Sex and the City
Isaac Oliver

If you live in New York there’s a chance Isaac Oliver has keenly observed you in public. If you’ve responded to him on a gay hookup app or website then the chances are even higher (and infinitely more likely to include a “dusty dildo”). In his new paperback release, Intimacy Idiot (Scribner), Oliver profiles not just the bizarre, hilarious, and outlandish encounters he has with men, but also the everyday absurdities that play out in the seemingly mundane corners of the city.

Intimacy Idiot is not all outward. Somewhere between the secret furry fetishist and the Miami disco short story writer, Oliver explores the honest self-reflection that may seem par for the course when releasing your most memorable sexual exploits to the public, but proves no less powerful. His sharp eye for human behavior is translated through an even sharper wit that will likely have you laughing out loud and thinking twice.

Ahead, we chat about the scariest hookup he’s written about, how he self-edits, and how releasing his romantic life to the world made him closer to his family. —Rodney Uhler

So let’s start with how the book came about. How did you end up with this specific set of stories?
I went to school for playwriting and was in-between ideas for plays and started a blog in that downtime. I was just sort of jotting down stories from my day or things that happened to me at my box office job, or weird things people said to me after I blew them. [Laughs] It amassed into a collection of material that I thought was fun. Not necessarily a narrative story but a cohesive in a sort of thematic way.

I started reading the pieces live in front of an audience and that helped me, as well, to shape the material and get a better sense of writing comedic pieces for an audience. It helped take them out of the realm of diary entries, things they initially started as. From there I had a pile of material and I thought maybe this could be a book and thankfully Scribner agreed.

Isaac Oliver Intimacy Idiot

One thing I loved was the mix of personal essay with these other pieces: recipes, diaries from the subway, and poems.
I really wanted it to have a city pace to it. I didn’t want it to be a standard book and that’s nothing against books of essays—because my book is one of them—but I wanted it to have sort of a collage feel and a New York clip to it, that so often we only get a minute or two window into something. I really felt strongly about it being a collage of many different kinds of pieces.

I imagine when putting together something like this, the order of the pieces is incredibly important. How did you go about deciding that?
It was a process! One of the benefits of doing my live shows is that I put together a setlist of pieces for each show, which is somewhat bespoke to each night and that helped me get a sense, just really for pacing and how to put together a thoughtful arc for an evening of material. I really applied that to the book as well, where it didn’t feel like it was following me for a chronological year of my life, per se, but I wanted the reader to feel like there is a sort of life journey that you’re going on with me.

These moments are obviously very personal. Were there any that were particularly hard for you to write and revisit?
The Big Ben story [in which a man attempts unprotected sex with Oliver] was the hardest story for me. It was certainly the scariest hookup I’ve ever had and maybe the most honest moment that has occurred between myself and a stranger, in both directions. I still don’t agree with the argument he was making to harangue me into having bareback sex with him, but he really still managed to call me out on, “Why are you doing this? Why are you hooking up with people if you’re so scared?” It was an arresting moment in my life and it still feels vivid; when I do it for a show, or when I recorded it for the audiobook, it’s an easily summoned moment for me. I do relive it a little each time.

On the flip side of that, was there a story that was fun to revisit?
The guy who turned out to be a furry; it’s a sentimental favorite for me. There’s something so sweet and strange and self-assured about him. I admire him, and I think he’s just such a singular character and person. Truly one of the strangest nights of my life was sitting there after a normal, by all accounts human, hookup, and then learning all about being a furry from him. The freedom you have from lying next to a total stranger who you probably will never see again, and just the things you feel liberated to say and that they feel liberated to say, you really have the capacity to have these conversations with people. The one I had with him was just a total delight. I’ve heard from him again because Buzzfeed ran that story and the furry community is very tuned-in so they found it pretty quickly and he had like six different furries send it to him and so we had a reunion. [Laughs] And thank god he embraced it. He’s a good sport about it.

Have you heard from any of the other people mentioned in the book?
The furry is sort of the biggest, the most major player I heard from, but I’ve probably heard from maybe five or six guys who have all been really great about it. Several of them have been like, “I never knew your name and now I do!” These aren’t hit pieces; the biggest scrutiny is reserved for myself. I’m really not out to expose people. For the most part I intended it to be flattering portrayals of these men, and luckily—knock on wood—they’ve all taken it that way. But we’ll see, who knows!

