I am meeting Mindy Kaling at the office. Only, in a mid-century building at the Los Angeles Center Studios in downtown LA, the vibe is more Sterling Cooper than Dunder Mifflin. (Mad Men actually used to shoot here, and large posters of that cast continue to watch over the lobby.) When I arrive a few minutes early for this interview on a recent Friday morning, Kaling is still on her way in, so an assistant guides me into Kaling’s office to wait. The workspace, one of several Kaling maintains, is a mini museum of her life and career. Behind her desk, cabinets are lined with artifacts: a collection of baseball hats from shows she’s worked on; her old Dartmouth mailbox, gifted to her by her alma mater; the words “Never Complain, Never Explain” embroidered on mustard fabric in a bedazzled frame (a gift from her close friend and ex B.J. Novak). There are also framed photos of her children — Katherine aka Kit is 8, Spencer is 5, and Anne is 2 — and a framed selfie of Kaling and Novak.

“It’s really fascinating to me that, personally, nothing really happened the way that I imagined it would,” she tells me a few minutes after she breezes into the room, petite and polished in a black Chanel cardigan, jeans, and chunky gold jewelry. Her hair is pulled back, her lips painted a glossy plum.

Her plan was simple: become a comedy writer, get married at 24, have her first baby at 27, complete her family by 32. Romance, or at least the version of love depicted in the movies, loomed large in her life from an early age, and still does in her office: Her desk is mostly bare save for a small collection of books, including rom-com touchstones like Bridget Jones’s Diary and the scripts for When Harry Met Sally… and Four Weddings and a Funeral (plus a pink notepad with “Mindy Kaling” scribbled in bubble letters and surrounded by stars). But Hollywood was 3,000 miles away from her childhood in the Boston area, so the girl born Vera Mindy Chokalingam — her parents gave her that middle name after the sitcom Mork & Mindy, infusing her with a direct line to pop culture from infancy — picked a goal that felt a little closer to home (and thus a little more achievable): writing for Saturday Night Live.

A teenage Kaling had laid out her personal timeline with such conviction that when she actually landed a job writing on The Office at 24 and moved to LA, it seemed only natural that the other pieces would fall into place. Instead, “literally none of that happened,” Kaling, 46, says. “All I wanted was a serious boyfriend and to follow this path that I’d set out for myself. I remember feeling like an overachiever at work and just wishing that my personal life matched my professional success — and it didn’t.”

An overachiever she was: Kaling forged ahead and spent the next decade and a half cultivating a career that included creating and starring in 117 episodes of her own comedy series (The Mindy Project) and becoming a tour de force across film and TV, both in front of and behind the camera: She acted in movies like Late Night, A Wrinkle in Time, and Ocean’s Eight, voiced Disgust in Inside Out, and segued into co-creating and writing TV shows including a Four Weddings and a Funeral miniseries, Champions, Never Have I Ever, The Sex Lives of College Girls, Running Point, and her latest show, Not Suitable for Work, which premieres June 2 on Hulu.

“It is crazy for someone like me, who only wrote about the pursuit of romance for so much of my life, to be very happy and content without a partner.”

To observe Kaling at the start of a day’s work is like watching a queen prepare to preside over her hive. Her current routine involves shuffling between the writers’ rooms of Not Suitable for Work Season 2 and Running Point Season 3, which convene down the hall from each other in this same building. She views Not Suitable for Work as the third part of a “trilogy” of shows very loosely based on her own coming-of-age experiences: Never Have I Ever showcased an Indian American high schooler and her family, The Sex Lives of College Girls followed a group of friends on a New England campus, and Not Suitable for Work highlights neighbors navigating their early 20s and fledgling careers in New York.

