Mallory Ortberg's Internet

I'm about to ask Mallory Ortberg about the rise and fall of The Toast, the feminist website she co-founded, where her writing accounted for about half of the posts and has led multiple strangers to publicly propose to her. But before I do, Ortberg flips a question at me, instead: What did I already discuss with her Toast co-creator, and best friend, Nicole Cliffe?

Cliffe and I talked about persona versus personhood, I say. Who people are online versus who they actually are. You know, in real life.

Ortberg smiles and looks down at the table. It's November 2016, and we're sitting in downtown Oakland, California, where she has been stapling pamphlets together. She's wearing an outfit entirely composed of sweat material, sleeves pushed up to reveal forearms constellated with red freckles. The words PARK CITY, emblazoned on the sweatshirt that she just bought on a trip to visit Cliffe in Utah, crinkle together.

"What's your religious background again?" she asks me. "Only people who grew up religious say 'personhood.'"

Okay, she's right. And it is perhaps this kind of observation, this "I get where you're coming from," that connected readers most to Ortberg—and to Cliffe, the other contributors, and each other: The feeling that they were a little more seen, understood precisely because and not in spite of their particulars and peculiarities, linguistic or otherwise. They had lived their lives thinking they were the only one—alone in remembering Madeleine L'Engle's Bible fan fiction, or loving femslash fantasies featuring Gilmore Girls characters.

"And then across the mists of time we found each other," Ortberg says, speaking of the Toast community. "And I just think that's wonderful."

For three short years, The Toast became a nesting spot for regular readers. They flocked there daily to read posts like "Everyone Has Imposter Syndrome Except for You" and "Bible Verses Where 'The Messiah' Has Been Replaced With 'King Shit of Fuck Mountain,'" to comment not just about those posts but also about their lives, and to seek refuge in that rare online habitat: a place where people engage respectfully, in the best and worst of times, sickness, health—the whole bit. Whether they needed emotional support, a wake-up call, validation, money, or organs (really), the readers were there for each other.

So after Ortberg and Cliffe shuttered the site last July, many readers said to each other, "Till death do us part." On Slack channels, on Twitter, IRL, they have kept their community.

Ortberg did not exactly plan for this—beginning, middle, end, afterword. According to her sister, Laura Turner, she's not a planner at all. Yet her evolution set her up to do exactly this: create, using words, an online space where people laugh, connect, and grow. "The Toast gave voice to something that was always there in Mallory," Turner says, "and would have been there whether she prepared for it or not."

But what is the there there, that was always there in Mallory? To find out, and to learn how it translated to The Toast, I talked with Turner, Cliffe, and managing editor Nicole (Nikki) Chung; spent a church morning with the Ortberg parents; and communicated with around 40 Toast community members and contributors.

How did Ortberg come, personally and professionally, to co-create a site that not only wasn't full of trolls but also actively fostered goodwill among the users and readers? And what happens when you're essentially an internet star, with your own site-centric community, and then you move on—but they stay?

Ortberg stops stapling the pamphlets. It's nearly time to go record an episode of Slate's Dear Prudence podcast, which she hosts. But before we leave, she opens a laptop to check some edits on a piece she's writing for The New Yorker. It's a mashup of Gilmore Girls and Shirley Jackson's "The Lottery."

Gilmore Girls is coming back, she tells me, looking at her keyboard. She only watched the first three seasons of the original, though. That's her thing. "I love abandoning TV shows," she says. "I just don't have it in me to really commit. I feel like I got to enjoy that world for a good long time. And I love getting out."

Then she slips her sunglasses over her eyes before we leave the building, even though it is not really that bright out.

The philosophies of human interaction and humor that made The Toast a pleasant place began in Ortberg's home. She was raised by two religious parents: John Ortberg, senior pastor at the non-denominational Menlo Church, and Nancy Ortberg, CEO of Transforming the Bay with Christ. Given that, assuming is easy. They must have been ultra-controlling of their children's behavior. They probably aren't happy they have a queer daughter who has tweeted statements like, "Don't you ever try to autocorrect 'cunty' to 'county' again, you cunt phone."

