McNaney

Hair: Marwa Bashir

Makeup: Katie Galliher

Onset Producer: Lisa Easterling

Talent Bookings: Special Projects

Video: Caitlin McNaney

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Photo Director: Alex Pollack

Editor in Chief: Charlotte Owen

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