On NSFW, she’s sprinkled elements of her young adulthood across the lead characters: AJ (Ella Hunt) is an ambitious Bostonian with a chip on her shoulder, trying to get ahead in a male-dominated industry; Kel (Nicholas Duvernay) is an aspiring actor; Davis (Will Angus) just longs to find love; and Abby (Avantika) is a creative spirit dealing with more traditional parents. (Kaling’s own parents — an architect dad and an ob-gyn mom — immigrated to the U.S. shortly before she was born.) “Those time periods are just so juicy. When I was younger, I didn’t have the same compassion for 20-year-olds that I do now. I was like, They’re all my competitors,” she says between delicate bites of a veggie burrito that had been placed squarely in front of her chair in anticipation of her arrival. But now, she adds, “I have so much love and compassion — for both the younger version of myself and all of these characters.”

“Of course, it’s never a joy to be scrutinized, but also I truly understand it, as someone who consumes pop culture.”

Her own early 20s were full of 18-hour days spent “scraping by,” she says. “All I wanted to do was have health insurance, make money, and write on a hit show because I was so insecure and panicked about my career.” An off-Broadway play she cowrote and costarred in — Matt & Ben, about a pre-fame Matt Damon and Ben Affleck — got the attention of Greg Daniels, who was in the process of adapting The Office for an American audience and offered her a job. Over the next eight years, Kaling wrote on two dozen episodes while also embodying the drama-loving Kelly Kapoor on-screen.

It wasn’t until after she left The Office in 2012 and found success with The Mindy Project, on which she starred as an ob-gyn partly inspired by her mother, that she began to think beyond her own trajectory and consider the impact she could have on the industry. “I didn’t come into this career in 2004 as a scared 24-year-old thinking in a community-minded way,” she says. “That has completely changed in the past 20 years.”

In her 30s, Kaling focused on creating projects with her production company, Kaling International, and has repeatedly cast actresses of Indian descent in prominent roles, including Maitreyi Ramakrishnan, Megan Suri, Amrit Kaur, and Avantika. “I love seeing young women, particularly young Indian American women, and how different they are than I was at the same age, how confident they are, how unafraid they are to be activists, speak their mind, do their craft,” Kaling says.

After Avantika appeared in an episode of The Sex Lives of College Girls, Kaling reached out and invited the then-17-year-old actress to lunch. “She literally was like, ‘I just want to know what you like and what kind of movies you like to watch, and what you want to do in this industry,’” Avantika tells me.

Now Avantika has a starring role on Not Suitable for Work as an aspiring stylist. Kaling’s projects often feature “complicated, funny, charming, brown women that are all different, that are all beautiful, and all seem to be serving more purpose than one,” Avantika says. “That’s important for young girls to see. I don’t think just seeing themselves [on-screen] is, quite frankly, enough. We need to see our spirits represented. And I think Mindy does a really good job of doing that.”

Perhaps because Kaling once shared so much of her life in her books of highly personal essays (2011’s Is Everyone Hanging Out Without Me?, 2015’s Why Not Me?, and 2020’s Nothing Like I Imagined), many of her fans view her as a close friend — and feel entitled to know more about her life outside of work. But Kaling tells me that she has “very specific rules” about what she decides to share publicly. Her children’s faces, for instance, are off-limits.

She has also set boundaries around discussing her body. Kaling rose to fame as a self-described “normal-slash-chubby woman.” In “Chubby for Life,” one of the essays in her first book, she detailed her struggle with her weight as a child and teen, and her love of attempting fad diets.

“It’s one of the biggest mysteries in my life, this fervent knowledge that I knew I had to have kids that was not based on any real love of children.”

Kaling, of course, is no longer chubby for life. Over the past few years, she has lost a significant amount of weight, and any photo she posts of herself these days comes with an onslaught of comments assessing her body and speculating about how she got there. (Kaling has said she focuses on food moderation, running, hiking, and strength training.)

