Jonathan Ames was a fencer at Princeton University, which is also where he began writing. Since 1989 he has published three novels, four essay collections, a graphic novel, and several short stories, all of which blur the line between the fictional and real Jonathan Ames. Ames also edited Sexual Metamorphosis, a collection of memoirs on transsexuality, a subject that he explores at length in his writing. An HBO show, Bored to Death (based on his short story of the same name), airs this fall, and a film adaptation of his novel The Extra Man is currently in postproduction.

I first spoke to Ames in Iowa City in the fall of 2007, when he was a visiting professor at the University of Iowa’s Writers’ Workshop. We sat down for an interview directly after Iowa’s NonfictioNow Conference, at which Ames performed monologues. The last two years have been some of Ames’s busiest, and to chronicle his progress, we met twice more. The three discussions have been arranged here chronologically.

—Andre Perry

I. NOVEMBER 2007, IOWA CITY, A RESTAURANT

THE BELIEVER: You lay a lot of your life out there in your nonfiction work. You keep giving us all of these pieces of Jonathan Ames. There’s so much confessional going on. But what are you not showing us?

JONATHAN AMES: Well, if I could answer that question, then I would write about it. But what I’ll say is this: I guess I am still writing essays, but I think a slightly false impression comes out that I’m doing it all of the time. I wrote a column for almost three years in which I had to produce every two weeks, fifteen hundred words. So I basically came up with three books of essays—all very confessional—all of which came from this column I did for New York Press. And they published almost anything I wrote. They gave me great freedom and I kept coming out with nonfiction. I was making money and having fun with it, but since I stopped writing the column, in 2000, I’m not confessing as much.

It was in my late twenties and early thirties that I was doing, as you said, a lot of confessing. I was doing monologues onstage all the time. My first novel (I Pass Like Night, 1989) had a lot of dark material, stuff that people wouldn’t write about: prostitutes and all sorts of weird sexual behavior. That was risky, doing that stuff in my first novel and then writing it in the first person. And then after that, from 1990 to 2000, for ten years, really, I was confessional: performing a lot,...