But some of The Toast's, and Ortberg's, most salient characteristics came from her parents. "Irreverence was inculcated in our family," says Turner, her sister.

At dinner, John paid his kids a dollar for every good joke, and they wandered through riffing narratives together. "They were trying to make that a safe space to say what you're thinking," says Turner. It was the same, in other words, as The Toast, which was equal parts pastiche literary experiment, stand-up show, personal essay, debate podium, and hearts-covered sleeve.

Ortberg was funny even when she was a kid. But she learned through trial and error how to wield humor well. When she was younger, she found herself saying sorry, sorry, to friends she had harmed for a laugh. "How many times do I have to apologize to people before I think maybe I should think before I speak?" she recalls wondering. It's something she has tried to leave behind, in personal interaction and writing, ever since.

Her writing voice—punchy, pointed, precise, whip-smart—came at an early age, too. The credit for access to beautiful language, she says, goes to religion. It gave her great books, great thinkers, and also "a deeply compassionate way of looking at other people and thinking about personhood and humanity."

"You said 'personhood,'" I point out.

By the time Ortberg applied to college, she knew more about the self she was becoming and how it might diverge from the path she'd been following. "I saw a few things coming down the pike that I wanted to avoid, like dating women and maybe not so much believing in God," she says, although she's now back to being more open to spiritual scaffolding. So she did the logical thing and applied to Azusa Pacific University, a Christian college near Los Angeles, where she knew she would feel comfortable and safe.

"I had really hoped that I would just be the type of person who just dated girls in between boyfriends, so I wouldn't have to tell my family," she says. "And that just wasn't the amount of queer that I was."

When she did inform her parents that she was dating a girl, she almost wanted them to respond with fireworks, Roman candles aimed right at her. She wanted someone to be angry at. Instead, she says, "they were really loving and pretty open-minded."

Still, it was hard to talk about. But that taught Ortberg that conflict, done right, could bring people closer. And it taught her what "conflict done right" meant. No defense, no offense, just openness and gentleness. It's the same sensibility she and Cliffe would use when founding The Toast.

When Ortberg left college, she didn't see any other graduates like her, or anyone she wanted to be like. She had let herself flow into the life of least resistance. And she understood, now, that she could never let that happen again. "I did not pursue my best self," she says. "I did not look for challenges. And I'm really sad about that."

But Ortberg had graduated during the recession and was living unemployed in West Covina, California, eating In-N-Out and crying a lot. Roiling in that inner turmoil, she discovered The Awl—a site with an About page that says only "Be Less Stupid." Finding The Awl was like that episode of The Simpsons where Homer walks into a party and everyone is drawn like a New Yorker cartoon. Every writer, and every commenter, seemed like a brilliant genius. She aspired to be like them, one of them.

Soon, she moved back to her parents' house in the Bay Area, and The Awl launched the The Hairpin (About page: "Ladies first"). Ortberg began getting up early just to comment there, concocting the right admixture of intelligence, humor, and barb. Her avatar was a snapping turtle trying to eat a strawberry. It was a lot like Ortberg herself: funny, biting, likable, lightly shelled off.

Then she moved out, got a job at an academic publishing house, and became a regular commenter who began pitching stories first to The Awl and The Hairpin, then to Gawker and The Gloss. It was in The Hairpin comments section that Ortberg met Cliffe, who was then the books editor. Cliffe believes she wrote Ortberg first. "I like you. I really like you," Cliffe recalls saying. "I want to meet."

Ortberg remembers it differently.

"I was just like, 'We are going to be friends,' which is how a lot of my friendships start," she says. "I'll just inform someone we're going to be friends now. I've collected sufficient information. Friendship is going to happen now. Do you agree?"

Regardless of who went first, Cliffe bought Ortberg a plane ticket to visit her in Utah. They ran into each other's arms like their life was some over-soundtracked movie.

