Like early David Bowie or late Barbra Streisand, Daniel Mallory Ortberg is a multi-faceted, spinning-top type of genius — flexible, lightning-quick, complicated, unfathomable. He might play a sensible advice columnist on the internet (he took over Slate’s “Dear Prudence” column in 2015), and he might’ve played a literature-loving weirdo alien from the far reaches of space before that (he co-founded the Toast, that late, great testament to razor-sharp, freaky-ass feminism), but now a whole new universe of possibilities awaits him as he transitions from life as Mallory to life as Daniel.

Ortberg announced his transition just days before the release of his new book, The Merry Spinster: Tales of Everyday Horror, a collection of strange and wonderful short stories based on fairy-tales. Where Ortberg’s first book, Texts From Jane Eyre, delighted and beguiled like a flurry of boudoir tricks, The Merry Spinster goes much deeper, brilliantly undermining our crustiest assumptions about gender, cultural expectations, and the wide world around us. I met him last weekend in Pismo Beach, California, for a conversation about the mysteries of gender, attraction, identity, and the joys of realizing “I can want things,” as he put it.

Putting a book out is an intense experience for anyone, but it seems particularly intense in the midst of transitioning, in terms of who you are becoming now versus how the world has understood you up to this point.

It’s felt really different, for sure. I’ve felt much more anxiety and need to control and manage that. And part of what I’ve noticed in myself over this last year — you know, I took a lot of time off Twitter and spent more time on Instagram, in part because I was just developing this new obsession with my own face, trying to figure out what my new relationship to it was, and I’ve been very aware that that process was useful to me in a lot of ways. But it’s also been like, “Oh, you’re really trying to curate an image here, aren’t you?” And realizing that you’re trying is sometimes painful.

What has been your biggest fear in terms of coming out?

I think the biggest fear that I have had, which I am now not doing, was the idea of going on this book tour and not being out, just because I anticipated being asked a lot of questions like “So there’s a whole bunch of stuff about gender in your book, what’s that about?” And I’d have to say something like, “Oh, isn’t that interesting? But there’s no personal connection or anything, it’s just a thought experiment!” I was really anxious at the thought of going on a book tour and sidestepping something.

Does it sometimes feel like you’re joining the other side, the enemy, MEN?

Yeah, like, I’m taking my skills and opportunities to Cleveland. Or like “Men are good now.” Or I’m going to fix something. Or what I’m doing is in some way a commentary on ways in which men and women relate to one another, or some kind of statement on the work I’ve done before, the position I inhabited as a woman feminist. Yeah, that’s been anxiety-inducing, especially because: Men as a group? Not fantastic. White men as a group? I don’t have a sense that I will be met with safety and joy on the other side. So there have absolutely been moments when I felt like, “For real? This is it? This is what you want?”

Is there an element of your new identity that feels informed from the outside, by a group, at all? Or do you feel like you’re defining what it is internally?

I would say the group that has been the most powerful and meaningful for me in this past year is other trans people. I have had, prior to this, a few trans friends I had one-on-one relationships with. But in this past year I’ve been going to a trans support group that’s close to my house, and getting to make a lot of friends with trans men and women and non-binary people — getting together in groups, having dinner together, going to see movies. The first time I went to that group, I paced outside for 20 minutes, literally wringing my hands. That’s not a gesture I have ever consciously made. And I had this sense of “What am I doing? Am I being dramatic? Am I going to walk in there and feel totally fraudulent?”

It felt like a demon snuck into my room in the middle of the night and said, ‘What if you were kind of a guy?’ and then just left and was like, ‘No follow-up questions!’

And then you finally went in?

Yeah, I walked in. It’s always really helpful when you’ve been thinking about something alone in your room, getting upset with yourself, and then you can kind of reality-test it by experiencing other people. Because that doesn’t bring up the kind of bananas voice that you talk to yourself with. When I walked in that room, I felt like, “Everyone here looks remarkable. I want to be around them. And everything that they’re doing seems legible, understandable, reasonable, beautiful.”

That was really helpful, in showing me how to apply that to myself. Because I didn’t walk in and think any of the awful things I’d been thinking about myself toward anyone else. So it was like “Oh, this is real. This is something.”

I had kind of reached the limit of trying to work it out silently in my bedroom while refusing to clean up my floor, in protest of the fact that I don’t look like Brendan Fraser circa 1998. I literally had that thought. “I will not clean up my room until I look equal levels of Brendan Fraser Beautiful in George of the Jungle. If conditions don’t improve, I’m leaving everything I own on the floor.” Like it was the floor’s fault or something. Like I was on strike.

It’s interesting how hard it can be to tackle how you want to present yourself and feel inside. I really relate to that thing you said about Brendan Fraser, that process of holding up an ideal that confuses you, and yet feeling strongly, “This is important to me.” I’m doing that a lot right now. I’ve always been a little bit vain, but I’ve never wanted to stand out, either. And there’s so much shame wrapped up in admitting that aesthetics have always been a value of mine. So I really relate to that.

