April 30, 2019

The Pursuit of Total Friendship: Nicole Cliffe and Daniel Mallory Ortberg

by The Cut on Tuesdays

Background show artwork for The Cut on Tuesdays

Nicole Cliffe and Daniel Mallory Ortberg met in the Hairpin comments section and quickly became long-distance friendship soulmates--they went on to start the website The Toast together. This week, they tell us about everything that's happened since they first bonded over Rebecca, answering questions like: How does a friendship change when one of you transitions? What about when one of you finds God? And who the fuck is Loretta?

Nicole Cliffe writes Slate's Care and Feeding advice column, and Daniel Mallory Ortberg writes Slate's Dear Prudence advice column.

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From the Cut and Gimlet Media, this is the Cut on Tuesdays. I’m your host, Molly Fischer.


I’m always impressed with people who are good at making friends. The ones who, as adults, can really get out there and actively befriend.

By that, I do not mean meeting someone once, suggesting you both get a drink sometime, and then--I, personally, am great at this--sort of liking their instagrams indefinitely and maybe seeing them at a party every six months. These things are nice, but these things do not tend to add up to an actual “friendship.”

Part of the trickiness is that there’s no real script for forging a friendship as an adult, the way there is for romantic relationships. You can’t just default to a standard progression of “go on dates, meet the family, move in together.” And that lack of obvious boxes to check can leave you with questions. Like: Are we the kind of friends who get birthday presents for each other, and, if so, do we get nice birthday presents or joke birthday presents? And did she “get it” when I sent a clown emoji, or was that just weird?

Then there are the bigger questions, the serious ones:

DANNY: Is there something that I can do or think or experience or want that would make my friend embarrassed of me or turn away from me or not want to know more about me or consider me a liability or miss the version of myself that used to exist and prefer that version over me now?

That’s Daniel Mallory Ortberg. And I think he’s getting at one of the reasons that friendship can leave you feeling so vulnerable. If you think you’ve found a person who’s somehow just like you, what happens when one of you changes?

<<MUX IN>>

This week, we’re talking to Daniel and his best friend, Nicole Cliffe, about what it’s like to make and remake a friendship when your friend is going through enormous changes--the kind of changes that fundamentally alter the way you move through the world.

If the names Cliffe and Ortberg sound familiar, it’s because you’ve almost certainly seen them on the internet.  Nicole’s a nerve center of online social life, the kind of person who can tweet a casual question and make it appear in Twitter’s trending topics. Daniel perfected a flavor of internet humor that combined classic books, text messages, and jokes about clueless medieval monks. And--a quick note--you might have heard of Daniel when he was writing under the name Mallory--he transitioned a little while back, which we’ll get to later. Anyway, they were the co-founders of the website the Toast, and they’re two people who have lived very much online.


It was online that they first found each other. Nicole was an editor at The Hairpin, and Daniel was but a humble commenter. Or, less a humble commenter than a virtuoso all-star commenter, whose contributions quickly caught Nicole’s eye. They were funny and weird and kind of mean, but not too mean. The two of them started talking, and pretty soon they wanted to hang out IRL—but Nicole lived with her husband and kid in Utah, and Daniel lived in California. So they couldn’t just grab a drink after work. This was going to be a high-stakes first encounter, requiring air travel.


NICOLE: When Danny first came to visit we had this classic thing where we were like, "Let's watch Rebecca."


Rebecca is an almost three-hour long movie from 1940 about a woman falling in love with a fancy man then being menaced by his malevolent housekeeper. It is not everyone’s idea of an obvious new-friend fun time, but it was very much Danny’s, and Nicole’s too.

NICOLE: the rest of the weekend we just spoke as Joan Fontaine in Rebecca to each other. "

DANNY: I was just so immediately clear that we did love doing that kind of play together, like finding the right note for Joan Fontaine, which would always be like tremulous, anxious, and desperate, which is to say ourselves dating men at 21.

NICOLE: "Oh, I'm so terribly happy, Maxim. Are you happy? Maxim."

DANNY: And then with... Oh my God, why can't I remember the name of the most famous actor of all time. Nicole, help me out here. Who's the man in Rebecca?

NICOLE: Laurence Olivier.

