My Secret Life as a Personal Assistant to 'America’s Most Eligible Man'

He was the former star of an uber-popular reality dating show. I was a feminist lesbian 19-year-old—a.k.a. the least likely person on Earth to become his coach in life and love.

Illustrations by Abelle Hayford | Story edited by Naomi Zeveloff

The first time I met Ben, I had no idea who he was. This is probably why he hired me to be his executive assistant, although he told me it was because I had “really nailed” the cover letter.

“A good cover letter opens doors. Are you considering a career in business?” he asked me at my interview, which we conducted over French toast and coffee at a little cafe on Avenue A and East 6th Street. I was grateful for the free meal. I was a sophomore at New York University, and I’d applied to the job less out of an interest in being an executive assistant than out of despair over my constantly overdrawn checking account.

“Oh, no, definitely not business,” I said, with the casual confidence of someone too young to know to lie during job interviews. “I’m going to be a poet.”

Ben, whose name I have changed here to protect his privacy, was 15 years my senior, but he kindly refrained from pointing out that I was getting a very expensive degree from a very prestigious school in a field that was almost guaranteed to make me no money. “Poetry. Huh. That’s … great. Actually, I’m a bit of a creative myself.”

The server arrived with our coffee. Impressed by his full sleeve tattoos, I tried to make eye contact, but he was entirely focused on Ben. In the East Village, unironic enthusiasm was against the neighborhood code of conduct, but apparently Ben was worth breaking the rules for. “Hey, man, loved your show!”

Ben chuckled in a very modest and very practiced manner. “Oh, thanks, it’s always nice to meet a fan.”

“Yeah, man, of course! Don’t give up!”

Give up on what? I had been in New York City for a year, and it seemed like every day something strange and wonderful happened. Ben leaned over the table toward me conspiratorially.

“You may have noticed I look a little familiar … ”

I hadn’t. He looked completely like what he was: a mid-30s analyst at a prestigious financial firm. He was tall, dark and generically handsome, and he wore the same weekend uniform as all of the other similarly situated white dudes in the East Village: dark washed denim, designer T-shirts, and brown leather loafers.

“Now that you mention it, you do look familiar,” I lied, already learning valuable business lessons.

“Yes, well, if you haven’t seen the show, you’ve probably seen me in magazines.” He told me that he had recently starred in a reality dating television show. He was, as dozens of magazine covers and the show itself put it, “America’s Most Eligible Man.” He had starred on one of the show’s first seasons, and in the two years since filming it he had managed to springboard his way into the glamorous world of D-list New York celebrity. Now, he was the spokesperson for a popular dating website and dreamed of a career in television.

“But, for now, I’m keeping my day job!” he laughed in that wonderfully rehearsed way. His head thrown back and mouth wide open, I could see his perfect teeth. They were bleached a tasteful, not-quite-blinding white. Probably any other woman in the world would have been charmed.

“Cool,” I said, my mouth full of syrup and sugary bread. “That sounds like a good plan.”

He leaned back, and I understood that I was being evaluated. Not a fan of his show. Not impressed by his fame. Not, by any stretch, the sort of young coed you might make your assistant and then have sex with. I had a faux-hawk and several facial piercings, and I’d mentioned my live-in girlfriend within minutes of sitting down. I was a self-described militant feminist dyke, and I was about to spend the next two months of my life sorting through the metaphoric and literal dirty laundry of the city’s most famous bachelor.

Through the power of my cover letter and the novelty of my complete lack of interest in both men in general and the man I would be working for himself, Ben offered me the job before our meal was over. My starting salary was $15 an hour, cash. It was a lot for a college job in 2005, and it solved my immediate financial strain. I was thrilled and determined to make a good first impression. Which is why I didn’t flinch when, on my first day of work, he led me into his closet.

He lived in a trendy building in Alphabet City, in a large loft-style apartment with four roommates. This was strange, because while New York has always been expensive, the neighborhood was still comparatively cheap at the time. I had imagined that being professionally single would be more lucrative.

The first assignment he gave me was to reorganize his closet, including going to Bed Bath & Beyond, buying the necessary parts, and installing shelving. Perhaps my lesbianism had given him the impression that I would be good with tools, but I am not handy. I have consistently found ways to shirk manual labor throughout my life, and in this way, I was not so different than Ben. A good smile and a charming laugh can get you on a reality TV show if you’re an overeducated wink. He thought that we could relate to each other based on our shared sexual attraction to women, but I did not at all relate to Ben’s romantic pursuits.

