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Daniel Mallory Ortberg. Image via Melbourne Writers Festival (digitally altered)

Daniel Mallory Ortberg is the co-founder of The Toast and author of the books Texts From Jane Eyre (Hachette, 2016), The Merry Spinster: Tales of Everyday Horror (2018), and the forthcoming Something That May Shock and Discredit You (Simon & Schuster, February 2020). He also serves up regular guidance to Slate readers as their ‘Dear Prudence’ columnist. In 2018, before the release of The Merry Spinster, Daniel introduced himself to the world as a trans man.

As a transmasculine person I have very few masculine idols. This surprises me often. I don’t feel like I want that much: a kind heart, and great hair. Daniel delivers on both. After his recent ‘Dear Prudence: Live’ event at Melbourne Writers Festival, I met up with Daniel to talk about trans masculinity. The first thing he did was ask politely to take a photo of the tattoo on my forearm (a work by Mars Hobrecker of two naked people – masculine and feminine – both their bodies visibly trans) to send to his ​fiancée, author Grace Lavery.


Daniel Ortberg: It’s so cool. I promise I’ll only share it with Grace.

Oliver Reeson: My first question actually involves Grace!

Great, okay!

You published a conversation between the two of you on your newsletter The Shatner Chatner about ‘escaping lesbian velocity’. I made a meme for myself recently with the Drake ‘Hotline Bling’ template. It was essentially: sad Drake – ‘being misgendered female’, pleased Drake – ‘being misgendered male’. I feel guilty about this impulse sometimes, because both of those things are equally incorrect – and I think, why would I be any more upset about being referred to as a woman? Can you give me a 101 primer on the physics of lesbian velocity?

Oh, man. Absolutely. As you say, it’s deeply complicated because there are so many different types of queer community and being read. And by themselves, none of them are a problem. None of them are like, Oh, no, it would be awful if someone thought me of me this way, because they’re all wonderful. For me, one of the things that was really intriguing when I first started to transition, was that there was a pretty significant period where for the first time in my life, I was getting read as a butch woman. There are many ways in which being a somewhat effeminate trans guy and being a butch women are as different as two things can possibly be. And yet, to lots and lots of people, they look like almost exactly the same thing. It was sort of like, wow, this is the first time I’ve put a lot of really conscious thought into how I want people to read my gender, and it’s also the beginning of people misunderstanding me.

‘It was sort of like, wow, this is the first time I’ve put conscious thought into how I want people to read my gender, and it’s also the beginning of people misunderstanding me.’

In an extract from your next book Something That May Shock and Discredit You, you make light of some of the transmasculine tropes in memoir writing. You pretty much skewered my own manuscript, right down to the fact that I do have an essay about Kathy Acker and weightlifting. I hate myself.

I hate myself too. Hopefully it’s clear I wasn’t implying that everyone else who’s written about transitioning has done it wrong and I’m doing it right. I think I was referring to the ways that cis people often write about us, where if we try to describe something a little bit complicated, they will just flatten it. There was that piece in the New York Times the other day about somebody meeting up with an ex of theirs who had transitioned, and without wanting to deny that person their own experience, also wanted to acknowledge that, of course, if somebody that you used to know in one way changes later, or seems to change later, it brings up thoughts and feelings for you. But every time I was about to read the next sentence, I knew exactly what he was going to say. There’s real stuff there, but it’s flattened. It’s like, I know where you’re going and I wish I could stop you, because y’all say this every time somebody transitions.

Right. No matter how nuanced a situation might be people find it hard to resist the allure of those tropes. When I started my own transition you were just about to release The Merry Spinster and you were profiled in The Cut. You spoke about your pre-transition self, Mallory, and about, essentially, loving her. That was so necessary for me to hear at that time that I remember I cried. It’s this strange social violence that is done to trans people, with or without their consent, to imply that that person has died.

Thank you so much. But I don’t think I’m the only one. I think most of us, even the ones who talk about feeling a real disconnect with their birth name or their deadname, have some sense of continuity with ourselves. I don’t think most of us feel 100 per cent of the time that somebody died, and somebody new is here. And so, when we talk about stuff like cycles, like death, or rebirth, we’re speaking with a lot of nuance. And oftentimes that nuance gets lost when other people speak of us. It’s hard to say I feel continuity with the person known as Mallory, or I feel affection for the person that is Mallory. In some ways, I feel like she and I exist in alternate dimensions. In some ways, I feel like she’s always with me. All of that is true at the same time. I often feel like I would love to be more open about my feelings towards that version of myself, but sometimes I have to make sure: Let’s make sure you call me ‘Danny’ consistently, and then we can talk about Daniel Mallory.