How did your family react to the book?
My family, I really lucked out with them. My parents are wonderfully supportive, they’re smart, they’re progressive, and they’ve always embraced me, and similarly have embraced [the book]. It’s not all easy for them, I think, to be reading about me being slung over someone’s knee and spanked. That may be a little rough for them, but they’re really able to separate it and see that this is my creative work and my creative life and they do their best to receive it that way first.

My mom will say things to me like, “Stop letting these guys come on your face.” [The] fact that she knows that phrase is pretty horrifying, but for better or worse has made us closer. I think they value that, and I certainly do as well.

Are you surprised by the book’s response?
When [my agent and I] were trying to sell the book, so many of the publishing houses were saying it’s too gay, it’s too specific, and it’s not going to appeal to a broader audience. I personally disagreed with them. I thought they were wrong and I still think they’re wrong. If anything, touring and doing the shows, meeting people and doing readings you see it’s not just gay people in line, or who were there. I think honesty and specificity are relatable and that’s what brings people together. People of my parents’ generation and their friends are very responsive.

That being said, were there any moments of self-censorship, times when you thought “this is too much,” or this just can’t be included?
Yes, but not because of thinking it was too much. One of the good things about writing on the internet and the immediacy of that is that you have this instant relationship with an audience and it takes away the tendency to be precious or navel gaze. It helps give you distance from your material.

A lot of things that didn’t make it into the book I cut because I thought mainly they weren’t that entertaining. I didn’t set out to write a book of every hookup I’ve ever had, because a lot of them are really boring and unremarkable and I really tried to evaluate story through the lens of “Is this remarkable?” [Laughs] Is it funny, is it interesting, is it unnerving, will this provoke a reaction in people that serves a purpose to the audience and not just to me in the telling? I cut a lot of the boring, more specific diary entry things that felt like me writing for me to get from point A to point B, but I’d rather start at point B because that’s more exciting. I suppose I could have been smarter about “is this too much,” but for me, it has been so rewarding and reaffirming to be this honest in a public forum and I think people respond in kind. I get emails and hear from people who are then sharing their stories.

Unexpected but very welcome gifts?

That sort of self-deprecating humor is often so hard to achieve. It’s a fine line, so how did you approach or think about that tone?
I guess we’re always hardest on ourselves, and my coping mechanism has always been humor. My parents are very funny and I have a lot of funny friends. It’s such an active way of engaging with the world and recalibrating what the world throws at you, and a way of owning your actions and providing perspective. I never want to take myself too seriously and I think if there’s a way to laugh at something I did, or a weakness, or a moment of ill-equipped maneuvering, or fumbling then I think I’m gonna make it! And getting other people to laugh with you is a way of pulling a community around you, about building a camaraderie and it makes me feel less alone in it, to have people laughing at it with me. It’s not always fun; there’s a time when I don’t know that I can always be the butt of my own jokes. I think there has to be something more to say than just looking for rants. Actually knowing how to maneuver through the losses is more valuable than the wins. Because there are far more losses than wins.

Who are you inspired by?
David Sedaris, always and forever. Nora Ephron, always and forever. Fran Lebowitz has only written two books but I re-read The Fran Lebowitz Reader with great frequency. George Saunders, Joan Didion, Alice Munro, Mary Oliver, Billy Collins, David Rakoff, Tina Fey, my god Tina Fey, Augusten Burroughs. Those are just a handful of people that come to mind, just people who you can tell have some skin in the game in the stories that they’re telling but who are so on top of the story too, who are in control of it and have that humor or have that rage, or that poignancy or a clinical eye—certainly Joan Didion, a surgical way of writing and approaching it. I find them all hugely inspiring.

Some of those are names that are appearing on the front and back of your book!
Yes! Hey, I’ve been lucky with what people have said, it’s very humbling. We sent David Sedaris like 12 copies of the book; no response yet. I kept saying we should just litter them along that road in England, where he picks up trash. Just toss some along his route.

Can you share what you’re doing now?
I’m trying to develop this into a TV show, or a pitch for a TV show. I would love to write another book. I kind of just want to be a sponge right now: trying to read a bunch, see a lot of things, go to a lot of places, and just sort of see what’s next. I loved writing this book, so I definitely want to write more. Definitely write another play. But yeah, just sort of gestate, be as generative as I can, which is hard! I’m the laziest writer in the world, so working on self-discipline is a whole other project.

Photo: Luke Fontana