Jennifer Aniston has spent most of her adult life in the spotlight, with all its glare. At 53, she opens up about her path to leaving regrets and some deeply personal pain behind.
BY: Danielle Pergament PHOTOGRAPHED BY: Zoey Grossman
If we’re being literal, the hills above western Los Angeles are actually the only place where Jennifer Aniston is the girl next door. That’s what people called her for a long time. The girl next door, which is a ’90s euphemism that means she’s unintimidating, approachable. But here, along avenues of impermeable iron gates, among houses hidden behind hedges grown to make sure you know your place, the vibe is pretty intimidating. To live here, one assumes, you have to have achieved a certain kind of Olympian status, like having been among the most beloved figures in American pop culture for 30 years.
This is what I’m thinking when the gates to her house swing open and I enter onto a pea stone car park. Pruned trees, gurgling fountains, 500-foot-tall front doors. Then suddenly, there’s a lot of barking and Aniston’s familiar voice, somewhere inside, reprimanding her dogs. When she opens the door — ripped jeans, tank top, barefoot — Aniston looks like she could be the owner’s out-of-town friend crashing here for a few days.
Chanel spring 1996 micro bikini top provided by El Cycèr Vintage, Gucci spring 1997 logo G-string provided by El Cycèr Vintage. Saint Laurent skirt. Bulgari bracelet. To create a similar makeup look: Stylo Yeux Waterproof in Noir Intense, Les 4 Ombres in Blurry Grey, Joues Contraste in Rose Ruban, and Rouge Coco Gloss in Rose Pulpe by Chanel. Photographed by Zoey Grossman. Fashion stylist: Shibon Kennedy. Hair: Chris McMillan. Makeup: Gucci Westman. Manicure: Kim Truong and Diem Truong. Set design: Jeremy Reimnitz/Spencer Vrooman Studio. Production: Viewfinders.
She welcomes me into the house, which looks like a comfortable art gallery and smells like a box of new shoes transported in a Louis Vuitton steamer trunk full of gardenias. “Excuse my frazzledness,” she says, seeming pretty unfrazzled, as we walk into her kitchen. “I just had a whole thing happen at work.” She’s in the middle of filming the third season of The Morning Show. “I just [found out I] have a few pages to learn of a huge interview scene.”
“Our interview can be a dry run,” I propose.
“Yes, this will be my dry — exactly. That’s exactly right.” Aniston at her most Aniston. It’s that thing she does. She murmur repeats — part bumbling professor, part conspiratorial best friend.
Immediately, she’s welcoming: “Can I make you a shake? I’m having a shake.” I am not about to refuse a homemade shake from Jennifer Aniston. Sure. Great.
“I want to introduce you to my dogs.” She opens the door to where they’ve been relegated. “Clyde is amazing, but Chesterfield gets barky. You have to ignore him. Even if he licks your hand and you’re like, ‘Oh, there’s my in,’ he will jump and it seems scary.” I do as I’m told: aloof and indifferent. I could be a French waiter.
“Okay, I’m making us a shake. Here we go.” I lean against her kitchen island and watch as Aniston begins to assemble the ingredients. Back and forth to the refrigerator, in and out of cabinets, collecting little containers of powders and a thing of nuts and then ground-up some- things and there’s a banana and then shavings of something elses. Am I okay with chocolate-flavored things? “Yep, but I’m a vegetarian so just no bacon, please.”
“Ha! I’m not going to put the bacon in! I’ll leave out the bacon. I’ll leave out the bacon.” Murmur, repeat, perfect timing.“Let me blend this. Hold on.” She blends. Chesterfield — a big white husky? shepherd? lab mix? — starts barking. She pours two tall glasses of smoothie. “Whoa, I hope you like sweet things,” she says. “Cheers.”
Gucci spring 1997 logo G-string provided by El Cycèr Vintage. Saint Laurent skirt.
We move to the living room — and step into two sides of Jennifer Aniston. There’s a wall of artwork and floor-to-ceiling windows. But there are also dog beds, a giant sofa with a slipcover, and a really casual vibe. She’s not a coaster person. Aniston sits on the floor and Chesterfield jumps on the couch next to me.
Earlier I was texting a journalist friend of mine. I told him I was interviewing Aniston and I asked him to give me smart things to say. “One thought is this,” he texted. “No one’s ever going to be famous the way she is. That kind of mass-fame phenomenon burning so bright for so long, it’s just not achievable today. She’s like a silent-film star among a generation of TikTok dipshits.”
I read her the text. “Whoa. Oh, that just gave me chills,” she says. “I’m a little choked up. I feel like it’s dying. There are no more movie stars. There’s no more glamour. Even the Oscar parties used to be so fun….”
There’s something that’s distracting me. Yes, I do have the feeling that whenever Jennifer Aniston fades into posterity (something that doesn’t seem imminent; she has two new movies coming out, and the third season of The Morning Show), the station of movie star will be diminished. But it’s not that. It’s her hair. Her hair is the second most famous thing in this house. You could say her hair was the second most famous thing on Friends. I can see the nuances, the parts of each strand that change to gold as she moves her head. It’s a little unsettling. Like seeing your own reflection in Tom Cruise’s aviators.