You have always poked fun at masculinity in your writing, which is a fun thing to do because masculinity is ridiculous…

Absolutely, very silly.

But I wonder before your transition if you engaged with trans masculinity much. What’s it like to maintain a voice and an ideology, while also bringing in that new community who clearly mean so much to you?

I had almost no contact with transmasculine media of any kind until I started thinking about transitioning. I met one trans guy in college, and I did not meet another trans guy for another 12 years. And so I think there were lots and lots of different ways in which I engaged with maleness and with masculinity, both at The Toast and in my writing elsewhere which was very affectionate, which was very sharp, which was very, like, I don’t know why I want you to be better! Like obviously, because it would make life better and safer for a lot of people. But also this sense of like, why aren’t you doing it the way I would do it? Why aren’t all men like Channing Tatum is in the movies? And it’s specifically Channing in Magic Mike XXL, sacrificing your body to make other people happy and then leaving. Wouldn’t you just be thrilled all the time? Wouldn’t it be so nice that you would always just be in the best mood?

‘My writing about masculinity was very affectionate, very sharp – I don’t know why I want you to be better!’

Do you think as transmasculine people it’s possible to overcome our fear of male privilege? Is it inherently a ‘soft boy’ act to even try?

I think when it comes to transitioning and trans people, we all need a lot from each other. There are things that all of us share, and there are things that are unique to transmasculine people or to transfeminine people that can also depend upon the age that we transition, or what your transition involves. I think at that level conversations about male privilege start to break down. Because I think the fear is a little bit like, am I about to become the kind of person who no longer deserves or merits solidarity and community support? When I think about what I want for the trans men in my life, I think: better healthcare, support for their experiences with misogyny and sexual violence, with harassment, with self-esteem, with the ability to listen and respect our transfeminine sisters. We all have an ability to get away with things, we all have an ability to suffer, and to have our suffering ignored.

I think there’s a fear around engaging with it, because there’s no language. There is a language for talking about masculinity, and there’s a language for talking about trans masculinity, and those two things, in fact, rarely connect.

When I’ve been touring or doing work recently, I will be asked: Did you feel some conflict in transitioning from a feminist to a man? There’s that assumption. I usually feel like somebody who asks that doesn’t have many trans men in their lives. My experience transitioning has not been, I got handed a promotion, I got assigned a little posse of frat boys to run around and back me up. When I think about what the last couple of years have been like: I’ve received a lot of wonderful community support. I’ve also gotten a real uptick in being harassed on the street. I’ve had trouble accessing my medication, I’ve had to deal with the threat of violence sometimes. This is not to say like, oh, it’s been a laundry list of despair. But it’s also not been that I came out and the next day everyone started calling me ‘sir’.

‘We all have an ability to get away with things, we all have an ability to suffer, and to have our suffering ignored.’

I still have a female marker on my passport and when I was flying into America recently the flight attendants kept calling me ‘sir’ when they brought around the drinks cart. I had this weird conflict of emotion. It was like, I love you but please don’t let TSA hear you call me that.

Yeah, travel is often hard. I don’t always have bad weeks but recently I was having a period where as soon as I would leave the house I just felt kind of raw. I didn’t know how people were going to read me, or what responses I was going to get that day. I was at my limit in terms of how much I could absorb. I had gone to a Walgreens before I quit chewing nicotine gum again. The cashier asked for my ID and then just went into a (clearly well-intended) description of their feelings about trans people, about a relative of theirs who recently transitioned and what they wanted to say to that relative but couldn’t, and I just had this sense of like – I know you mean well, but I have no idea when this story is going to end. I don’t know when this is about to take a turn, because often stories like these do take a turn. I just want to buy this gum. And for this moment I wish you didn’t have this information about me.

Daniel, congratulations so much on your engagement, and also on your great hair and beautiful beard.

Thank you, it is so sparse and silly. I did not realise I could love something that was so silly.