Our second October Rountable looks at A Holly Golightly for the Stripper-Embezzlement Age,” by Jessica Pressler. Pressler introduces readers to former stripper Diane Passage, and a world in which a beautiful woman with enough ambition can get what she wants – at least for a while. The story ran last month in New York magazine and was edited by David Haskell.

Tom Shroder
Founding editor, www.storysurgeons.com

On lively writing:

Jessica Pressler produces a fun read here, and I’d like to focus on how a lot of what is “fun” is a combination of lively, original language and acute observation. Throughout, she manages to surprise the reader with tart but entirely apt images – funny because they are both irreverent and true.

Consider the first description of the subject, Diane Passage:

When she laughs, her grapefruit-tree physique bounces merrily.

It’s more original and less vulgar than “tits on a stick,” and it goes somewhere, too – between the laughter and the merry bouncing you start to be predisposed to like a not-entirely-sympathetic character.

Passage giggles again, and the ensuing undulations manage to pull Barry’s attention back from the blonde who’d just passed by.

“Ensuing undulations” works so beautifully because it is a comically high description of such a low phenomenon, very Damon Runyon-esque – but also so true: We’ve all seen enough Barrys to know that head-swivel by heart.

Passage is one of those people that it feels like New York invented, though they thrive wherever male egos and dumb money coexist.

Another great observation – a fun clash of stylish language (“though they thrive”) and straight talk (“male egos and dumb money”) that is also poetry. A repeated one-syllable, two-syllable pattern pairing male with dumb and egos with money. A small slice of language perfection.

This next passage is a great use of what is always a smart writing strategy, which is to just give the readers the sensory info they need to draw their OWN conclusions:

His friend, let’s call him Paul, a tall, paunchy private-equity manager was quiet much of the evening but has become considerably more animated after a trip to the bathroom.

Now here comes another smart idea: wringing the meaning out of things others might pass by without comment. In this case, it’s a pretentious name with a transparent marketing strategy. Here’s how Pressler handles that:

Passage moved with her son from a small walk-up to a $7 million condo on the Upper East Side in a building so sure of its fabulousness that it was called “Lux74.”

Extreme compression is yet another artifact of good writing. Here Pressler finds a way to avoid the yadda-yadda of excessive background and tell the whole story in a phrase. The compression of how the character ended up so compromised is so extreme, and so plain spoken, that it becomes delightful, and hilarious:

As a kid, she’d dreamed of becoming a pop star or a veterinarian, but she couldn’t carry a tune and was allergic to hairy animals. By the time she was 18, all she really knew was that she needed to get the hell out of Detroit.

There are lots more like this to choose from, but I’ll end on one that I love because it cuts so directly to the truth of her character, and does so in a way that makes readers look at something familiar in a new way:

“If I was you, I know what I’d do,” said a male colleague one day in 2004, when she confided her problems. He eyed her curvy figure. “I’d go straight to a strip club.”

Some women might have gone straight to human resources. But Passage is a person who considers all offers.

Maria Carrillo
Managing editor, The Virginian-Pilot

On summary and momentum:

Let’s start with the obvious – a story about a stripper is going to grab a reader’s attention more than, say, a story about a trash collector. But Jessica Pressler does some wonderful writing here, drawing out a multidimensional character and engaging us with memorable scenes and details.

I particularly loved two graphs in her story, two graphs where she breaks from the action and tightly conveys what you need to know about this woman and the era she’s living in and the place where this story unfolds.

Many writers struggle with this kind of summary. It takes understanding your subject, building connections with the reader, writing in a conversational tone, and most of all, expressing what you know with authority. It also means having the discipline to take pages and pages of notes and provide only what the reader needs to grasp necessary background and to keep him hooked.

Look at what Pressler manages to do in this graph:

Passage is one of those people that it feels like New York invented, though they thrive wherever male egos and dumb money coexist. She’s the kind of woman who is able, through physical charms, nifty tricks of persuasion, and sheer gall, to inspire men to pay for … well, everything. She’s like Holly Golightly, if Holly Golightly had to kick a guy in the nuts when she went to the powder room. Which, in postrecession New York, she might have.

Pressler describes Passage in the present, who she is and who she plays. She gets you to understand that this kind of woman needs a city like New York to really work her magic, because “male egos and dumb money” are more prevalent there than in a place like, say, Norfolk. She compares her to Golighty, Audrey Hepburn’s character from “Breakfast at Tiffany’s,” one of pop culture’s most famous female hustlers. And she moves Golighty into the modern world, into Passage’s world, with a tease about having to kick a guy in the nuts. In four sentences, you have a pretty good picture of a woman who knows how to work her assets and get what she needs.

And then there’s this graph:

But not so long ago, Passage wouldn’t have entertained the idea of sexually humiliating a man for a mere $100. She wouldn’t have been at this bar, with these guys, taking a small puff of Barry’s spit-covered Habana cigar because he’d thrust it in her face and said “Suck it.” Until quite recently, Passage was the happy protagonist of a modern-day fairy tale: A single mother who, four years ago, was plucked off the dance floor at Scores by a financier who promised to change her life. And change it he did.

Here’s where Pressler invites the reader into Passage’s past. After the earlier graph, you think well, here’s a woman who lives this life because she’s wired this way and it’s better than getting a real job. But then you find out that it’s really about survival and how Cinderella lost her prince (in a not-so-Disney version). And again, there’s a tease, wonderfully appropriate for the subject matter, but also inviting you to find out what happened. How can you not keep reading?

