Daniel Mallory Ortberg: You mentioned that some of the pieces in this book were longer essays and some were snippets. There was one such snippet that I wanted so badly not only to be the longest essay in the book, but possibly your entire next book; it’s the one about the Enneagram. Can you talk about that?

Sloane Crosley: I’ll walk you through as much as I can, although the whole point of the essay is that I’m sort of a dilettante, and the people I’m with are experts. Basically, in the essay I describe that numerology and astrology are like the back of a cereal box compared to this thing. You’re asked all these very detailed questions beyond basic personality questions, and through this sort of pentagram thing (which sounds like the devil’s work, but okay), they figure out your number on a scale of one to nine. The essay is about my two coworkers who taught me about mine.

DMO: They did something that seems to happen any time someone introduces you to astrology, or Myers-Briggs, or the Enneagram. They tell you what they think you are, you take a test and confirm it, and then later if you do something they don’t like, they tell you that they are no longer sure that’s what you are. You had your nine-ness taken from you and you were given a six.

SC: I was given a six! Because I had a fight with my coworker, and he was like, “You know, I think you might be more of a six.” And I was like, “Oh.” And then he said, “Hitler was a six.”

DMO: It’s like Scientology. If someone joins before you, they are the authority on it. So if someone’s known their Enneagram number longer than you’ve known yours, they can take yours away.

SC: It extends even deeper than that, because they’re from Boulder, and they went to Bard. Therefore, they were authorities about anything from what my grandmother might have deemed the “hippie-sphere.” That’s where they hailed from. There’s an essay that follows this about me going to write in Sonoma and befriending some pot-smoking swingers because I was hungry and they had food.

DMO: California shows up a lot in this book.

SC: California shows up a lot. This area — like, Santa Rosa — shows up a lot.

DMO: California pops up in that a long lost relative has fled there, or an old roommate has decamped for it, or you’re like, “Maybe I’ll become a different kind of person here.” California shows up as the B-plot line of every season in this book.

SC: I think the greatest compliment I ever received from the friend who lived in Sonoma was when he told me, “You know, you don’t really seem like you’re from New York. I always thought you were from around here.” But I’m always so wound up! I’m always fighting it. In the essay I talk about how I thought I had to be a new version of myself. How peaceful it would be at six in the morning to wake up and walk to the bridge, how lovely it would be to smell the air and see the — whatever. I did take this walk one morning. There was a piece of graffiti on the bridge, a John Steinbeck quote that said something like, “No good thing comes . . .” Or, “If it’s natural, it comes . . . don’t rush?” The reason I can’t remember the exact words is because it seems like something anyone would say, but John Steinbeck’s name is stuck to the back of it. I was just so annoyed. Can you imagine running through an airport or catching a movie with that guy?

DMO: Very much the way in which California functions in this book is that it doesn’t work.

SC: It doesn’t work for me. I think it works in general.

DMO: As I read through some of the interviews you’ve done, one of the things I noticed was this perception — and I don’t know if you feel this way or not — that there are fewer jokes per square inch in this book. There is this narrative that as you become a more mature writer, you don’t get to be as funny. I’m curious: does that feel true, or is that the kind of thing you just have to say when you’re on a fourth book? Do you feel that fewer jokes means more maturity?

SC: No. The other night I made this horrible joke and everyone laughed at it, and I was like, I can’t believe you guys just laughed at that. What’s wrong with you? And this man came up to me afterwards and said, “We’re in the age of Trump, we’re living under this fascist regime where everything is so extreme, and now you can make that joke, but before you probably couldn’t.” And I was like, Oh, no, I could before. There are certain things that are untouched by this, and my irreverence and my desire to grab every joke I can find has not changed. I think it’s not about maturity so much, but just having a better sense of when jokes are blocking what the piece is about. Hopefully there’s some sort of heart and some tentacle of actual narrative sticking out from them. Too many jokes would be distracting.

DMO: I was thinking of the chapter about your neighbor Jared, who, by the way, I could write a book about now. I have so many feelings about Jared. I think about him most of the time now.

SC: I do too. It was the only name that I’ve ever had difficulty changing for legal reasons. Everything else is really easy, if not fun. Like, you seem like an X, I get to rename you. But his name, from his parents and his friends calling his name, is so seared into my brain, that I actually fought with the lawyer about keeping it.