Inside the shoebox were hundreds of paper napkins, business cards, and scraps of paper with women’s names and numbers written on them. My task was to input this data into his Microsoft Outlook contacts, in a folder titled “Black Book.” This in and of itself was strange enough, but it got worse: On each scrap, he had also written some kind of evaluation of the woman, which was supposed to go in the contact’s notes.

Tina, 42, has fake tits but they feel real.

Marie, 31, has husband but he travels for work.

Brenda, 24, amazing blowjobs.

It went on and on like this, all the way to the bottom of the box. After Ben left the room, I tried taking them all out and separating them into piles based on their medium: napkins in one pile, business cards in another, torn sheets of paper in the last. (They were mostly sheets of yellow legal paper. Did he have a particular thing for paralegals?) But I’d only made it halfway through when the piles got too big and tipped over. I threw them all back in the box, and began selecting them at random, embarrassed both for these anonymous women and for myself. But there was something exciting about reading the notes, as one salacious comment seemed to top the next.

Most people with an ethical compass — certainly one as strong as I believed mine to be — would have quit the job immediately. But I didn’t. In fact, I had accepted his instructions without comment, except to ask for his Outlook password. I spent the rest of the afternoon there, cross-legged in his office chair, squinting at each scrap as the light faded, then typing his little misogynistic bons mots word for word. It didn’t occur to me to get up and turn on the lights. That would have slowed me down, and as long as I kept my pace up, I didn’t have the time to dwell on the pit of horror in my stomach I was doing my very best to ignore.

I have always been a people pleaser, a habit I have mostly corrected now that I am in my mid-30s, but which I was still struggling with back then. I didn’t want to upset anyone at all, ever, and that extended to this creepy quasi-famous single man. I spent days, maybe even weeks, creating his digital black book. I was taking a class on Greek mythology at the time, and I felt like a modern-day Sisyphus, adding contact after contact but never reaching the bottom of the box.

In the mornings when I arrived, Ben would casually hand me a new stack of women’s numbers and evaluations. He did this without any overt display of emotion, but in hindsight, I can remember a certain twinkle in his eyes. He seemed to want me to react, and while I tried my best not to, I have never had a poker face. My cheeks were permanently hot those weeks that I worked on his black book. We both knew that I was embarrassed, and we both knew that I needed the money. Had I reacted more obviously, more judgmentally, he might have had to judge himself too, but he had me — a fellow lover of women — there to let him off the hook, an investment to prove his innocence.

My guilt extended to the women whose names I was logging. When Tina or Marie, or whomever last night’s conquest had been, spent the next day checking her phone, first hopefully, then increasingly dejectedly, waiting for a follow-up text, I was the one holding their phone numbers in my hands, out of his reach until he got bored and went searching through his catalog to find one of them worthy of a second night. They knew the charming figure they had seen on TV, America’s most desirable man, but I knew the actual man, and had I been a bit braver, I would have called them myself, told them that sometimes desire is akin to disaster.

I didn’t tell my girlfriend about the black book and my complicity in it. Getting home from a session of logging names, I would feign total boredom with my work. “Oh, nothing much today, just organized some files.” I made less money in my other side gig as an LGBT peer educator at NYU, teaching students how be to good allies to the queer community, but I was far prouder of that job. I would stand on a stage and deliver my lessons, relishing the attention. Ben and I had plenty of things in common, and a love of being the star of the show was one of them.

“I want everyone here to take a moment and think, really think, about why it is you put on makeup in the morning, or, for you gentlemen, why it is you keep your hair short. Who would you be without those things? Gender isn’t absolute, and too often it’s a prison we build for ourselves.”

My girlfriend and I had met because she had attended one of these presentations and fallen for my complete devotion to the cause. How could I ruin her view of me by admitting what I did on the days I spent with Ben?