Soon, both felt the prick of desire to do their own thing, together. Ortberg had started weekend-shifting at Gawker, writing hourly stories. She'd learned to stop fretting too much over phrasing. "There was the sense that you were of course trying to do good work, but a piece gets published because it's 10 AM, not because it's great," she says. She made enough money with that gig and other freelance work to strike out on her own.

Around the same time, Cliffe had filled in as The Hairpin's head editor for a week. And she liked the feeling.

"We often talked about how great it would be to start a site together because we admired one another's work so much," says Ortberg. "And then we did it."

The Toast launched in July of 2013.

What The Toast was, exactly, no one—not even its creators—can say.

"We were really bad at elevator pitching it," says Cliffe. "It's always been just the set of things Mallory or I thought were funny or good."

People on the internet agreed about funniness and goodness. But they also seemed to respond to being let in to Cliffe and Ortberg's private world. It's a space, and a type of friendship, adults don't find often. It's a chemical kind of connection, where you can immediately be the person you've always been (but better) and grow safely into the self you have always wanted to be. It's the same sentiment Ortberg's parents fostered.

And it worked for The Toast, on which people alighted daily. "They showed up there every day, and it was like showing up to Central Perk on Friends," says Turner, "except it was on the internet and Chandler Bing wasn't there."

They stayed, to read social commentary captions on Western Art and personal essays about identity, to expound upon them in the comments, and to discuss their hearts' contents on the open threads. Ortberg carried over her Hairpin series "Texts From," in which she explored classic literary characters through text messages. That revival brought a publishing deal, and in 2014, Texts From Jane Eyre landed on the New York Times bestseller list.

But as funny and touching as Toast posts were, the comments could match them. And for some readers, the site's significance surged as much—or more—from the discussion. "Over time it became more about the community," says Toastie Kristen Hicks. "It was a comfort zone to hang out in whenever things in my life were bad and just a nice place to be when things were good."

The Toasties just belonged there. When Bendta Schroeder, for instance, finished a literature Ph.D. and was deciding whether or not to stay in academia, she worried leaving her field also meant leaving the bookish people she'd swarmed with. But The Toast gave her that community outside of academia—and likely contained far fewer guys mansplaining Foucault.

"On The Toast, because of the way the comments were moderated, people could unfold their reasoning in ways that were both sensitive and incisive," Schroeder says.

Cliffe and Ortberg both believe that the commentariat deserves most of the kudos for that. Sure, the two of them set up the conditions of the experiment, and deleted bombs before detonation. But the group followed their lead and guidelines of how to communicate in times of strife and conflict. "Not in the way where civility is the highest possible good," says Ortberg, "but generally attempting to talk like you might in person. Which is to say, 'I think that's a really bad idea. Here's what I think instead,' rather than, 'I hope you die a thousand times.'"

All of this funniness and goodness led other outlets to call The Toast, variously, "Mallory Ortberg's utopia of feminist humor" (Huffington Post), "one of the best sites on the internet" (Slate), "the site that was just for you. Yes, even you" (NPR), and "a singular presence online" ( Washington Post ).

It was too good to last forever.

Soon, The Toast brought on new staff. There was Marco the Tech Goth; Chung, who started as a part-time assistant editor and soon became the full-time managing editor; and Jaya Saxena, a staff writer. They launched The Butter, a vertical helmed by writer and professor Roxane Gay. They had a stable of stellar freelancers.

But the site's finances, while good for a publishing startup, weren't necessarily stable or sustainable. "It paid for itself and enabled us to pay everyone except Nicole," says Ortberg, "but we would not have been able to hire full-time replacements without asking them to work massive amounts of overtime."

That money situation was stressful because Cliffe, formerly of a hedge fund, had fronted money for the site, and had to bail it out in times of trouble. One day, when the tax guy forgot to tell Cliffe he'd made a payment, she had to run to the bank in penguin pajamas to move $20,000 into the site's account. She'd never drawn a salary, although everyone else had. She'd had a second kid.