One of Kaling’s charms has always been her vocal enthusiasm for celebrity culture writ large, and she gets why some fans may feel frustrated. “It’s sometimes no fun when one of your favorite actors loses weight. You have an idea of what they were like when you grew attached to them, and it made them endear themselves to you,” she says. “Of course, it’s never a joy to be scrutinized, but also I truly understand it, as someone who consumes pop culture.”

Her decision to lose weight, she says, was motivated by concerns around her health and the realization that she needs to “live at least 20 more years” for her children. “Do I wake up every day being like, ‘I look amazing and I’m so gorgeous’? No, unsurprisingly, but I truly feel so healthy,” she continues, adding that she may write about her weight-loss journey in the future. For now, she holds the boundary at talking about her motivation. “When I was younger, I would want to lose weight because of vanity reasons. Now I want to lose weight or have lost weight because I want to stave off things like diabetes. I had it on both sides of my family, and trying to avoid those kinds of things will, I think, help longevity for me, and that’s my goal.”

Another boundary: her path to parenthood, particularly as it concerns the relationships in her life. While most of Kaling’s projects involve romantic storylines with an array of suitors, Kaling’s most prominent public relationship has been with Novak. The duo dated on and off from 2004 to 2007 while working on The Office, he’s the godfather of her three children, and the pair continue to refer to each other as “soup snakes” (an Office reference about soulmates). “He really is in our family, and I love talking about him because my kids adore him, and he’s such a huge part of our life. But I also know that it gives people a lot of ideas,” she says. “If I was just watching it from the outside, I would have the same questions and the same reactions.”

In an interview on Armchair Expert last year, Kaling said she wasn’t dating anyone and couldn’t remember the last time she’d even had a crush. That’s still the case, and she’s not “actively searching for that person,” she says now.

“I obviously have eyes and ears, and if there was someone that I had a crush on, of course I would react to that, but right now, there is not anyone out there,” she continues. “It is crazy for someone like me, who only wrote about the pursuit of romance for so much of my life, to be very happy and content without a partner.”

Though Kaling shared pregnancy photos and announced the births of her children on social media, to this day she has not revealed who their father is or the specifics around her road to motherhood. Perhaps, she says, she might talk about it publicly when they’re older. “The ramifications are so immediate for them that I just want to make sure that however I talk about it is in a way that really respects their privacy,” she says.

For Kaling, the decision to become a single mom “felt really crazy.” Although she always knew that she wanted to have children, she was never actually “a kid person.” “It’s one of the biggest mysteries in my life, this fervent knowledge that I knew I had to have kids that was not based on any real love of children,” she says. “B.J., for instance, he’s always been a kid person. He has a brother who’s 13 years younger than him, and he loved his little brother and just always has been a kid person. It’s such a deep mystery why I needed to do it.”

“As a single parent, I don’t want my children to be Hollywood orphans who just never see any parent while I shoot the show.”

In fact, Kaling says, the idea of having kids “really scared me.” But after Kaling’s mother died of pancreatic cancer in 2012, her desire to have children became “an insane certainty,” she says. “It was one of those things where it was not cerebral at all. It was just a decision that was completely moved by my soul.” At times, doing it alone has “been enormously challenging,” she says, “but I’m so lucky because I waited till I was older, and I have more resources. I have an incredible nanny. My dad and stepmom are a huge part of my kids’ lives. It’s been so much better than I ever thought it would be.”

When I spoke to Kate Hudson, who stars on Running Point as the owner of a fictional basketball team, she jumped to discuss Kaling in a parental context. “She’s such a good mom,” says Hudson, who also has three children. “It’s so impressive to me when women can have so much that they’re doing and be in so many places and still be able to prioritize, always, her kids. She does that in spades. She’s a great mom, but she always shows up for everything that she’s doing. She doesn’t miss a beat.”

On the work side, Kaling has been juggling multiple shows simultaneously since the pandemic era, even writing episodes on each of the shows she’s created and executive-produces. “Even if I’m splitting my time, I want to be able to be involved enough with the show that they could assign me an episode, and I would totally understand it,” she says.