DANNY: Thank you. Laurence Olivier. And he would be just like lazily crushing your dreams in every response so like, "I've never been happy. How dare you. How dare you accuse me of happiness."

NICOLE: In my life!

DANNY: Yeah, yeah

NICOLE: we were each constantly gauging to see if the other person was still having fun with this-

DANNY: Mm-hmm (affirmative)-

NICOLE: ... or if one of us had crossed the line into becoming tedious or too needy and that never happened. And that's never happened in the ensuing 11 years or whatever. It's just neither of us have ever hit that point with each other, which I think is very rare and very magical.

<< JOAN FONTAINE: If you should find one perfect place or thing or person, you should stick to it. Do you think that’s very silly?

LAURENCE OLIVIER: Not all, I’m a firm believer in that myself.>>

<<MUX IN>>

That kind of magical, one-perfect-person friendship can feel like a throwback to childhood, when making a friend meant wanting to hang out nonstop. Like, “Let’s have a sleepover, and then another sleepover, and then another sleepover after that one if our moms will let us.” Granted, the nonstop hangout is often less feasible in adulthood.

DANNY:  I wanted to be around her as much as possible. I wanted to impress her as much as possible. I wanted to make sure that she felt the same way about me that I did about her and so that's always such a delicate dance, especially when it's part of friendship where you already have like Nicole at this point already had a husband and a child so it wasn't like we were living across the street from one another and we could dedicate all of our spare time to going out and getting coffee and shooting the shit.

MOLLY: Yeah.

DANNY: And I was also very clear on like I loved and took great joy in the life that she had already built for herself so it was more a question of like am I Cody from Step By Step, the weird guy who lives over the garage. That would be ideal.

For Daniel, especially, becoming Nicole’s friend meant finding a way to fit into her life. Nicole had a family; she had a home and responsibilities and routines.

DANNY: There was a long time when I could never remember which of Nicole's pans were not meant to be scoured and so I would often incorrectly scour a pan that should never be scoured and so it was sort of like part of the task of the friendship was learning the house rules so that I was a net positive for household tasks. You know like when you're a frequent quest and you don't want to make life more difficult. Anyways -

One of the earlier times when I was visiting when Denali was still alive and Denali was this wonderful beloved old dog of Steve's, Nicole's husband. He'd had Denali when they had met. Denali was like... Denali was his Danny, right?

NICOLE: Mm-hmm (affirmative)-

DANNY: This was a long and important relationship. And I am often...


DANNY: Anyways, I'd woken up early one morning, which is kind of unusual, and Denali had just had one of those end of life dog accidents all over the kitchen.


DANNY:  It was, you know, a sea. And I was cleaning it up when Steve came downstairs, which is... Or was it Steve? It was somebody saw me, which is just, you know.

NICOLE: It was Steve.

DANNY: It was just this moment that it was like did I do right? Am I part? Is this good? And it was just this kind of moment where Steve did that sort of like grave nod of like male approval like yes. You've earned the right.

MOLLY: Welcome.

DANNY: Right. Like I will fight a pack of wolves if they ever attack. You will be under the aegis of my protection now. I was like, "Thank you, Steve."

NICOLE: One of the greatest impediments to female friendships and male friendships and any other forms of friendship that one gets is if your relationship with their partner becomes bad or is in any way, like if there's a power play in dynamic and I think that moment Steve was just like, "Danny's in.”

Once they were unquestionably friends, they decided to take what was, for them, the obvious next step: they started a website together. In a post introducing the site, they wrote: “The Toast is a daily blog that publishes features on everything from literary characters that never were to female pickpockets of Gold Rush-era San Francisco. The Toast is one of those mass-market science fiction paperbacks ... with drawings of women in long white robes standing in front of a horizon with two or three moons on the cover. The Toast is a long email chain about force-ranking the Mitford sisters.”

In other words, the Toast was their friendship. It was their inside jokes and obsessions, opened up to a public audience. They even called their LLC Manderley--a reference to Rebecca, the movie they’d first bonded over.

And even though The Toast was proudly niche, it found a devoted audience--Daniel and Nicole’s enthusiasm was infectious. The site was a kind of monument to platonic bonds.

