Mindy Kaling on Her New Book, 'Why Not Me,' Out Today!

Photography by Olivia Malone
Styling by Shirley Kurata
Hair by Clariss Rubenstein
Makeup by Kelsey Deenihan
Production by Rosco Production

It’s late summer and Mindy Kaling—who is already deep into production on the fourth season of her sitcom The Mindy Project— is telling me about the fashion line she’s always dreamed of creating. “For a long time my fantasy was, I would have this clothing line called New Money. People wouldn’t be able to tell if it was real or a goof,” she says, with a laugh. “You know how Moschino sometimes has Looney Tunes as their runway motif? I would have, like, dollar signs.” She isn’t kidding. “I feel like, The only way to wear the thing I really, truly want to wear is to pretend I’m winking about it.”

Kaling, who once described her personal style as perfect for “a New Year’s Eve party sponsored by a men’s deodorant body spray,” underestimates herself. Today she’s wearing a sleeveless, pin-stripe dress from Creatures of Comfort and limited edition Adidas Superstars in metallic rose gold. We’re sitting down at a West Hollywood restaurant to talk about her new book, Why Not Me?, a very funny collection of essays about her life in Hollywood. But upon closer examination, Why Not Me? reveals itself to be something more. This is a sly, wise self-help book about being a woman in your 30s and figuring out what works for you; it’s like an undercover Lean In, but with jokes about Idris Elba and how wearing heavy, fake hair pieces sometimes gives you headaches. “Oh yeah,” Kaling says, ordering smoked trout and a side of biscuits, “that wig life.”

This is Kaling’s appeal: In a town obsessed with ass-kissing, she’s the perfect insider—that refreshingly honest best friend you wish you had, the one who puts her foot-in-her-mouth so often she can taste her heel, yet isn’t afraid to tell you about it. In one of the book’s juiciest stories, Kaling writes about that time she attended a baby shower for an “extremely famous pop singer"—only to get drunk, and offend her host by making a joke about crazy anti-vaxxers in Hollywood. (Kaling reveals: "Had I been one Champagne in, I could’ve backtracked so deftly you would think I was Michael Jackson moonwalking across the stage on his Bad world tour. Even two Champagnes and I could have charmed my way out of this by pretending I was being ironic the whole time. But not three.”)

Elsewhere in the book she writes about being invited to a State Dinner at the White House only to obsess about a crush of hers, texting him: “Elena Kagan looks hot as hell. Where are you?” Says Mindy today, “It’s usually when I think I’m being incisive and satirical and I end up saying something really offensive,” adding: “What I enjoyed writing—and what people respond to—is the part of Hollywood that deserves satire.”

But what’s most appealing about this collection (the follow up to her best-selling Is Everyone Hanging Out Without Me?) is the straight talk: on confidence, on body shaming, on marriage—as one-by-one her single friends fall. For someone who writes, stars in and produces a sitcom largely about modern dating, she’s refreshingly candid on the subject of conscious coupling. “I admire [a good marriage] when I see it. I think it’s a beautiful thing. In my 20s, and especially in my teens, I completely fetishized a wedding. But I think much less about marriage now. It’s less interesting to me.” Don’t get her started on Honey Funds: “I’m not an ATM!”

At 36, she’s thinking more seriously about having kids—"maybe imminently. I think I’ve decided that unlike everything else in my life, I’m going to be fast and loose about kids. I’m going to not actively plan, but if it happens, it would happen.“ She’s quick to clarify: "I’m not cavalier about who I would have a kid with. But the thing I ask every parent that I really admire, the one comment they all have is that they wish they had kids earlier.”

As if she’d had the time. Why Not Me? chronicles Kaling’s life from her days as a Dartmouth undergraduate —a girl desperate to fit in at a sorority only to walk away before initiation when she finds a better home with a comedy troupe—to a writer and supporting player on NBC’s The Office, and then the groundbreaking creator of The Mindy Project, where she employs something like 150 people. And there’s a calm about her, a calm that comes with success, but also an ease that comes with being in your 30s and finally having a real grasp of what makes you happy. There’s a must-read chapter in the book devoted to confidence—a topic she’s often asked about—and the secret turns out to be brutally obvious: Confidence comes from hard work, she writes. Yes, Kaling may self-identify as “shallow,” and yes she writes about sometimes wishing she were skinnier, but she states plainly: “Don’t wish for it with all your heart.”

Today, the girl who starts every Monday morning with an Egg McMuffin and a side of hashbrowns, smiles and laughs: “Like everyone else, I like get rich quick schemes and get thin quick schemes. When people talk about the way I look, it obviously bothers me. But the way it bothers other women that I know is just so astonishing to me. They’ve always managed to find me clothes at photo shoots. They’re never like, ‘We can’t dress this creature!’”