Good. I’m glad! That makes a lot of sense. There are those moments when you’re trying to tease out, “What’s the difference between something I want versus just this sort of anguish that we all have over not being incredibly famous, incredibly attractive, ten feet tall, made of gold, able to stop death and time.” Do you know what I mean? There’s no transition to being 1998-level Brendan Fraser.

Yeah. Brendan Fraser’s not there, either..

He’s not there! Time comes for everybody. It was interesting when you said you felt vain but didn’t want to stand out. Because I felt the exact opposite way. I was very, like, “I am a brain in a jar — which is fine and everyone feels that way all the time, probably — but I need to stand out.” And I think especially in terms of transitioning one of the things that’s been on my mind is that there are elements of what I do that are very much who I am, and there are also parts that are a schtick. And there are aspects of my schtick that are just not going to carry over. The things that were fun, provocative, exciting, transgressive to do as a woman are not going to be the same.

And again, it’s not like once I was a gal wunderkind and now I’m like a weird, sad goblin. But there’s very much a sense that I stopped doing a job that defined the early parts of my career. And then, I also became aware of gender dysphoria, I guess is the term for something I’d been experiencing without being conscious of what it was. In some ways it felt like a demon snuck into my room in the middle of the night and said, “What if you were kind of a guy?” and then just left and was like, “No follow-up questions!”

So I was dealing with that, and also turning 30 around that time. It was a big moment of coming to terms with fallen idols and ideas of yourself that are no longer possible, and it was painful in a lot of ways. When I first started to consciously ask a question “Am I trans?” that affected my work, my ideas for the future — it affected a lot. One day I went to sleep a businesswoman, and woke up the next morning not that, and in some ways that felt arresting. That doesn’t mean it’s a step backwards but it did feel jarring. It’s meant looking at a lot of things I wanted to skate over, and instead I had to crawl underneath them and hunch in a little den, for a long time, surrounded by all my clothes that I wouldn’t pick up off the floor.

Did you ever find yourself saying, “What if I just don’t want to move forward?”

“Bartleby, the Scrivener” myself. “I would prefer not to.”

Yeah, what if you just wanted to stay in some kind of limbo for a while.

Well, first, I don’t want to suggest that any other choices people have around their gender is in any way a commentary on mine or vice versa, or that there is any sort of “halfway” approach an individual can take in transition. But I think the thing for me that was hardest to deal with was: How do I make decisions based at least in part on feelings, when part of the reason I went to therapy was that I was alienated from my feelings a lot of the time? There was never a question of “Is this an okay thing to be for people in general?,” like what I would tell someone else to do if they described their experience to me. But it was very much a sense of “Okay, but this is me.”

So when did you decide to take action?

One turning point was in July and August, when I started talking with my close friends and my sister about it. That was scary. And then another turning point came when I started talking to the rest of my family in November, and started to access different aspects of medical transition and going to a clinic in the Bay Area. And then again, in the last couple weeks, when I decided to talk about it before the book comes out.

Why did you decide that?

It was clear to me that no, I’m not the most settled or the most confident person in the world. But I’ve spent enough time thinking and talking about this, and at this point it’s only about delay. And once my family knew what was going on and they were like, “We’re here for you. We support you. We love you,” then it felt like “Okay, sure.”

I went to sleep a businesswoman, and woke up the next morning not that.

Were there any reactions you didn’t like or were surprised by?

I would say that overall, the response I’ve gotten from people has overwhelmingly been “I’m so glad I’ve gotten to know more about you, I love you, I care about you, I’m here for you in this.” But part of what’s hard is that I don’t want anyone ever to have a reaction to me. I either want them to say, “You’re great, never change,” or “I’ve never seen you in my life, I don’t register you at all, you are covered in camouflage.” Sometimes it’s like there’s no reaction anyone could ever have that wouldn’t feel uncomfortable. Which as you know is not a possible way to be alive in the world.

I know what you mean. Where does that come from?

I don’t know, maybe it’s vulnerability. There was a real weight, even to wonderful reactions. I just feel like I’ve handed you a weapon. And even though you say “I love you, I promise I will never use this bow and arrow which has been specifically fashioned to find your heart,” you’re still holding it. So I felt like I was giving away something that could kill me. Which is a very dramatic thing to say. But that’s what it felt like. And part of what is hard about doing this is having a job that’s very outward facing and includes a big picture of my face.

Are they going to change the picture of your face?

Yes, in the next six months I’ll change my picture and my byline. The idea of changing that picture’s been terrifying, honestly. It’s like my Picture of Dorian Gray. Part of me kind of wants it to stay up forever, like that is the person you’re talking to, just this reasonable-looking lady businesswoman with a professional look on her face. Leave her there, she seems great. You know, she’s the one who got the job! But I know I will switch it, and it’s not that far off in the future.