DANNY: Nicole I'm looking through our archives right now and you and I one time wrote together a piece that was some version of how to out wait your friend's boyfriend.

NICOLE: Yes. It was so good.

DANNY: Like, just like you know that relationship exactly, and sometimes you just have to outwait that guy, and here's how you sabotage him. Act blandly surprised whenever she asks if she can bring him along to something, no matter how long they've been together. "Oh, Dave's coming too? Sure. That's fine."

DANNY: Learn exactly one thing about him. Make that the subject of conversation whenever you see him. It will not be necessary to learn two things. "I think it's really important for a man to recognize how magnificent you are, Meredith. I'm glad you think Derek sees that in you."

DANNY:  Avoid criticizing him at all costs, but if you must, put the word, "It's endearing how" before your criticism, so he takes it as a compliment while the seeds of doubt are planted carefully in her mind. "He has such great energy. I love how whenever I run into them, he's at the center of this little clump of women, just regaling them with stories."

They wrote that Toast piece back when Danny’s byline was Mallory Ortberg. And the Toast, in its idiosyncratic way, was a women’s website—being women who ran a website for women was what they did.

DANNY: When we became friends, it was very, very, very much on the foundation of like, "This is a female friendship. We are two women who are friends. This isn't just like our connection, but it's also something we want to base a career on, and kind of a sense of identity with like women having relationships that aren't about marriage or men." That just also had a lot to do with our shared experience as women. And as I came to understand myself as a trans person over time, you know, that was not something that I had known consciously when I became friends with Nicole, I remember like joking with Nicole. Like, at one point, I had kind of thought, "Nicole's probably going to transition too because we have so much in common."

DANNY: Like, there was a little part of me that was genuinely surprised, like, "We're not doing this one together?"

Coming up: Danny hopes that, if Nicole isn’t going to transition too, at least she’ll turn out to be psychic.

DANNY: And of course, in my mind, I'm like, "Oh, yeah. Nicole gets it. We're on the same page here."

MOLLY: Uh-huh (affirmative).

NICOLE: No, Nicole did not get it. I don't pick up on hints.”

That’s after the break.


Welcome back to the Cut on Tuesdays.

This week, we’re talking with Nicole Cliffe and Daniel Mallory Ortberg. They’re two best friends who met online, and eventually translated their friendship into a cultishly beloved women’s website called the Toast. When we left off, they were talking about what happened when Danny began to think about transitioning. He was grappling with all kinds of questions--and one of them was how transition might affect his relationship with Nicole.

DANNY: Like, there was a little part of me that was genuinely surprised, like, "We're not doing this one together?" And then, the kind of other aspect of that was like, "How do I do this without losing part of that connection?" How do I make that clear that was real? You know, like, we didn't make that up, or I wasn't just trying to live up to some ideal? That was a real and true part of who I was and the story of our friendship.

They’re able to talk through all this stuff now, but it took them a while to get there. Just finding the right way to bring up something as big as transition felt like a challenge. Along the way, there were many dropped hints that did not get picked up.

NICOLE: I remember Danny showed me this Instagram page, which I immediately added because it's very beautiful. But it's like, it's FTM transition.

MOLLY: Mm-hmm (affirmative).

NICOLE: So, just before and after pics, essentially. Danny would be like, you know, "Oh, my gosh. He looks so amazing. How cool is this?" I was just in my head, just like, "Yeah, Danny definitely thinks that like trans dudes are super cute. That's great."

MOLLY: Just filing that away, yeah.

NICOLE: Just filing that away. And I think it was two years before we had any conversation, any conversation whatsoever that there might have been more to that.

DANNY: And of course, in my mind, I'm like, "Oh, yeah. Nicole gets it. We're on the same page here."

MOLLY: Uh-huh (affirmative).

NICOLE: No, Nicole did not get it. I don't pick up on hints.

DANNY:  Right.

NICOLE: You know, my entire family is neuro-atypical, and I will never really pick up a hint. I cannot tell if people are lying to me. Like, this is just something, which is a real issue for me in my life. I think that probably for months, Danny had been attempting to get me to figure out on my own. I'm sure that what Danny wanted very much was for me to ask, and I failed to do that, because I am a dumbass who does not put things together. Hints or otherwise. So, what Danny eventually did, I think it was a text message that was just, "I'm sure you've noticed that I've been thinking a lot about gender recently, and I don't know what any of that means, but if you wanted to periodically call me a beautiful boy, that would be good for me."