What I did tell her about were the things I learned from his emails; by that point I was snooping through his Outlook account on a regular basis. What I found made him much more relatable, allowing me to forgive him to a degree. Like the fact that he had really believed he might find the love of his life on network television, and he was still heartbroken that it hadn’t worked out. The producers had told him he would have the chance to meet a dozen carefully selected women, and that he would absolutely be walking away with a wife. I rented his season of the show on DVD, and my girlfriend and I binge-watched it together one night on our tiny dorm room TV. We watched him drink champagne in a hot tub, flanked by blondes laughing at his every word. We watched him profess to the cameras that he felt a “real connection” with two of those bubbly blonde women, then agonize over which one he ought to propose to. We, two brunette lesbians, watched in amazement and disbelief.

“How could anyone think this is a legitimate way to fall in love?” I said, in between messy mouthfuls of popcorn. We had melted extra butter to pour on top. There were many reasons I was happy to not be a straight woman, and the freedom to be a size 12 was near the top of the list.

“If you had been seeing 10 other women when we met, I would have never let you in my bed,” my girlfriend said. I shoveled more popcorn in my mouth and feigned deepened interest in the show. What my girlfriend didn’t know was that up until our third night together, I had been flirting with and occasionally sleeping with two other members of the LGBT peer educator group.

“Yeah, that would have been a nonstarter,” I lied. “Did I tell you about his life coach?”

He had a life coach he had sent long, sad emails to about his failure to become more famous or find a wife, and she would reply reminding him to “keep the color of his parachute in mind,” a self-helpy encouragement to stay true to himself. The more time we spent together and the more of his emails I read, constantly looking over my shoulder to make sure he didn’t walk in and catch me, the more I recognized something of myself in him. I didn’t relate to his quest for fame, or his horrible treatment of women, but I related to his sadness. He was deeply insecure and vulnerable, and he was trying to fuck his way to self-esteem. Years later, when I was roughly Ben’s age, I did the exact same thing. Well, almost: I never kept a shoebox.

Ben left me alone while I worked, but he made it a custom to show up around midday and buy me lunch. I don’t remember what we talked about, not really, although I do have a vivid memory of a winter afternoon spent in his apartment eating burgers from the pub on the corner. It had snowed, and everything outside was cloudy and white, but it was cozy in the loft. It’s a warm memory, a nice one. Ben seemed genuinely interested in my studies and career plans. He gave me advice that has been useful ever since; it was good, he said, that I was working during college, and I should keep adding things to my résumé. I didn’t realize it at the time, but the executive assistant title he’d given me was a real gift that helped me land a series of good internships and in turn led me to my first full-time job.

On that particular day, Ben was overflowing with enthusiasm about how well things were going at work.

“That’s so great! I’m glad things are going so well!” I chirped back at him. I knew from his emails that work, in fact, was not going so well for him. I had started to pity him, and I genuinely wanted to cheer him up.

“Yeah, you know, you should really reconsider this poetry thing,” he said. “I think you’d be great at business! Just think, by the time you’re my age you could be just like me.”

“That’s a great point, man! I’ll think about it.”

I did think about it on the taxi ride home. (Ben gave me money for the fare.) What was I doing with my life? I liked writing poems, sure, but even my professor and mentor had warned me that he’d made less than $100 off of his last book. But by the time I got back to the dorm, I had moved on from delving too deeply into my life plans. I was young, and all I needed to know was that later that night, my friends and I were going dancing, and I had enough money to bring a bottle of vodka to our pregame party.

What was I to Ben? Some sort of cross between a personal assistant, a maid, a life coach, and a fast and judgment-free transcriptionist. I say life coach because I eventually worked up the courage to tell Ben what I thought about the shoebox. It was during one of our lunches; he was bemoaning the lack of true love in his life. It felt like the hundredth time I had heard the complaint — I had read practically every email the man ever sent or received by then — but it was probably the first time he told me face to face. His chin had a smear of barbecue sauce on it, which on him was somehow charming, even to me.

Somehow, along the way when I wasn’t looking, I had fallen for his charms. Despite everything I knew about him — despite the shoebox of women — he had become a friend.

“You know,” I said, aware that I was crossing a line, a friend but still one on his payroll, “if you really want to get married, the way you’re going about it is silly. Women don’t want to be objectified. You should ditch the black book and just try to be honest with someone.”

He looked at me in a new way. It might sound delusional, but I always felt respected by Ben, and now that respect seemed to turn to reverence. He put his burger down, leaned forward toward me until we were just inches apart. Up close, you could see specks of green in his eyes, and for just a moment I wished he would lean in even closer.

“That’s actually … that’s a good point,” he said. “Thanks for that. I’m going to talk about this with my life coach.”