Kaling’s Running Point co-creator and former The Mindy Project costar Ike Barinholtz has seen Kaling evolve in her approach to work over the past decade. “She’s really gone from someone who was, I would say, almost a workaholic type A to having a pretty good balance now,” he says. “We get to the writers’ room, and we always have 15 minutes of gossip and talking about shows we watched and showing funny clips of stuff online, but then we really lock in. And she’s able to, at four or five o’clock, be like, ‘OK, I’m going to make dinner for my kids.’ Watching her balance all this stuff — multiple shows and movies and kids and friendships — she never ceases to not impress me.”

When I was younger, I didn’t have the same compassion for 20-year-olds that I do now. I was like, They’re all my competitors. I didn’t come into this career thinking in a community-minded way.”

She’s eager to act on-screen again, something she’s put on the back burner for the past few years. “Sooner rather than later, I’d love to come back,” she says. “As a single parent, I don’t want my children to be Hollywood orphans who just never see any parent while I shoot the show. But, because of streaming, I could maybe do, like, eight or 10 episodes and have a shorter order than what we used to do on The Office or The Mindy Project.” Those shows maxed out at an exhausting 28 and 24 episodes per season, respectively.

One idea she’s intrigued by is creating and starring on a show about dating in LA in your 40s. “Whether you were never married or divorced or widowed, what does that look like?” she says. “That’s the kind of show that I would want to watch.” (Despite my request for a Kelly Kapoor spin-off series, Kaling is not sure a Kelly-centric show could work. “I wouldn’t say that I think she was the most three-dimensional character,” she says. “Kelly, in her mid-40s, I think she would have one of those TikToks where she was like a floating head, and she’d be criticizing red carpet photos from Scranton. Maybe divorced with a kid or two.”)

The Hollywood careers Kaling most admires are those of Jordan Peele and Greta Gerwig, creatives who steered their initial career paths — sketch comedy for Peele and acting for Gerwig — into writing and directing projects that retain what Kaling describes as a “spiritual link” to their earlier work. She’s particularly interested in writing and directing a horror or thriller film. “There’s a lot of overlap between horror and comedy.”

As we part ways, Kaling heads across the lobby to the Not Suitable for Work writers’ room to hear a pitch for a Season 2 episode before crisscrossing the lobby again later that afternoon to finish an outline for a Season 3 episode of Running Point.

The next morning, she planned to get up early, drop her kids off at various playdates and lessons, then go by herself to a 9:30 a.m. showing of The Devil Wears Prada 2. (Her ensuing Instagram story of one of Novak’s scenes seemed to confirm all went according to plan.) In its own way, it sounds like a dream life — even if it looks different from how she once pictured it.

“Professionally, I always wanted to write on Saturday Night Live and be a cast member on Saturday Night Live,” she says. “Personally, I wanted to be married. Neither of those things happened.”

But those things could still happen, I point out.

“That’s interesting,” she says, pausing in careful consideration. “Those things could happen, but I think I don’t necessarily need them anymore, maybe, which is a nice feeling.”

Top image credit: Khaite jacket; Ferragamo dress.

Photographer: Christian Soria

Stylist: Carolina Orrico

Writer: Ashley Spencer

Editor-in-Chief: Charlotte Owen

Editorial Director: Christina Amoroso

Creative Director: Karen Hibbert

Set Designer: Bette Adams

Hair: Becca Mader

Makeup: Eva Kim Lamy

Manicurist: Kimmie Kyees

Video: Andrew Daugherty, Kristina Grosspietsch

Photo Director: Jackie Ladner

Production: Danielle Smit, Kiara Brown, Aubree Lennon

Fashion Market Director: Jennifer Yee

Fashion: Stephanie Sanchez, Ashirah Curry, Noelia Rojas-West

Features Director: Nolan Feeney

Social Director: Charlie Mock

Talent Bookings: Special Projects