DANNY: That is so me. Oh my God. Like, a lot of careful couching and then a diva-ish request to be called beautiful. That is extremely on brand, and I believe it completely.

NICOLE:  And I was like, "Oh, oh of course." And then like lay on my bed for an hour being like, "Oh, okay. Okay. This is happening. This is something." I felt bad later that I had been like a poor friend in that there are things I should have noticed and realizing that like Danny had been talking about this with other people who weren't me, and I felt such jealousy so briefly in that moment.

DANNY: One of the things that felt hard was//I want to be able to share things with you, not just because I think you will immediately say, "Me too. I feel that way all the time." And I think that was kind of one of the first times that we kind of bumped up against how do we talk about things where we don't believe right away we're going to be like, "Yes, you and me. Friendship magic, same as before." We intuitively and immediately understand one another. How do we relate to each other when we have to talk stuff out?


For a lot of their friendship, Danny had been figuring out how to work around Nicole’s life. Now, though, he was reinventing himself. And Nicole found herself in a new position, trying to understand everything that was going on in Danny’s life.

For example, Danny had gotten close to a friend on the West Coast named Grace.

NICOLE: Grace had like that, that thing I've always wanted, which is physical proximity to you. You know, like that was like something that, that Grace had access to and I'm like, Oh my God, Grace is going to have all this time, you know, with Danny to develop this kind of like intimacy.

When Grace first came up in conversation, she was using a different name--because she was transitioning, too. From two states away, without that physical proximity, Nicole tried to keep up.

NICOLE: Because Danny sometimes forgets to tell me things because we're very close and so he assumes I know things. I remember that, you know, Danny's sister was giving birth. Everything was like hugely up in the air and Danny was like, yes, Grace and I are on our way. And I was like, who the fuck is Grace? Because Danny had forgotten to tell me that? Like this person, I was jealous. I've had transitioned and was also now the sort of person who would be driving to the hospital with Danny's family to be there for this incredibly important fraught moment. Yeah.

DANNY:  Part of the reason that I laughed so hard at this was one of the sort of like recurring gags in our relationship is that after Nicole's beautiful third child was born, Nicole was texting me about her and had mentioned like in the, in a way that it was like you, you talk about a new baby, like they're a house guest sometimes and it's kind of funny. Okay. And I like took that at face value and I just like had not retained for the fact that her beautiful baby was named Loretta. So I thought Nicole was just like apropos of nothing talking to me about some friend of Steve's who was staying in the week and I just typed back, who the fuck is Loretta? All Nicole had to say was my beautiful darling new child and I felt like a monster for months and months on end. So we say it to one another often to really drive home. The point that loving me is sometimes a complicated task and that my memory is not all that it should be.

MOLLY: Who the fuck is Loretta

Loretta and Grace were newcomers on the scene. And because Loretta was a baby, things were more complicated in the latter case.

DANNY: You know, one of the things that was tricky I think is that when I met Nicole, she was married and had a kid. It was very clear like who you know, who is she committed to, who are the other like primary relationships in her life. And when we we met, I was like, you know, very much unattached. And so there was this sort of like, I was able to kind of shaped my life in some ways around their family in ways that necessarily were going to change. Like regardless of whether or not I was in a romantic relationship of my own, but just as I developed my own more adult, like longterm primary relationships in addition to my relationship with Nicole. So there was always going to be that kind of question of who are my people in addition to Nicole?, and so I would often feel like with both Grace and Nicole, like I don't know how to incorporate these two relationships together and I would, I would just often feel like really eager and anxious or I hope everyone, like I, you know how it like when you're like in seventh grade and you're like, well this is my best friend, but I'm not her best friend.

Nicole also had an experience of feeling vulnerable and uncertain in her friendship with Danny, thanks to the presence of someone new in her life… In her case, however, that someone was Jesus.

NICOLE The moment in which I was most fearful that something was about to happen to like drastically change our friendship was ages before Danny was even thinking about transitioning, but it's when I became a Christian.