DMO: The whole thing is a catalogue of all the things Jared has ever said that you’ve ever overheard, and all of the ways that he simultaneously baffles and infuriates and inspires envy. There’s that moment you see him with his friends and you’ve been debating whether you want to yell at them. They go inside, and he dips a friend of his, while they’re grabbing ice, and you have this moment of, oh my god, I’m so in love with these people! And that’s so real. That chapter isn’t just a list of all the ways your shitty neighbor is frustrating. It’s like, I don’t know what to do with this person who lives so close to me, and I know so many things about, and who drives me absolutely insane. I feel like that guy is why I transitioned. Does that make any sense?

SC: That makes no sense!

DMO: The description of this person who is near me and so far and I love them and I hate them and they won’t shut up and I keep hearing their name. But within myself. I am the Jared within.

SC: That essay is . . . I’m sort of waiting for him to grow up, and hopefully that makes it more than just complaining about my neighbor, though it’s plenty of that. It’s really about aging, coming to terms with your own youth. I had this ridiculous idea that if I waited long enough, he would just go to college. But what happens while I’m waiting? Four years pass, and I become older. He can’t catch up with me. And he has a younger sibling that he trained. I take extreme measures to get this kid to shut up that are a little bit beyond calling 3-1-1 and knocking on the door.

DMO: You make some purchases.

SC: I buy a crossbow. Just kidding.

DMO: We were talking about this a little bit earlier. There were some interesting moments of a shared experience. We have both injected hormones into our bodies. What was it like for you?

SC: The last chapter is a big essay about fertility and the pressure to be a mom and all that stuff, and I was hesitant to jump in on that just because I felt like I’d read so many articles — or avoided reading so many articles — on this topic, and I was like, what do I have to say about this stuff? But then it’s like, whatever, people still write books about Lincoln. The point is that part of the humor is the detail of the medical stuff, of injecting the shots. At one point I describe the different needles you use for various things, and you have to get over your squeamishness around needles very quickly. I don’t know about you, but this happened to me. There was a needle to put drugs in, and a needle to take drugs out, and those are two different needles. Once, with a long one that you use to take drugs out, I sliced my finger open, and it was such a clean cut that it took a while to get used to itself before it started bleeding.

DMO: Like when you get your head cut off in a movie?

SC: Exactly. Like the many times I’ve had my head chopped off. Sometimes I would somehow miss a few injections and I would have the wrong amount of drugs left over afterwards, and it felt like putting together an Ikea dresser and having extra screws, like, is this gonna hold up? Why do I have these extra lugnuts here? But it’s like injecting this dresser into your body, so it’s a little different. I don’t know if you’ve had accidents.

DMO: I’ve definitely had accidents. The first time I injected at home, I was given a different size barrel than I was used to, and I was like, this seems like the same amount as before. The same numbers I was used to, but with the decimal points in different places. So basically I tried to inject roughly 400% the amount in the vial. So it exploded a little bit, and did not work out. So I just cried a little bit and tried again.

SC: There’s a lot of crying that goes on. When I cut myself like that, I cried, which is kind of normal when you slice your finger open. What’s not normal is that it took me an hour to stop. Even when I was very much over it personally, I still could not stop crying. I was laughing like a psychotic clown in the mirror.

DMO: You write that part of what’s stressful in this moment is that you’re not going in with a really strong sense that you absolutely want to have a biological child, so these are the steps you gotta take to make it happen in the next two years. But for me, when I went in to start doing injections of testosterone, they were like hey, by the way, this will affect your fertility, so if you plan on having biological children, you should freeze your eggs before you come back in next week. And I was just like wow, I didn’t think of these things as related. I’d been figuring this one thing out, and then suddenly I was presented with this other question like, do you want to think about this now? And I’m like . . . no?

SC: The whole point of the exercise is to buy yourself out of having to answer that question, right? You don’t have to think about it. Eventually you do, but . . . It speaks to the way we think about our bodies in general. If you inject something into your bloodstream it’ll go everywhere, but I have so deeply internalized the idea that motherhood is separate from the rest of me, that when I heard you say that, I was like, why couldn’t you have both of those at once? As if they weren’t going to commingle in your entire body and make you completely insane.

DMO: In the essay about being diagnosed with Meniere’s, you talk about not knowing how you want to write about illness, and you relate it to travel writing. So it connects to that chapter where you have a rough time on a volcano.

SC: There are writers who explore themes over the course of multiple books — like that person is very interested in Judaism, or they’re very interested in relationships, whatever. But when you have a collection of essays, if they’re not already pre-published — and these aren’t; they’re mostly brand new — they’re written along the same timeline, so they’re going to have weird subliminal overlaps. And some of them, I caught. I’d be like, this is weird, if anyone’s holding a fruit it’s always a mango. And those, I just edited out. But some, like this one, I left in as a little callback to the former reference.

