The first time I hung out with a millionaire was in Three Guys Restaurant, a lackluster, no-frills diner on Madison Avenue. It was a chilly, early winter day. She, the millionaire, ordered green tea and I asked for coffee. We talked about her soon-to-launch line of cruelty-free handbags; about hanging out with Andy Warhol, which is what she did in her twenties instead of going to college; and about “critters,” meaning animals, which she adores and has many of (eight dogs at the time). Our conversation was interrupted briefly when a homeless man walked in to panhandle; the owner politely walked him out and returned with a wan smile. At this, the millionaire said, “I love this place. It’s been here forever. Don’t you love this place?”

I looked around; on the wall were old photos of New York surrounded by fake ivy. Most of the diners were geriatric. Was this where millionaires usually hung out?

When we were finished, the millionaire announced that this (my coffee) was “on her.” While we waited for her change, she asked me where I lived.

“Brooklyn,” I said.

“Oh, Brooklyn. I love Brooklyn!” she cooed. Her dazzling smile revealed white teeth, and her platinum blonde hair hung to her shoulders; these bright features stood out against her all-black outfit: long-sleeves, jeans, tall boots. Delicate crow’s-feet painted the corners of her eyes. Looking at her, you wouldn’t know she was the daughter of socialites, some of the last of their kind, an American aristocracy of a previous era that we may never return to—she wore no pearls, no diamonds, no visible expensive labels, and she held herself in a relaxed posture rather than a regal or snobbish form. Nevertheless, it wasn’t too difficult to imagine that she probably had not been to Brooklyn more than a handful of times during her forty-eight years.

And then she went back to her Upper East Side abode, and I went back to my shabby shared apartment in Bed-Stuy, heavy with disappointment. I had not found any new material for my story, and in fact, I feared there was not much more material to be had. It seemed I had met this millionaire during the less interesting part of her life—the sober, do-good years, as opposed to the eighties, when she, Cornelia Guest, was named “Deb of the Decade” by Life magazine, which photographed the nineteen-year-old floating topless in the pool at her family estate, accompanied by her forty-three-year-old suitor, a handsome and wealthy real estate manager.

I stumbled upon Cornelia one night in December 2011, when I was desperate for a story. I was coming off the high of writing about Occupy Wall Street for The Nation, as well as publishing an essay in Killing the Buddha about the movement that several people told me had brought them to tears. I was feeling pretty good about where writing could take me, and everything seemed wide open—now was my chance to move ahead!

Thus, it had become my prerogative to write for The New Yorker, the holy grail for any writer, and a publication I had grown up idolizing as the highest form of journalism.

A staff writer at the magazine, whom I had been chasing with questions about how to break in, told me the best entrée was “Talk of the Town,” the short, fluffy pieces that run near the front of each New Yorker edition.

“Talk” pieces are typically about quirky New York City happenings and individuals (Lauren Collins on Manhattan’s Wifi detective), or mini-profiles of famous and powerful people, often in very cozy situations with the journalist (Jane Mayer power-walking with Nancy Pelosi along the Potomac River). They are written in a distinctive, perfunctory, flippant tone, which belies the difficulty in scoring such assignments. Somehow, I thought I had a shot.

Sniffling through my scarf at home one afternoon, struggling with a cold, I sorted through my inbox, and opened an e-mail from the 92Y in Tribeca. There was a panel discussion that night on the “guerilla marketing tactics of PETA,” the animal rights organization known for undercover camera spy tactics, cheeky advertising campaigns, and outlandish publicity stunts that sometimes get people arrested. It sounded interesting, if not quite as interesting as social revolution, economic inequality and police brutality—my most recent story topics. Nevertheless, I sent a brief note to The New Yorker’s Talk editor and headed off to Tribeca.

The next day, I got an unlikely reply from the editor: sure, she would look at a draft. I grabbed my tape recorder and feverishly began transcribing the previous night’s discussion. I had not spoken a word to anyone at the event—had instead sipped tea and observed the discussion through my cold haze—but still, I felt that it could work out. A piece in The New Yorker would take me someplace, perhaps to a job, perhaps just out of this crappy apartment, this hand-to-mouth existence, this perpetual fear that I would never have any stability.

*   *   *

“Thanks to Cornelia Guest, dozens of homeless people will keep warm in fur coats this winter, and several dogs will enjoy the health benefits of castration.”