Isa Boulder bra top. Balmain pants. Grace Lee ring. Christian Dior spring 2003 logo embellished belt provided by El Cycèr Vintage. To create a similar makeup look: 5 Couleurs Couture in 1947 Miss Dior, Rouge Blush in 219 Rose Montaigne, and Dior Addict Lip Glow Oil in 001 Pink by Dior.
About a year ago, Aniston launched a hair-care line, LolaVie, with a simple and ambitious mission: “Create a product that is good for the environment, good for our hair, take out all the crappy chemicals, and have it perform,” says Aniston.
Then she says, “I hate social media.” This is unexpected. What do you mean? “I’m not good at it.” This seems…counterintuitive. As you may be aware, about three years ago, Aniston joined Instagram. She opened an account, posted a photo of the cast of Friends, and in the following hours, the platform rushed to accommodate so many thousands of Jennifer Aniston followers that it crashed. Is that what she means by not being good at it? Like, is it hard because you’re too popular? Like in a job interview when they ask you your biggest weakness and you say I guess I work too hard sometimes?
“It’s torture for me. The reason I went on Instagram was to launch this line,” she explains. “Then the pandemic hit and we didn’t launch. So I was just stuck with being on Instagram. It doesn’t come naturally.”
I ask her about this. How, to people like us, who came of age before InstaChat and SnapTube and FaceTik, social media can seem unnecessarily punitive, like checking in with the meanest girl from high school every 10 minutes to confirm you’re still a loser.
“I’m really happy that we got to experience growing up, being a teenager, being in our 20s without this social media aspect,” she says. “Look, the internet, great intentions, right? Connect people socially, social networking. It goes back to how young girls feel about themselves, compare and despair.
“I feel the best in who I am today, better than I ever did in my 20s or 30s even, or my mid-40s. We needed to stop saying bad shit to ourselves,” says Aniston, scolding her future self: “You’re going to be 65 one day and think, I looked fucking great at 53.” Something in her tone makes me think that this isn’t a typical “I’m proud of my wrinkles and gray hair” platitude. This goes deeper.
Isa Boulder bra top. Balmain pants. Christian Dior spring 2003 logo embellished belt provided by El Cycèr Vintage. Grace Lee ring.
“I would say my late 30s, 40s, I’d gone through really hard shit, and if it wasn’t for going through that, I would’ve never become who I was meant to be,” she says. “That’s why I have such gratitude for all those shitty things. Otherwise, I would’ve been stuck being this person that was so fearful, so nervous, so unsure of who they were.” She finishes her smoothie and reaches out to Chesterfield. “And now, I don’t fucking care.”
Maybe I look confused. She explains.
“I was trying to get pregnant. It was a challenging road for me, the baby-making road,” says Aniston, of a period several years ago.
On the scale of dumb things to say, this is the moment when I really hit it out of the park. “I had no idea.”
“Yeah, nobody does,” she replies graciously. “All the years and years and years of speculation… It was really hard. I was going through IVF, drinking Chinese teas, you name it. I was throwing everything at it. I would’ve given anything if someone had said to me, ‘Freeze your eggs. Do yourself a favor.’ You just don’t think it. So here I am today. The ship has sailed.”
We sit quietly for a minute, maybe sad for all the ships that have ever sailed. I almost want to apologize to Aniston for being a journalist. This doesn’t feel like any of my business.
“I have zero regrets,” she says. “I actually feel a little relief now because there is no more, ‘Can I? Maybe. Maybe. Maybe.’ I don’t have to think about that anymore.”
Back then — and for years — there were headlines swirling through pop culture that Aniston wouldn’t have kids. That she wasn’t interested or she just wanted to be a star or whatever idea was selling that week.
Adding to the personal pain of what she went through was the “narrative that I was just selfish,” she says. “I just cared about my career. And God forbid a woman is successful and doesn’t have a child. And the reason my husband left me, why we broke up and ended our marriage, was because I wouldn’t give him a kid. It was absolute lies. I don’t have anything to hide at this point.”
Aisling Camps dress. To create a similar makeup look: Ombres G Eyeshadow Quad in Majestic Rose, Tender Blush in Pink Me Up, and KissKiss Shine Bloom in Petal Blush by Guerlain.
I have flashes of every magazine rack, every airport newsstand. Those “Jen Has a Baby Bump!” or equivalent headlines were everywhere (including Allure). We all felt entitled to the cellular happenings inside her uterus. We consumed those headlines, then dropped them in the trash and got back to our lives. But she couldn’t.
“I got so frustrated. Hence that op-ed I wrote [for The Huffington Post in 2016, slamming the media for its obsession with her being pregnant and its treatment of women, generally]. I was like, ‘I’ve just got to write this because it’s so maddening and I’m not superhuman to the point where I can’t let it penetrate and hurt.’”