DMO: I love the idea of relating writing about illness to travel writing, where it’s hard to get a response. When you write about travel, people can think, I want to go there. But when writing about illness, you’re visiting a country other people can’t and don’t want to visit.

SC: Yeah, it’s like North Korea. And yet it feels the same when you’re in it. Every travel story has a much bigger story behind it, both in terms of what is edited out for space — like, oh we don’t have time to include this winery or this peacock you saw, or whatever — and also a bigger narrative, like the writer missed their flight and had this crazy, harrowing experience, or had fraught texts with their mother or ex-boyfriend, or something like that. But those extra details that give so much color to the idea of traveling do not work for illness. The name of the game is not so much to take this big giant world we live in and narrow it down to a manageable size, but to take medical writing and explode it in a way that’s interesting, that’s not just like, woe is me, the self-pitying thing you can fall into. But it does feel like I’m using the same muscle.

DMO: You mention feeling really anxious about writing that appears wallowing. Do you have a strategy for catching that?

SC: As I’ve evolved, I’ve become more interested in making objectively dark things funny. That essay I just read was one of the few moments of real physical comedy, being in that head-donut and watching that dog having a seizure, and not being able to move while it was moving quite a bit. And that was really cinematic. There’s the essay about being diagnosed with an inner ear thing. There’s a theme — maybe it’s the theme of aging — that connects with some of the other things we were talking about. Like that I have Meniere’s too early. Most people who are diagnosed in their 60s or older.

DMO: The easy way to talk about dark humor, or making terrible things funny, is to say that you’re making light of it. And certainly that’s one way it can manifest, but that’s not what you’re doing. What does it feel like to be sort of trapped, but sort of by choice, and for someone else to be moving while not wanting to?

SC: You recognize your own ridiculousness. If you’ve ever broken down by yourself to the point where you actually, genuinely have to sit on the floor and cry, isn’t there a part of you that is like, what? I can’t believe this is happening. Or when something is so bad, you feel a little bit outside of yourself because you’re sort of disconnected and you’re watching this happening and you’re anticipating how bad the repercussions are gonna be. For humor writing, you just make that voice funny. But it’s the same principle, where you’re watching it happen. These essays tend to end on not-that-funny notes. They tend to end on some sort of sincere note.

DMO: And the thing you were just talking about, that question of generational drift, or that question of am I young or old in relation to these people, am I a parental figure or a child figure?

SC: Should I dress up to tell them to shut up? I did.

DMO: That question of, in what capacity can I tell these teenagers to stop partying? It was clear you weren’t going to be able to be a parent.

SC: I’m still so mad that I thought you were going to say, “It was clear you couldn’t poison them.”

DMO: That would be, at the very least, difficult. But that’s a question throughout the book: what generation am I a part of? Does my generation fit into the world around us? Do we make sense to the world, does the world make sense to us? Are we old? Are we young? And that moment you go for the image of an attractive authority figure, like an attractive teacher or an aunt you’re not really related to — you talk about doing the scooped neck and the long hair and the lipstick, so that you were trying to both soften what you were doing and also —

SC: Be like, I’m going out, too. While I’m just at home, eating pizza and watching The Crown. I’m in-between generations.

DMO: You said “Generation Catalano” previously.

SC: That’s not mine. I don’t consider myself a millennial, but I wonder if that’s actually a factual thing, or if it’s just the bad rap. I don’t know what that is. I think it’s actually factual though. I’m ‘78. At some point, I started to realize that I’m in this weird trapped generation where I’m not reacting to things like a twenty-five-year-old would react, but it’s hard to say anything about that, because I also don’t want to align with myself with Angela Lansbury or the country of France.

DMO: Sometimes we don’t realize there’s been that many generational shifts until it becomes clear that there is a cohort of people that have come to some sort of consensus that you have not come to, and you realize oh, I’m not twenty-five anymore. I don’t even know any twenty-five-year-olds.

SC: I know some!

DMO: Oh? Good! Great! What are they like?

SC: Ten fingers, ten toes. Some of them have jobs.

DMO: There’s that question of, do I react against this generation? Do I do that sort of, this generation is going to fix everything, in that way that people say when they’re about to retire from doing things.

SC: At some point in “Outdoor Voices,” Jared’s friend, who’s having trouble making friends in college, is visiting, and Jared’s mother asks her, “How’s it going?” And she’s like, “Oh, I haven’t really found my friend group yet.” And the mother says, “Keep at it.” She says, “You guys are our future,” and I’m like, oh god, no.