That was my lead in the draft I sent to the Talk editor. The panel had been convened because of an upcoming billboard campaign, which featured Cornelia posing naked with her long, blonde extensions draped over the parts of her body that could not be publicly displayed—the famous “Rather Go Naked Than Wear Fur” PETA campaign, launched in the nineties.

It wasn’t until after the PETA panel that I learned who Cornelia was. Far more than an animal rights activist, she was the daughter of “lady-who-lunches” fashion icon CZ Guest and Winston Frederick Churchill Guest, a steel fortune heir and polo champion (and the godson, second cousin, and namesake of the former British prime minister.)  CZ and Winston were married on Ernest Hemingway’s ranch in Cuba; the writer was their best man.

CZ’s death in 2003, after illness from breast cancer, had prompted Cornelia to learn more about “health issues.” This research led her to veganism, and eventually Cornelia became passionate about fighting the cruelty involved in the meat and fur industries.

A few weeks before the panel, at Cornelia’s birthday lunch, she had handed PETA all her furs to donate to the homeless. (This statement was not popular with many people in Cornelia’s circle; some of those furs very likely belonged to her mother, a fashion icon at a time when fur was synonymous with status and good taste.) Cornelia had done the Rather Go Naked Than Wear Fur ad, she said during the panel discussion, as a way to “get people talking,” and it had worked: some had been furious at her, alarmed that she would use her naked body to condemn fur, a sacrament of the luxury class; but others had become interested, and were beginning to ask Cornelia about her vegetarian lifestyle.

“People want to know what quinoa is. They say, ‘Kwan-waa? What is that you’re eating?’” piped Cornelia on stage. Her voice was chipper and she spoke quickly.

Cornelia announced that she had recently taken to reprimanding men she saw walking un-neutered dogs in Central Park, explaining that castration greatly reduces risk for cancer.

“One guy said, ‘Well, I don’t wanna take his manhood away,’ and he left in a huff,” Cornelia said. “But a few days later he came back and said, ‘You’re right, I wanna keep my dog for a long time and I told my friends.’ So, it works—if you educate people, and one person tells his friends and so on.”

The piece was “nicely put together,” the editor told me, but still—it wasn’t enough. There needed to be “something from the green room” to make it juicier. This didn’t come as much of a shock to me; it was a blind pitch and I hardly even knew who Cornelia Guest was at that time. But now that I knew the editor was interested in her, I was determined, so I got in touch with Cornelia’s publicist, who was more than happy to set me up to meet the activist socialite for a lunch date.

The idea of having lunch with Cornelia recalled days of my youth spent reading glossies in which the journalist describes dining with a celebrity at a fancy restaurant. The darling actress/socialite/singer shows up wearing dark sunglasses, and says something that makes her sound very normal, like how difficult it was to find parking, or that this place has the greatest French fries. The journalist then describes everything the starlet is wearing and what she orders, which she of course “devours with gusto,” despite being thin as a rail.

Suddenly it occurred to me that someone would need to pay for this meal. Someone…meaning me? The freelance writer with $42,000 in student loan debt, wearing socks with holes in them? The writer who barely ever took herself out to lunch, much less some wealthy lady who probably did coke off Andy Warhol’s forearm when she should have been going to college? I panicked at the idea of having to pick up a $300 lunch bill and wrote to Cornelia’s publicist to “clarify” the terms of the meeting. Alas, we would not be ladies who lunch. Instead, we would be ladies having black coffee and green tea, at—per Cornelia’s suggestion—the lowbrow Three Guys Diner on Madison.

And thus I had my first experience hanging out with a millionaire. And not only was the diner where we met kind of tacky, the conversation turned out to be rather droll. Cornelia mentioned nothing about her wild past, or her parents’ dinner parties with Truman Capote and Nancy Reagan. Rather, she named each of her eight dogs, spoke about how much New Yorkers loved her vegan cookies, and promised that her forthcoming cruelty-free handbags would be super, super cute.

After our meeting there, I gave up—Cornelia had no dirt to give me! It wasn’t that I didn’t like her; she was quite pleasant, friendly, and passionate about animal welfare. In other words, Cornelia Guest was boring. Nobody wants to know about another do-gooder celebrity. What was I supposed to do to make this into a Talk piece if my subject wasn’t having any weird interactions that I could use to make her look overly snobby or boozy or otherwise entertaining in print? I couldn’t think of anything, so I moved on, and shifted my focus back to Occupy Wall Street, which was flailing and suffering from intense policing, but nevertheless still a story worth following. I was disappointed in myself for having put something I cared about on hold to pursue a story even I wouldn’t want to read.