Meanwhile, Ortberg had gotten a second book deal and a job, which she still holds, writing Slate's advice column, Dear Prudence.

"She was tired," says Cliffe. "Nikki was able to take a lot of stuff off my plate that made things easier for me, but there's no replacement for Mallory."

And while Ortberg wasn't yet burnt out, she saw the extinguishment coming. "It was getting to a point where it was not like, 'I'm going to go bonkers tomorrow and quit,'" she says, "but just a real sense of, 'we don't have another three years of this in us.'"

She and Cliffe talked through options. They could sell the site to a larger publisher, or pass it off to their employees. But they didn't want to watch The Toast become something it wasn't. And, in the words of both co-founders, they would have been handing employees "a millstone," rather than an opportunity.

Finally, they considered this: What if they just had a really fun three years, and then they stopped?

On the site's last day—July 1, 2016—one of its final posts came from Hillary Clinton.

"I know that today is the final day of The Toast, and I wanted to take a moment to reflect on what this space—and spaces like it—mean for women," Clinton began. She had always admired, she said, women "who take it upon themselves to create spaces where women can speak their minds freely. With this site, Mallory, Nicole, and Nikki did the same for so many women."

For Ortberg and Co., that's hard to top.

"I feel pretty strongly that that is the best job I'll ever have," Ortberg says, now. "I think that The Toast is always going to be a high-water mark."

But when The Toast left, the Toasties stuck around, and to each other. Eighteen areas, mostly in the US but a few abroad, have founded meet-up groups. There's a subreddit, a group on Fitbit, and one on Goodreads. And then there's #ToastieTwitter, or what member Erin Nelsen Parekh describes as "an instant circle of friendly faces on a fairly cutthroat platform."

Most lingerers, though, hang out on the Slack channels.

Chung, now managing editor at Catapult and author of an upcoming memoir about adoption, sometimes slips into Slack. She says she's impressed, but not surprised, by the depths of the community's commitment to each other. If anyone could self-organize, it would be the Toasties, right?

Ortberg, though, doesn't plan on checking in with lingerers on Slack. "They don't need me," she says. "Not, 'They don't need me' like 'I'm going to go die on a mountain.' Just the sense that they have this amazing thing that was kind of connected to the thing that I did but was very much their own."

And on their own, they have done and continue to do thoughtful things for each other. They donate to each other's surgeries. They give dentist recommendations. They have remote book clubs. One woman was able to leave an abusive marriage because of community support. Another decided to run for political office. Someone donated a kidney to someone else.

"We didn't have a day where it was like, 'Does anyone need a kidney? We'll pair you off,'" says Ortberg. "They found each other. They did that."

When Ortberg and I arrive at the Dear Prudence recording studio, producer Casey Miner greets us. Ortberg slips into the sound booth and is soon joined by her guest, Anna Sale, host of WNYC's Death, Sex, and Money. For 70 minutes, Sale and Ortberg dispense advice to sorry saps in sad situations.

Miner, today, is training a producer who'll be filling in for a few weeks. "The biggest engineering challenge," Miner explains to her, moving a slider down the soundboard as Ortberg speaks into the mic, "is that Mallory will peak all the time no matter what you do."

Last November, for the first post-election Dear Prudence episode, Ortberg recorded a special intro. In a shaky voice, she advised listeners to find ways to "offer some comfort and goodwill to your neighbors." Join the ACLU; donate to Planned Parenthood; reach out to local mosques. She then noted it was strange to be addressing the audience in this way. "I find myself a little bit more at a loss for words than I would have liked," she admitted.

That must have felt new to her. In my time with Ortberg, in her three-posts-a-day online life, on her voluminous Twitter feed (which she deleted soon after the election, to continued wailing and gnashing), words seem to emerge easily, eloquent even in their first-draft forms.

Midway through the post-election intro, you can hear her swallow against the mic. "I'm thinking of all of you today," she says.