In your career, you’ve really defined exactly what you want to do every step of the way, to the point of creating your own weird genres just to suit your own needs. But this process sounds like it took you off guard.

Yeah, you always surprise yourself. There are ways in which I feel supremely confident, like when it comes to making friends, or work stuff. But this, for me, was a thing where there was less confidence than I normally get to have. It was like, “Where has your fucking chutzpah gone, my buddy?” Where’s Barbra Streisand singing “Don’t Rain on My Parade”? Where’s the fun? And part of what’s been actually good about taking these steps toward transitioning and coming out for me is: “Oh, this is not just loss and pain and anxiety. This is exciting, thrilling, energizing, and fun.” And I get to find a different version of myself that’s not just like “Hey guys, I’m sad. I lost my gender. I don’t know where it went. Everything’s a mess.”

A big part of this last year was “Oh, shit, I think I’m going to have to transition. I can’t possibly transition.” And then, finally, “Holy shit, I get to transition? This is awesome.” And suddenly I was like, “I want things, and I am thrilled by things, and I’m energized, and I want to look at myself, and I want to pay careful attention to how this makes me feel. This is amazing.”

I love your newsletter “The Shatner Chatner.”

I have periodically talked about how I could absolutely send William Shatner 30 percent of my gender therapy bills.

Because you love William Shatner so much that you want to become him?

This is where it gets tricky. Because people will always say, when I say something like that, “Well, have you seen his Twitter feed?” And I think, Of course I am aware that William Shatner the actor is not the greatest person in the world. He is a person of a time and place who has been very wealthy and famous for very long time, with all that that implies.

Did you watch Star Trek when you were young and think that Shatner was glorious and special back then?

No, my love for the show was always bound up in its ridiculousness. Like I think I saw Galaxy Quest before I saw Star Trek. And Galaxy Quest is one of the greatest movies that was ever made.

I love that movie so much.

You know who else loves Galaxy Quest? David Mamet. He called it a perfect film. Not even a movie, a film! I think about that so much. And it’s so perfect that Tim Allen, whom I hate, of course played this person who I had this intense connection to for a really long time. Because Tim Allen was the right choice! And that hurts me to admit.

That’s part of why it works. They’re both such laughable heroes.

Kirk is just this ridiculous, wonderful, bookish lesbian who’s always wearing kicky boots and visiting ex-girlfriends on different planets and talking respectfully about their shared past and saying things like, “I’m so glad you got your Ph.D. in neuroscience now. Be well. I release you!” And I loved that, I really connected to that.

I wrote this thing once called “Captain Kirk Is a Beautiful Lesbian.” And I wrote this thing about TV characters I believed were lesbians, like Johnny Bravo from the TV show Johnny Bravo, or Ryan Atwood from The OC. Ryan Atwood is from Chino, as am I! And at one point my friend Brook said to me, “Hey, you know when you were writing that series, did you ever think that part of what you were saying was that you were a trans guy?” And I was like, “I did not think that Brook. Thank you so much for telling me. Why didn’t you say anything?” And she said, “It seemed like you were already there.” And I was like, “I was not already there, thank you very much.” But I went back and tried to read some old pieces with that question in mind, and I was like, “Oh, this is humiliating!”

What did you find?

I literally had written something about Deep Springs College. It’s a two-year college in a working ranch and only men attend. It’s a ridiculous place. And I was like “It’s a ridiculous place! But had I been born a man, I would be there right now, reading Plato with my fellows!” I mean I was putting it all out there.

Now that you’re really putting it all out there, does it change your perception of your new book a little? Do you have a new sense of “Oh, I see how this is kind of like an embossed invitation to meet the new me!”?

Oh man, I do in some ways. On the one hand, it’s very much a work of fiction. It is not a thinly veiled retelling of relationships and experiences I have had personally. And yet I also began thinking very seriously about my gender identity and the possibility of transition about halfway through writing it. And the title, the idea of a merry spinster — the idea of jolly, self-sufficient female solitude — that’s very dear to me. And in some very real ways, that’s no longer mine.

There’s a line in one of the stories in the book, Cast Your Bread Upon The Waters, where the main character – whose gender is never clarified – refers to their son, against whom they’ve been plotting murder, like this: “My son Johnnie was very beautiful, and I loved him.” It’s one of the first unmitigated statements they make about a person they very clearly loved but are trying to build a case against. Only after they’ve done the deed can they honestly say, I loved him. I don’t want to cheapen the story by saying, “Ah, yes, I too have released someone I love into the sea, it is a point-by-point allegory for transition.” But man. That merry spinster, that Toastified Mallory Ortberg — she was beautiful, and I loved her. And she is! And I do! And she is not gone, there has been no death, no act of violence, no act of disavowal or abnegation or dismissal. And yet she’s not herein the way that she was. Anyhow, it’s a good book, I think, and I’m glad we wrote it.