And that was the end of my time hanging out with a millionaire—or so I thought.

*   *   *

Here’s what you need to know about publicists: if you tell them that you might be writing about their client for a magazine like The New Yorker, they will never, ever, let you off the hook. They will do everything possible to get said article published. If you are good at digging your nails into someone and keeping them fixed there, tightly, then you should become a publicist.

Cornelia’s publicist contacted me repeatedly until finally I consented to another attempt. This time, the piece would focus on Cornelia’s forthcoming book, Simple Pleasures, a manual for “entertaining with style”—otherwise known as a recipe collection supplemented by anecdotes about being a good hostess and cute stories about the estate in which the Guests raised Cornelia. Even then, I suspected the story wouldn’t fly, but I had to at least give it another go; the lure of seeing my byline emblazoned in The New Yorker’s namesake font was enough to draw me back to the Upper East Side one last time.

Months, and many e-mails with Cornelia’s publicist later, in the spring of 2012, I was having trouble getting dressed. This dress was too short, and that one had stains on it. These slacks would work, but they had to be worn with heels, and I couldn’t fathom taking the long journey on the G train to the L to the 6 uptown and then three avenues on foot, all while wearing heels.  Before I walked out the door, I sent an apologetic e-mail to the people in my writing workshop—I would not be at our meeting that evening, though I wished (really, truly wished) that I could attend. On the subway, I closed my eyes and imagined how the other writers would be just then convening, sitting on pillows around a bowl of popcorn, clutching printed pages diligently marked with their careful edits.

An hour later, I was in the Upper East Side apartment of John Demsey, the CEO of Mac Cosmetics, who was hosting a celebration for the publication of Cornelia’s new book. Shifting uncomfortably in my heels, with a flute of Champagne in one hand and a small Moleskine notebook and pen clasped in the other, I worried that one of the guests was currently frowning in horror at the large tattoo on my shoulder. The outfit I had finally decided on had included a blazer, but the long commute plus the heat generated by the crowd in Demsey’s apartment required that I shed a layer.

So there I stood, talking to no one, smiling at the pearl-stringed-throats surrounding me, and getting tipsy too quickly. I had asked someone at the door for Cornelia’s publicist, and was pointed toward a woman about the same age as me. Now, I scanned the room looking for her.

Placing my empty flute on a tray held by a waiter, I approached the publicist. She welcomed me warmly, and steered me toward the lady of the hour, who greeted me with a kiss on the cheek. Cornelia looked dashing. She was in a short, navy blue dress that accentuated her ample cleavage, plus stockings and pumps; her hair was down and swept over her shoulders, and her make-up was perfectly applied (by the CEO of Mac Cosmetics himself, I wondered?)

“How long did the book take you?” I asked Cornelia, pen poised over my open Moleskine. Quotes, give me good quotes! “What was the most challenging part of putting it together?”

The socialite opened her lovely, painted lips to reply to my questions, and just as I caught a glimpse of those shiny white teeth, the fashion designer Carolina Herrera entered the apartment, and Cornelia ducked away from me and into Herrera’s arms, from whence ensued a cacophony of polite cooing and kissing and complimenting.

I moved away and stood strategically in a corner near where Cornelia continued to greet the influx of guests who arrived on Herrera’s tail, and where I was also well-placed to pinch from the plates of hors d’oeuvres, all prepared with recipes from Simple Pleasures—polenta cakes with roasted vegetables; some savory seitan thing. After a while, I winked at Cornelia’s publicist, who looked like she was about to pounce on me, and hastily made my exit before she could do so. On the train, I contemplated showing up late to my writing workshop and catching the last few minutes, but my feet hurt too much, so I went home.

*   *   *

A few days later, I went back uptown to see my millionaire again—this time, to Bloomingdale’s. While I awaited Cornelia’s arrival, I watched the New York Gay Men’s Chorus belt out a few tunes in the middle of the ladies’ handbags department.