You believe her.

Ortberg and The Toast have always been political, at least when it comes to the apparently controversial idea that humans should be treated well and equitably (also listened to and believed), and that injustices and inequities should be confronted.

"With the important and necessary caveat that both Nicole and I are white cis women, we felt that a site with an ostensibly feminist bent would have to take intersectionality, and our own whiteness, seriously, that the goals of feminism should not be to prioritize bringing white women up to the level of white men," says Ortberg. Those ideas were burned into The Toast from the beginning, and affected pay, hiring, and topics covered.

Since the day Donald Trump was elected president, this fact has gutted Ortberg, Cliffe, and so many others: Fifty-three percent of white women voted for the billionaire and former reality TV personality.

"I don't think there's a way to talk about this election without acknowledging that, as a group, white women chose whiteness over everything else," says Ortberg. "We spend a lot of time thinking about the ways in which we are harmed as women and almost no time thinking about the ways in which we harm others as white people. And that's huge."

Huge, but helpable. And she's struggling with how to help, in this and in general. She has some power, a voice, and platforms more mainstream than The Toast with larger audiences. (Slate, which hosts Dear Prudence, received more than 25 million unique visitors last month). She gets speaking gigs where she makes in an hour what used to she used to make in two weeks. How can she help make not only a small subset of the internet but also the world around her a genuinely better place?

Cliffe, who (along with Saxena) recently started writing for Elle, characterizes the central question of her and Ortberg's simul-semi-crisis as, "What is the point…of me?"

When Ortberg talks about/around that interrogatory, and about what comes next for her, there are pauses and rephrasings and elaborations that double back on themselves. It's the only time all day when her thoughts actually do sound draft-y.

Later that afternoon, as she settles into the couch at her house in Oakland, Ortberg concludes that she wants to be useful. Then again, "I feel like I have said 'useful' a thousand times," she adds, folding one leg under the other.

It's a nice couch, grey and comfortable. It's a nice house, with a nice yard-gate and a nice kitchen island and some nice sparkling water in the fridge. It is, by all dimensions, far from the nearly windowless studio where she began her Toast career just about three years ago.

Ortberg will turn 30 a week after our meeting. She made Forbes' "30 Under 30" list in 2015, but gone are the days of pats on the back for doing things while young. "I am no longer a rising person," Ortberg says. "But it's not like the only cycle is 'a star is born,' and you're either, like, a bright young thing or a sad James Mason."

Still, while things are going well for her, there's no inertial law of physics demanding that vector remain the same. "I can see how two or three moves in a different direction, and all this changes," she says. Maybe the second book doesn't sell. Maybe people stop asking her to speak. Maybe Slate decides she's imprudent, after all.

She doesn't seem actively jittery about that future. Turner, in fact, told me her sister is relentlessly present—centered—and that she "makes a decision and doesn't need to look back on it with regret or look ahead with anxiety."

But Ortberg is (centeredly and presently) aware that just as her life was much different, not so long ago, from how it is now, it could also become very different very quickly in the future. And she wants, when possible, to take control of how those differences look. To do good, be good, and make good. To not flow into the easiest life.

While her publisher offered a second "internet joke" book, for instance, Ortberg pitched a collection of short stories instead, which she finished writing this spring. It's called The Merry Spinster and other tales of everyday horror, and it's a departure, in depth of world creation, amount of proper punctuation, and probably audience. As she puts it, "It's not as if I can say, 'Boy, if you loved Texts from Jane Eyre, you're really going to love this set of upsetting short stories about emotional vampires.'"

But the thing about Mallory Ortberg is this: While she inspires marital fantasies in others, and has facilitated union between readers, she doesn't seem to want to be wedded to much herself—not to book genres, not to television shows, and not to beloved websites. She wants the freedom to move on, to make things hard on herself.

She'll always make jokes, though. Like this one:

"Here's your headline," she says to me as I'm leaving. "The wunderkind becomes the wundercat. She's 30 now. What else can she do?"