Kaling—who used to wash her bras in a salad spinner and once thought good style meant wearing a cardigan with a belt over it as a uniform—is evolving, and so is her style. She hasn’t given up on chain stores, though she’s discovered the importance of having a good tailor on-call. She recently wore nautical stripes from Old Navy to a summer wedding, but had the faux copper buttons replaced with something heavier. “It’s an old trick,” she says, adding: “I had tweed separates from Reiss. I replaced the hardware on it and people thought it was a Chanel skirt suit—which I could never afford. And I do well! I don’t know who can afford Chanel.” She has something like 100 pairs of shoes in her closet, but admits: “At a certain point, there’s only one way to dress as a comedy writer. You end up dressing like a hot L.A. guy: boyfriend jeans, Stan Smiths, and a grey t-shirt.”

Though she’s a minted Hollywood star, it seems she might be happiest in a writer’s room. She laughs the loudest when talking about an upcoming joke on The Mindy Project which, after being canceled by Fox, moves to Hulu this fall—with a hefty 26-episode order. When the show returns this month, her alter ego, Ob/Gyn Mindy Lahiri, is pregnant and about to give birth. “She wants to basically be knocked out two days before and woken up three days later—in full hair and make-up. I’m touring a high-end birthing suite. In the IV bag there’s spa water infused with lemon and cucumbers. It’s like, This is where Tina Fey gave birth and where she workshopped a lot of her Golden Globes material. Mindy loves it.”

While being tossed from the Fox schedule no doubt stung, Kaling suggests it might be a blessing. And she doesn’t hold back. “Being on a network is extremely, extremely rewarding but extremely difficult,” she says. “It’s very much built on the next morning and waiting to see the ratings. When everyone you know watches it on a different platform than Nielsen—and not really understanding how to change that—that’s challenging.” In vintage Kaling fashion, she can’t help but compare the rocky television business to love. “The analogy is so incredibly direct to dating somebody. Now I feel like I’m with a boyfriend who is just really psyched about being with me. Which, for every human who has ever felt that feeling, is really nice.”

Much has been written about Kaling’s own dating life; she had an on-again/off-again thing with B.J. Novak (whom she met on The Office), and they sort of became the thinking man’s Bennifer; they’re like the favorite celebrity couple of people who camp out for tickets to the New Yorker festival. There’s even a Tumblr page dedicated to their very modern relationship. She and Novak recently sold a collection of essays they’ll write together, landing a reported $7.5 million advance for the book, though she says they’re still figuring out exactly what the book will look like. On working with an ex, she says: “I don’t know if I would have written this book with him five years ago. But no, it’s not weird at all. We fight all the time. I’m hoping that the creative process will be lively but good.”

Seriously, that’s it? She once described their relationship as “weird as hell.” In Why Not Me? she writes about taking Novak to see the Pulitzer Prize-winning play Doubt on Broadway, only to watch him fall asleep on Edward Albee’s shoulder for two hours. She strains to put it all in perspective. “I’m not comparing our fame or charisma, but I love Anjelica Huston’s memoir. I love reading her talk about Jack Nicholson. I hope when I’m Anjelica Huston’s age that B.J. would permit me to write about him in that way. She’s writing about him as though he’s dead. I just can’t believe he’s cool with this. She’s wonderfully complimentary about him and his talent and visiting him on the set of The Shining or whatever. And then pretty honest about the times he was kind of a dickhead.”

For the record, Kaling doesn’t have a lot of time for dating—"I date on Saturdays,“ she says—though she’s out there and having fun. "I think as you get older, you know more and more what you like. It makes dating harder and easier, in a way,” adding that she’s grown out of the “Broke Stand-up” type. “You know, Someone who has a lot of rants but not a lot of money. That’s somebody I’m not interested in dating again. I’m surprised, sometimes even a nice strong crush will sustain me for a long time. For whatever reason, that Oscar Isaac billboard—of him in that David Simon miniseries—he’s so handsome. Besides being a great actor, you think you might be one of the handful of people who has a crush on him. Even with that mustache on the billboard where he looks uncertain.”

There’s a long chapter in the book—a sort of Sliding Doors parody of what her life would be like if she’d become a Latin teacher at The Dalton School in Manhattan (a path she’d once imagined for herself before moving west). I wonder if she thinks about moving back to New York, where she spent her early 20s.

“I do,” she says, thinking, taking her time. “The show shoots in L.A. but I always think, after this, there’s nothing keeping me here. I’m doing fine here. I love my friends. But New York was wonderful when I had no money. It would be even better with some disposable income. I don’t know. I always fantasized about writing a movie there.”

For now, she has at least 22 more episodes to film. I wonder if she’s thought about what she might wear to the Oscars.

Kaling was the voice of Disgust in Pixar’s Inside Out, which earned more than $700 million worldwide this summer and feels like a lock for a Best Picture nomination. She wonders if the producers would have enough tickets to invite her, then says she might like to collaborate on her own Oscar gown. Suddenly it’s like Inside Out in here, and the emotions are ricocheting. If nothing else, I say, Disgust seems destined to become a Halloween costume this fall. She laughs: “That is a good Halloween costume. But I’m going as Justin Theroux. That’s what I want to be for Halloween. I’ll buy a leather jacket, leather pants, a low-cut v-neck. Awesome hair.”

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