The Bloomingdale’s staff set up a table with Cornelia’s handbags. They looked pretty nice, and the price tags actually weren’t too bad—under $300. Shortly before six, Cornelia showed up with her publicist and another assistant. They placed a stack of books on a side table, and it was show time. Cornelia took a stance behind the table and adjusted the bag display. She wore a knee-length striped black-and-white dress under a small black jacket, black shoes with high heels that revealed her painted toenails, and droopy, sparkly earrings, with her blonde hair in a neat low ponytail. I was again wearing my uncomfortable heels. Perhaps if I decide to resume attempting to write about rich people in the fashion world, I will find out what kinds of shoes look decent without killing your feet.

From my second Talk draft: “She tweeted to her 1,111 followers that she had arrived at her book-signing. Then her eyes followed a small white dog being led on a leash by a woman wearing a trim black dress. ‘Oh, I should’ve brought my little dog,’ said Guest wistfully, referring to Olive, the West Highland Terrier who lives with her in her apartment some blocks uptown from Bloomingdale’s. Guest’s seven other dogs dwell at Templeton, the estate in Old Westbury, Long Island, she inherited from her parents…”

While Cornelia tweeted and dog-ogled, friends began arriving to congratulate her on the handbag launch. One after another, tall, handsome European men wearing dapper suits with pocket scarves kissed, hugged and screeched compliments at Cornelia. I hovered nearby and took notes, occasionally zeroing in on the table when the conversations grew quiet, feigning interest in the hot-pink lining on the bags so I could get the scoop.

Dennis Dunn, Bloomingdale’s director of visual, approached the table. He hugged Cornelia warmly and asked, “Where’s the cookies?” He was referring to Cornelia’s vegan chocolate-chip cookies, which she produces through her mostly-vegan catering company and sells in stores around Manhattan.

I was starting to get bored, and thinking about sitting down so my aching feet could have a rest, when a heavyset man in a plaid blazer walked up to Guest and pulled out a copy of a 1983 issue of Life magazine—the one that featured nineteen-year-old Guest floating in her parents’ pool.

“I remember seeing you seven years ago at the local Bryant and Cooper Steak House,” the man, Danny Frank, told Cornelia. (Guest had been a vegetarian for six years at this point.) This was my moment—finally, something interesting was happening! Would Cornelia get embarrassed? Would her friends poke fun at her? Would potential customers be scandalized that she had been spotted at a steakhouse?

But no—the millionaire was deadpan. She grabbed a marker and signed the magazine, then ushered Frank toward the stack of books, encouraging him to buy one. He did, which brought her book sales for the day to seven, and my journalistic successes of the day to zero. I spent another half-hour there, sitting on the steps behind the table where Cornelia was signing books and selling handbags, trying to ignore my stinging heels.

*   *   *

I wrote the thing and sent it in. When the rejection e-mail came, I removed the busted windowpane that led to a dilapidated patio near the little kitchen-living room where I did my writing. I climbed out the open window onto the patio and rolled a cigarette.

As I smoked, looking out over the low rooftops of Bed-Stuy, I swore that I would never again pursue a story for the sake of glitz and glamour—for the sake of getting published in a fancy magazine—unless I was authentically interested in the subject matter. Cornelia Guest, it turned out, is a nice person, doing pretty nice things with her life, and doing them pretty well—a millionaire, but someone who kind of shrugs at the whole thing and focuses on what she enjoys: cooking healthy food, seeing her fashionable friends, spending time with her critters. No scandalous affairs with Wall Street tycoons or, conversely, her chauffeur; no throwing cell phones in frustration at her assistants; no membership in a weird religious cult; no secret addictions to drugs or even hamburgers. (At least not that we know of.) Really, what was there to grab onto and satirize in print?

I guess what it all comes down to is that millionaires, it turns out, aren’t inherently interesting just because they’re millionaires. Or maybe—and perhaps Cornelia would agree with me here—what it all comes down to is that I just really need a new pair of heels.

*   *   *

Rachel Signer is a Brooklyn-based writer. Her essays, journalism, fiction and memoir have appeared in The Nation, the n+1 Occupy! gazettes, Construction magazine, The Brooklyn Rail, and elsewhere.

Sophie Butcher is a freelance writer, photojournalist, illustrator and designer who lives in Brooklyn. She has exhibited work in The New York Public Library and The Museum of the City of New York, among other places. She is currently working in the photo department at TIME Magazine.