I snapped out of my reverie. How was it possible that his life coach, or, really, anyone else in the world, had never suggested this to him? He truly seemed to be taking it as brand-new information. Women deserve respect: Not exactly a radical statement, but radical enough, apparently, for a mid-30s dude-bro.

I didn’t work for Ben much longer after that. I didn’t quit in a moral outrage; by the time I left I would have told you I liked him. But the strangeness of the job had worn on me, as had his emotional neediness. He required a friend, a real friend, one who didn’t care that he had been on TV, and one who wasn’t hired help. I parlayed my now fleshed out résumé into an internship at a political nonprofit and gave my notice, which he accepted gracefully.

I never saw him again, although a friend who waited tables in the Village reported that he frequently came in with his friends and leered at her and her fellow pretty coworkers. I sighed and shrugged when she told me. I had naively assumed that my life-shattering truth bomb would have changed his behavior, but of course, it takes more than a 19-year-old lesbian to eradicate toxic masculinity from the planet, let alone one guy.

I am now the same age Ben was when he hired me. I think of him every time I write a cover letter, and, of course, whenever the now wildly popular dating franchise he helped launch comes up. Those excellent cover letters have indeed opened many doors, eventually leading me into a career in corporate real estate, a turn of events I have to admit he was right to encourage. It sustained me while I avoided writing, and then supported me while I went back to school to turn writing and teaching into a career. My brief employment by a D-list celebrity has also made for a good story to tell at parties.

And yet, the story of me and the World’s Most Eligible Man isn’t just a joke. When I see the ridiculous dating franchise, it is with fondness that I remember him, flaws and foibles aside. You could interpret his assigning me the shoebox as an aggressive and blundering act, a way to impose his power over a vulnerable young woman, but that’s not how it was. It wasn’t hostile, it was sad, desperate. A man-child with no real intimacy in his life but crumpled napkins and the memories of sexual conquests. I still relate to the longing of it.

I was slightly horrified when I recently discovered an old file in my Google Docs, a list from my senior year of college. I had long since cheated on and been dumped by the girlfriend I’d been with while working for Ben, and I had, like him, been fucking my way to self-esteem. “Women I am interested in right now” is the title of the file, and while I don’t discuss boobs or oral sex prowess, it’s still a list of conquests with corresponding notes, not so unlike Ben’s black book. Didi, old but charming. Carolyn, she’ll need convincing. Carrie, best orgasms. I never forced anyone else to be a party to my callousness, but I was guilty of it just the same.

Fifteen years later, Ben seems to have entirely given up on his quest for fame. He has zero online presence, and while I can’t know for sure, I like to imagine that soon after we parted ways he burned the shoebox, found a nice woman his own age, and settled down.

I’ve yet to find a great love and settle down, and I’ve become a reluctant fan of reality dating shows. It’s ludicrous, a farcical distillation of our cultural preoccupations with love and romance and marriage. It sounds crazy, on its face: Who would expect to find true love in six weeks while being filmed 24/7 and drinking superhuman amounts of chardonnay? But then, who expects to find love anywhere, in any moment? And who hasn’t, at some point, wished they were famous? On days when the panic sets in — I am not young anymore, I am running out of time, I want a family, everyone else has one, why not me — it is comforting to watch other people behave extremely foolishly out of the same panic.

On one of my last nights working for Ben, he left for a date and his roommates offered me a glass of wine. They were curious about him, and therefore curious about me by proxy.

“So, like, what does he even have you doing for him?” his female roommate asked. “He’s kind of weird, no?”

Ordinarily I am a ready and eager gossip, but I am also loyal to my friends. “He’s not that weird,” I said. “He’s just figuring some things out.”

I finished my wine, put on my coat, and walked out into the strange and wonderful city where everything and everyone was still possible.

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Joanna Greenberg is a writer, editor and educator based in Southern California. Her essays have appeared in The Los Angeles Review of Books, Hippocampus Magazine, Mud Season Review and elsewhere. She is working on a memoir about finding her biological family through DNA testing.

Naomi Zeveloff is a writer and editor who lives in New York.

Abelle Hayford is a Ghanaian American illustrator, character and color designer. Abelle’s current body of work consists of diverse characters and narratives, good vibes and a lot of pastel colors.

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This post was originally published on June 01, 2020.