Chesterfield is back on the couch, trying to curl up on my leg.
“I think my mom’s divorce really screwed her up,” Aniston says when I ask her about growing up. “Back in that generation it wasn’t like, ‘Go to therapy, talk to somebody. Why don’t you start microdosing?’ You’re going through life and picking up your child with tears on your face and you don’t have any help.”
Chesterfield nudges deeper onto my lap. Aniston pulls him off. “Come here, baby,” she says. “I know you want to, but you just can’t lick people.” It’s one thing to be a dog person, but Aniston is next level.
“I forgave my mom,” she continues, getting back to her human family. “I forgave my father. I’ve forgiven my family.” (Aniston was estranged from her mother for years.)
Who among us hasn’t tried — successfully or not — to forgive our family? You in the back, put your hand down. You’re lying to yourself. Families are things to be forgiven.
“It’s important,” she says. “It’s toxic to have that resentment, that anger. I learned that by watching my mom never let go of it. I remember saying, ‘Thank you for showing me what never to be.’ So that’s what I mean about taking the darker things that happen in our lives, the not-so-happy moments, and trying to find places to honor them because of what they have given to us.”
Calle Del Mar bandeau and skirt. Jenny Bird earring. MAM ring. Tabayer ring. To create a similar makeup look: Longwear Crème Eye Pencil in Noir, Tinted Moisturizer Blush in Southbound, and Hydrating Lip Balm by Laura Mercier.
One of the things her parents’ divorce gave her was motivation to leave. “My house was not a fun house to live in,” she says, about her family’s apartment in New York City. “I was thrilled to get out.”
After graduating from LaGuardia High School of Music Art and Performing Arts in New York City, Aniston worked as a waitress at Jackson Hole diner on the Upper West Side, and at an ice cream place in Lincoln Center. (“I’d make a shake and if there was leftover…? I finished it. Why waste this? I was rounder then,” she says, arching her eyebrow.) Eventually, “I moved to California.” She arrived in Los Angeles “the summer of 1989, which was yesterday,” she says. “I walked into a party in Laurel Canyon. This girl says, ‘Come with us. We’re doing a circle.’ I was like, ‘What’s a circle?’ It was all women and they saged you before you went in. Then a talking stick, I’m sure with feathers on it. The women call in the four directions, and I’m like, ‘What the fuck is going on? Am I in a cult?’ Hours later, woman after woman, just speaking, sharing thoughts and fears, worries. How incredible women are for each other. That’s how I got into that world, which I guess would be called Woo Woo. It was very Woo Woo.”
The women of the Woo Woo circle remain her closest friends. She met the woman who would become her producing partner that night. All around Aniston’s house are framed photos of these women — hiking, traveling, smiling, sharing their lives, this close-knit coven of old friends. Students of Friends (and whatever you think of them, they are legion — just witness the cultural juggernaut that was the Friends reunion last year) will know that the show’s premise was about that time in life when friends are family. Aniston is a case of life imitating art.
“I remember in high school doing a Chekhov play,” she says. “It wasn’t funny, and I was making it funny. And my teacher said, ‘Why don’t you just be funny because you have it in you?’ And I was like, ‘How dare you? I’m a dramatic actress!’ Turns out, it was the thing that saved my life, comedy. It was a salve to make people laugh.”
“There are people who say that watching Friends has saved them during cancer diagnosis, or so many people with just so much gratitude for a little show,” she says, her eyes glassy with tears. “We really loved each other and we took care of each other. I don’t know why it still resonates; there are no iPhones. It’s just people talking to each other. Nobody talks to each other anymore.
Well, we’ve come this far. “Would you ever get married again?”
“Never say never, but I don’t have any interest,” she says. “I’d love a relationship. Who knows? There are moments I want to just crawl up in a ball and say, ‘I need support.’ It would be wonderful to come home and fall into somebody’s arms and say, ‘That was a tough day.’”
Smoothies long gone, Aniston gives me a tour of the house. Imagine soaring views and spiritual shrines tucked into corners. We walk into the dining room with its majestic table, heavy art books, charcoal walls. A few paint swatches are affixed to the wall. All in identical shades of charcoal. I don’t get it.
“You can’t see the difference?” she says. You’d think I just told her how much I love the emperor’s splendid new clothing. “Really? You can’t see how blue this one is?” This is paint swatch gaslighting. Paintswatching.
“I would love to be an interior designer. I love walking into a house that’s being torn apart and finding ways to put it back together,” she tells me, escorting us into her own personal metaphor.
“I feel like I’m coming through a period that was challenging and coming back into the light,” she says. “I have had to do personal work that was long overdue, parts of me that hadn’t healed from the time I was a little kid. I’m a very independent person. Intimacy has always been a little here,” she extends her hand an arm’s length in front of her. “I’ve realized you will always be working on stuff. I am a constant work in progress. Thank God. How uninteresting would life be if we all achieved enlightenment and that was it?”
