Jess
Ianswered a photoless Holidates ad.
Benjamin H., 29
New York, NY, & Martha’s Vineyard, MA
Redacted. I do well.
Hot Black Coffee, Rodin, Classical Music, NYC streets after 2 a.m.
Holidate needed for Halloween Weekend in Martha’s Vineyard. Travel costs and compensation provided.
Mistake.
I knew it. As I packed my things, I knew it. Lugging my suitcase up the bus steps, I still knew it. And standing on the curb at LaGuardia Airport, I was totally and fully aware that selling myself as date extraordinaire to some faceless guy for Halloween weekend was a terrible idea, but I needed the money and I needed it quickly.
Earlier in the month, I took a deep dive into my current artistic endeavor and called in sick to work for a couple of days, which was usually not an issue. I’d let my side gigs slide a few times before and was always able to make ends meet, but this month, no one had extra shifts or overtime for me. And I absolutely needed to make rent by November first because losing my apartment meant losing my darkroom or studio. Nowhere to work on my photography felt like the end of the world. Homeless I could handle. I’d been there, done that. But no darkroom? Not an option. Not at all.
Enter the Holidates app, my route to easy money. A couple months ago, my best friend, Catherine, sent me an article about the founder. Catherine was always sending me stuff about female entrepreneurs because she was trying to convince me to go into business with her. She’d say things like, “All we need is one great idea, Jess.One great idea and you can stop doing every job on the planet.”
Basically,Catherine hated that my art took up all my free time, and the only way she could see to get around that issue was to spend my work time with me. Her dream of us working together was half joking daydream and half reality. But either way, that was why she sent me the article about the Holidates app; it was supposed to inspire me to come up with the next great female founded and focused business, but instead all I saw was another possible side gig. Most of the dates on the app were about convenience or actual dating but sometimes people offered compensation for a date.
The article was also very clear that according to the Holidates app terms of service, under no circumstances did it facilitate sexual escort services. So it sounded like a win-win to me—get paid to get dressed up and go to a party or a dinner and socialize. No strings attached. No deep moral quandaries. Sure, you had to talk up some guy who may or may not deserve it, but that was a tiny concession for a big payday. I told myself that as long as Benny boy wasn’t a psycho killer, being his fake girlfriend for a hot minute wouldn’t hurt anyone. One weekend of easy work for a cool 2k was certainly worth it.
And so, there I was, standing on the curb, scanning the crowd for Benjamin H., age twenty-nine, who liked Rodin and told me in a text message to look for a man in a navy-blue wool sweater with leather patches on the elbows. Not sure what kind of twenty-nine-year-old liked elbow-patched sweaters, I responded by texting,Will you be smoking a corncob pipe too?He answered curtly,No.Leaving me with the impression that Benjamin H. was either a prematurely professorial curmudgeon, a run-of-the-mill douche canoe or a nerdy chubby guy with social anxiety. I was certain that I could handle any of the above, until I spotted him.
Tall and lithe, he was standing by the door glancing repeatedly at his watch and shaking his head in a way that made his perfectly coiffed mess of wavy hair ripple. His brow was furrowed and his edgy jaw staunchly clenched. His knee bounced impatiently and maybe if I didn’t already know who he was, I would have been able to look past his obvious anxiety and irritation, and treasure how richly handsome he was, but I did know him, so I told my brain to disregard all his appealing pretty man.
Benjamin H. was none other than Ben Hoffman, youngest man to ever win the National Medal of the Arts. He was a painter. No, he was the painter of my generation. He was also a shitty person. A stuck-up, elitist ninny who openly dissed art forms that occurred outside the tradition of classical art. He didn’t appreciate indigenous crafts or performance art, and he had a real hard-on for putting down photography and other digitally manipulated or technology-based artworks. I kind of hated him.
Well, not really. As a person, I tried not to hate people I didn’t really know. And while I’d been in the same room as Ben a couple of times, serving as a cater waiter while he hobnobbed within the art world, I didn’t actually know the guy.
So, I pushed on, took a deep breath through my nose, huffed a sigh out my mouth, bent my head down, and made a beeline in his direction, dragging my three-wheeled suitcase along behind me.
When I got close enough for him to hear me, I jutted my hand out and said, “Benjamin?”
He didn’t acknowledge my offer of a greeting. Instead, he perused my appearance and asked, “Is this what you’re wearing?”
Instinctually, I glanced down at my outfit. I was in a pair of black leggings, an oversized I heart NY sweatshirt and I had my hair pulled back in a ponytail. It wasn’t a particularly sophisticated look, but it was absolutely the kind of outfit most women wore when traveling. I couldn’t help feeling defensive, but I learned a long time ago that there was no use arguing with a man like Ben, so I shrugged and said, “Yes, I prefer comfort when I travel.”
“My mother is picking us up at the airport,” he said, his tone condescending. “I would like you to make a good impression.”
I kept a slight smile plastered to my face as I told myself that this was just a job and a lot of jobs required uniforms and working for assholes. I had handled both in my past. I needed this money, so it was best to just be pleasant and acquiesce.
“Well, then,” I said, keeping my tone even. “I will be happy to change, sir.”
My lack of annoyance and deferment to him as my boss seemed to please him. His brow softened, and he didn’t smile but he stopped frowning before pointing to my luggage. “Also, we will need to manage that atrocity, and if you were truly my girlfriend, why would your suitcase be broken?”
Not capable of buying a new bag and not wanting him to deduct from my earnings by spending his money on a new bag for me, I suggested an alternative. “Perhaps it broke en route. A traveling hassle could distract from the need for too many revealing details. I am honestly not your girlfriend so something outside of our relationship to discuss with your mother would be a welcome diversion, wouldn’t it?”
His brow tightened again before he said, “Yes, fine.”
Then he turned and headed for the check-in desk without saying anything else.
We were in first class. I, Jessica Darling, the girl who grew up bouncing from one ugly foster situation to another until she wound up homeless but managed to beat the odds and work hard enough to just get by, the girl who had only been on a plane one other time in her entire life—when my bestie Catherine gave me a trip to Puerto Rico for my birthday two years ago—I was in first class. And it was definitely weird. I felt like a fraud, like people were staring at me, wondering, what is she doing here? I shifted nervously in my seat until the stewardess leaned in, holding out a cocktail napkin, and asked, “Can I get you a glass of champagne or a mimosa before takeoff, ma’am?”
“Uhhh…” I stammered.Was it free?I glanced in Ben’s direction. He hadn’t said anything to me other than reminding me to change my clothes as we passed the ladies’ room on the way to the gate. He shrugged, giving me a total lack of consideration, which I interpreted as consent. Figuring you only live once, I nodded yes as I said, “A mimosa, please.”