This week’s Editors’ Roundtable dives into Jessica Pressler’s story “A Holly Golightly for the Stripper-Embezzlement Age,” from New York magazine. A contributing editor and blogger for New York since 2007, Pressler has profiled a wide range of subjects of late, from movie star Channing Tatum (for GQ) to Goldman Sachs CEO Lloyd Blankfein. Prior to joining New York, she was a contributor to the New York Times and a staff writer at Philadelphia magazine.
Pressler’s story follows a former stripper who marries a New York financier, only to find him charged with embezzlement three years later. We spoke by phone with Pressler earlier this month about the piece. In these excerpts from our conversation, she discusses fate handing her an ending and the fascination of “these creatures that roam around the city.”
Your look at Diane Passage feels a little like the underbelly of a knight in shining armor story. Did you cast it that way in your head? How were you thinking of it as you were writing it?
I thought that she was a much more interesting character, in that she was this archetype of a kind of New York person that exists, like Holly Golightly. There have been a million examples, and they’re kind of around all the time. There’s this whole class of people where this is kind of what they do, and it’s fascinating to me. I thought she was more of an interesting character than he was. His fraud was also interesting, but he was doing it because of his own delusions of grandeur, and also because of her. That was interesting to me.
You’re sitting there with Diane and the group of businessmen at the beginning of the story, and it was almost painful to read.
It was painful to be there.
How did you choose the tone for the opening scene?
I had seen her a bunch of times, but that was definitely different. We went out a few different times, talking with each other, but that was really her in her – not her natural environment – but her doing the thing. It was like her job, her work.
How much time did you spend with her to get this story? That was the only time you were out when she was doing her thing?
It was always that we’d go out and checks would get comped mysteriously. But I spent a lot of hours with her, probably more than is evident in the story. I went to her house for a few hours one day. We went to (the strip club) Scores. The original idea was that it was going to be a very short thing, like “Let’s go to Scores with a former dancer.” Then I was like, “Actually, this is a bigger, more fun piece about this type of person.”
How did you pitch the longer story you wanted to do?
I don’t know if I used the words Holly Golighlty, or if that didn’t come up until later. There’s also this great book called “Millennium Girl” written in the ’90s about this type of person I feel has existed throughout the years. This is kind of the post-recession version of that. How did I pitch it? I don’t know. I think that I probably said that she was a type. It’s such a classic New York magazine story that it’s almost a parody.
What makes it such a great fit for the magazine?
I think the founder said the magazine is about “the parade of ambition.” So it’s a sexy story about ambition. It borders on tabloid, but it’s smart in some ways, too. That’s the quintessential New York magazine story – where you’re thinking about these creatures that roam around the city and identifying them.
You take this group of people that seem pretty loathsome at first, and you humanize them a little. As awful as the whole culture is, at the end, there’s the sense that maybe Starr and Passage really did fall in love, maybe there’s something a little touching about the way it all played out. How did you think about structuring the story?
That’s a really good question. I don’t know if I was going for loathsome at the front and then empathy at the end. During the course of the reporting, I was like, “This is a love story. It’s about these two hustlers and how they found each other.” But then they were splitting up, and that wasn’t really working out.
You know, the guys in the beginning were loathsome, though I’m sure if I had spent several hours with each of them, I would have found something in them to like. They’re people, they’re not caricatures, so they do have human qualities.
Diane in particular was really interesting to me, because she had a lot of feelings. She’s not a bad person, and she didn’t not like Ken Starr or even not love Ken Starr.
People don’t think – they think these women get together with these rich men, and they’re acting the whole time. That’s not true. You start to like whoever you’re around. You have to tolerate somebody, and then you grow to like them. I think that relationship and how it develops is interesting. In some ways, she says, it’s a more honest relationship than a lot of other relationships.
That’s not exactly true, but in some ways it is more honest. She had a lot of feelings. She had this whole life that she had imagined, that she had lived, for four years. She was a stripper who had a kid, and then was like, “Oh, whew, this is over, and I don’t have to struggle anymore,” and then got thrown right back into it. So I had empathy for her, and she was really angry about that, though she was very pleasant about it the whole time. That kind of stinks. No matter what you think of what she does or what she did, it’s a difficult situation for her to be in.
I think you make that point when she moves into the apartment near the end. When did you know that would be your closing scene?
I really thought it was going to stay a love story, so it evolved as it happened. It was kind of a moving target.
Your sense of what the story was about evolved as the story happened?
Yes. She moved into the apartment as the story was closing. It had a more ambiguous ending before. But she happened to move, and it was like, now she’s right back where she started in Times Square, which is such an iconic New York type of place. So I kind of lucked out with that. It would probably have ended in the same way, but the fact that she actually moved out of this mansion she had been in, that was useful for the story.
So for you this piece is about these New York characters and their lives. Is there anything else that you think this piece is about?
It’s obviously about New York and people who come here and have these ambitions and dreams and desires, and find themselves doing these crazy things you really wouldn’t do anywhere else. This kind of thing does exist in other big cities, but doing these outsize things with these boldface kind of names feels unique. So it’s about that and the nature of both kinds of relationships.
This is not in the piece so much, because I didn’t want to get in trouble, but I think there is this almost feminist – not feminist, but almost female power quality to the Diane Passage character, where it’s like she’s really using her femininity to boss guys around. And then it works, and they become like putty, and she’s kind of contemptuous of that. I think that’s kind of interesting, especially when these guys are jerks, like the guys in the beginning. It’s kind of cool – cool is not the right word. There’s something admirable and completely mercenary and ballsy about it, I guess. I think it’s a little about that, too.
Were there any issues with access? Did these businessmen know who you were and what you were up to?
They did, I guess. They did know who I was. I don’t know if they really knew what I was doing. I think that they don’t see themselves as characters. So they were asking, “What’s the story about?” I was like, “It’s about Diane and her life.” And they said, “Well, it’s not like there’s really a story there.” At the time, I thought maybe they were right. But I don’t think they really got what it was supposed to be. I don’t know what they thought of it. They did ask me not to use their names at all, which is why I changed them.
Diane Passage was pretty open with access, though?
She was very forthcoming. I’m not sure of her motivations, except that I think she might want to sell a book or something along those lines. She was pretty open with me, which was great. I was in touch with her pretty much constantly. I don’t think she was surprised by anything that was in the story.
Did the story change a lot between your first draft and your final version?
Actually, no – and usually I feel like it changes a lot. Structurally, it stayed pretty much the same. It was hard to get concrete information out of Diane a lot of the time. I think maybe she was a little bit nervous, and she has various legal issues, so she was not specific on a lot of things. I would have to keep calling her back and asking, “Could you be more specific?” She’s not entirely reliable, and I would have to check things with other people and stuff like that. So the details of it changed, but generally it stayed the same, because the arc of the story was so obvious.