Those teases are particularly important. In any piece of long-form writing, every paragraph needs to build momentum. When you’re in the middle of the dramatic narrative, it’s not hard to keep your readers moving along – there’s action and dialogue and often suspense. But when you step away from those scenes, you can’t bring the story to a complete stop. You still have to keep pace.

Laurie Hertzel
Senior editor for books and special projects, Star Tribune

On how tone reflects character:

The focus of Jessica Pressler’s piece is a not-terribly-admirable character, a woman named Diane Passage who is a gold-digger. The story can make the reader feel uneasy and voyeuristic; it’s borderline tawdry, reflecting a world of hucksterism, populated by people with loose morals and a love of wealth. And it’s written in a breezy, gossipy tone that makes the writer – and the reader – feel like a part of this world. (The second-person “you” in the lede helps draw the reader in, whether he wants to be drawn in or not.)

All of this is, of course, deliberate. That glibness and breeziness camouflage Pressler’s fine reporting and eye for detail, which are the real backbone of the story. And that gum-smacking tone echoes (and thus reinforces) the larger-than-life character of Diane Passage.

Pressler did not write the piece in first person, nor did she write it precisely from Passage’s point of view. Yet the story seems to inhabit Diane, through language and sentence structure.

As a kid, she’d dreamed of becoming a pop star or a veterinarian, but she couldn’t carry a tune and was allergic to hairy animals. By the time she was 18, all she really knew was that she needed to get the hell out of Detroit.

As the story progresses, the reader encounters careless language that is used in a very deliberate way: “Great – not only was she broke, she was being publicly slut-shamed.” Or, “He was a schmoozer.” Pressler walks a fine line here, writing in Diane’s voice but with a broader perspective. That’s what makes this piece so fine – her understanding of Diane’s character, blended with her understanding of Diane’s flaws and limitations. The swagger only goes so far, and underneath you can feel the fear.

“A girl who knows what she’s doing can easily get a free dinner along with her drinks,” shows us Diane’s bravado, but it also shows the sadness of her situation, a life where she is getting by from meal to meal. (Albeit meals at fabulous restaurants.)

This swaggering tone makes Diane seem vulnerable and sad in a way that a story written in a more traditional journalistic tone cannot. There is much in this story that is hinted at, never stated directly.

Tom Huang
Sunday and enterprise editor, The Dallas Morning News

On when to let your character tell the story:

We’re taught to limit the quotes in our stories. Quotes tend to slow down the storytelling. Readers pause and step outside of the narrative flow as they “listen” to the character talk to them.

So we’re advised to select only the strongest quotes, using only those that advance the plot. We paraphrase the rest.

But Jessica Pressler veers from that guideline in her profile of Diane Passage. She quotes Passage extensively, particularly in the second half of the story. And her approach works well for this story. Here are some takeaways:

Use quotes when the protagonist is a natural-born storyteller. When Passage describes one of her clients’ unusual requests, it’s hard to imagine a narrator conveying the situation’s oddness and vulgarity in the way that Passage can.

We went into this little area and he was like, ‘First, go into the restroom and make me wait,’ ” she says. “So I went into the bathroom for like fifteen minutes and I was texting all my friends and then I came out and I kicked him in the nuts and he was like” – she drops her voice down to a meek whisper – “ ‘Thank you.’ ”

Use quotes when they reveal the protagonist’s motives and thought process. It’s clear throughout the story that Diane Passage is no dummy. She could probably achieve many other things with great success. But through her quotes, we come to see that Passage is not interested in a conventional life. Listen to how she rationalizes the life of the stripper:

During the day, I’d watch these sales people talk and jump through hoops,” she says. “And at night I’d go to work and watch these girls making $400 an hour to get people to go to rooms where nothing happens.” She widens her eyes. “Like, these girls are better than people who went to school and got master’s degrees and bachelor’s degrees.”

Use quotes when they unmask the character’s emotions. Don’t tell the reader that the protagonist is sad and disillusioned. Show it through her behavior and what she talks about. In the following quote, Passage offers Pressler a glimpse into her heart, if only briefly:

And eventually, between the dressing-room talk, the abject behavior of men on the Scores floor, and her own disappointments, Passage started to rethink her approach to dating. “I used to believe in love and romance,” she says. “But I felt like in a lot of cases I was contributing too much to my relationships. It was time,” she says, laughing, “to let someone else contribute.”

Use quotes when your protagonist’s voice exudes personality. You don’t want to overdo it, but you can enrich your story with the cadence of your character’s voice and the colorful words he or she uses. Think of how a radio story comes to life when a person with an unusual voice is interviewed. You can almost hear Passage as she describes, in her own style, the black-tie events she had to attend:

Some of those black-tie events were so fucking boring. We went to one at Blackstone? Their holiday party? I was like, I can’t believe I spent so much time getting ready for this.

Use quotes when the protagonist is both sympathetic and seriously flawed. Passage is a complicated person (as most of us are), and Pressler does a good job at humanizing her. At the same time, Pressler lets Passage hang herself with quotes that reveal her to be judgmental and hypocritical.

“He always just saw the romance,” she says now, “but that’s not how I saw it. I saw 80-year-old men with 40-year-old wives. I saw a lap dance, a blow job, a Mercedes.”

In general, you’ll want to use only your strongest quotes in storytelling. But when you’re writing about characters with larger-than-life personalities, it will make sense to let them tell a lot of their own stories.

For more on this article, read the Storyboard Q-and-A with Jessica Pressler. For full bios of the Roundtable editors, see our introductory post.

Is there a story you’d like the Roundtable to tackle? If so, you can send a link to us at contact_us@niemanstoryboard.org.

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