Nicole was a life-long atheist who came to religion on her own, through reading and a lot of private thought. In an essay she wrote for Christianity Today a while back, she said of her conversion: “It has complicated all of my relationships, changed how I feel about money, messed up my public persona, and made me wonder if I should be on Twitter at all. Obviously, it’s been very beautiful.”

Danny, meanwhile, had grown up in the church, with parents who were pastors. He’d had to negotiate his own relationship to faith.  And Nicole had no idea what he’d think if she casually told him she’d asked Christ into her heart.

NICOLE: and Danny had been visiting for like a week and I hadn't said it. And when Danny got there and I said something very like sort of half joking half seriously about having like found the Lord and Danny said nothing. And so I was like, "Okay, this is not something Danny wants to talk about. That's great."

And then literally 20 minutes before we had to leave for the airport, Danny said, "When you said that, what did you mean?" And then we talked about it like literally as I was loading Danny into a lyft or whatever. But I was - I was afraid that I was dropping a bomb into a situation.

Danny had written a piece about not believing in God anymore for Gawker some years previously-

DANNY: God, what a sentence. I'm  so sorry. I promise it's not as bad as it sounds, but-

NICOLE: No, I remember thinking like I didn't want to have this thing that Danny couldn't or wouldn't or would find difficult to engage with, that this was going to be something that he would miss out on part of me in this way because it's such an important part of my life. Which I look back on, but now I'm like, there's nothing I could do. There's no ridiculous thing I could do that would separate me from Danny


DANNY: I think for both of us going through those moments and having those conversations and realizing and seeing the ways in which our friendship did not need to rely being the same people that we had been previously in order to flourish and thrive and be real and meaningful and I think, my love for Nicole is not rooted in, I can predict what she's gonna say or do or think or want, but it's rooted in her being Nicole.

And that only she kind of understands what that means and only she gets to decide what that looks like next. My joy is that I get to experience that with her. Not like I get to keep tabs on what I think she's going to do next or what's okay for her to do next. That makes it sound very just like abstract and what I really just mean it's like the project that is Nicole is always changing just like me.

The project that Danny and Nicole started together, The Toast, shut down after a three-year run--it was much mourned, and some of its most diehard readers actually started a private slack group so they could all stay in touch. Nicole and Danny, meanwhile, found a way to keep working alongside each other: They’ve both got advice columns at Slate, and once a week they choose a letter to answer together.

But their real project--the project of figuring out how to stay in each other’s lives, even as things change--is still in progress. Last year, Danny and Grace got engaged. And now--like Nicole’s husband, Steve--Grace is a cherished part of the Danny-and-Nicole friendship universe.

NICOLE: I was so happy when Danny and Grace, who is now his fiance, became romantically involved.

DANNY: You almost said "lovers." I could tell.

NICOLE: Lovers. No, it was-

DANNY: Became lovers. You monster.

NICOLE: It was very important to me. ////

NICOLE: Like Grace and I text separately, we have our own relationship. And even if something were to happen to Danny and Grace, like as a, as a couple Grace is in like Grace's on the team, there's no, there's no going back from that.

DANNY: And you're not trying to out wait anybody.

NICOLE: Yeah, I was not.

As we were working on this episode with Danny and Nicole, the Cut on Tuesdays team got to talking about how--just in general--we’re always interested in hearing friends who work together talk about how they do what they do... the way their relationship shapes the work they make, and vice versa. So we’re thinking we want to turn these interviews with collaborator-friends into a semi-regular thing. And if you too are interested in conversations with brilliant friends, you should stay tuned--we’ll have more for you soon.

In Danny and Nicole’s case, the feeling of their first meeting has never quite gone away. That experience of finding someone else who was just as committed to the bit, to getting the Joan Fontaine voice the exact right amount of tremulous--they’re still delighted by it, and they don’t take it for granted.

NICOLE:  I remember I felt a little vulnerable sending this text, which was ridiculous because we'd been best friends forever, but I said, "I am always still trying to impress you." And Danny was like, "This is also true for me." I think in that exchange both probably I could relax about that a little. But also the joy of knowing that like we are still always on a first date in that respect.

That’s it for this week’s show… We’ll see you next Tuesday.