Tales of a First Date Dress

by Charlotte Egginton

I found my first date dress at the start of the summer, in the sales rack of the Soho Mango. It cost ten ninety-nine, loose threads on the cinched waist, soft fabric in the cheap way. High neck, cap sleeves, short skirt. It felt like it had already been places, this dress. How does one distinguish a garden-variety dress from a first date dress, you may be thinking. Good question. The perfect first date dress gives only a suggestion of form, an illusion of modesty. As you twirl, the hem lifts, revealing a flash of thigh. Any glimpse of your body must feel like it was taken, not given.

I’m a post-college transplant in this city, a certified outsider, and gone are the days of casual human interaction in shared space. I feel just as lonely in the teeming coffee shop as I do in my fox-hole bedroom; even relationships, it seems, require a referral in this city. And there’s only so many times you can read a Hinge love story pasted on the wall of a subway car before you start to think, who do those two lucky strangers think they are? Who are they to find love, and not me? What better way to launch into my new life than with a summer-long-string of first dates with New York’s finest? Oh no, you may be thinking, this poor idiot.

Oh no, indeed.

Categorization is a natural human response to the unfamiliar. We search for patterns in people and places, trying to understand where we will come to fit into the larger picture. The same is true of dating, at least for me. Some categories of men are more easily identifiable than others. I became familiarized with the finance bro in college, albeit in his earlier stages (as we know, retirement for lacrosse players is also known as ‘working in private equity’). Plus I now live in the thick of a finance-bro area of town. Run-ins are scarily common.

A finance bro called my name just the other day in fact, as I was crossing the street by my apartment. Turns out he and I had gone to college together. He struck up confident conversation with me right there in the road, despite the fact that we’d previously held a strictly instagram-mutuals kind of relationship. Ease with women is typical of the finance bro, a trait shared by both the performative male (mustached, soft-mulleted, tote-bagged, patchwork-tattooed: you know him well) and the tortured artist (pure evil, avoid at all cost).

But reader, my investigations have concluded that we in New York are faced with a new tricky breed, one which I have taken it upon myself to unravel for the greater good of womankind: the Start-Up CEO.

These boys…They’ve just turned twenty-three, whip-smart, stretched thin, bursting with potential. There are people reporting to them and they are learning the art of delegation. They have more money and time than they know what to do with. So they get a penthouse in Hell’s Kitchen with a 360 view of the skyline. A membership to Equinox. They spend every weekend at an EDM concert, surrounded by sweat and life. They ski in the Swiss Alps, and join poker clubs to bet against important men. Women are paying attention to them, and they don’t quite know what to do. They pretend to. They are small men, performing.

Let me set the scene of the particular harrowing ordeal I want to share with you: there I stand on MacDougal street in July, sweating in my first date dress, waiting for my darling CEO. It is a warm evening. He isn’t the first of his kind to take me out on the town, but so far the most creative: a comedy show is truly an inspired first date. None of the ice-breaking has to be done by the couple in question, plus the two-drink minimum never hurt anybody (I’ve concluded that ease with women is decidedly not a defining trait of the Start-Up CEO).

My lover for the night orders a whiskey on the rocks, and for me, a fruity little cocktail. He loves to explain things to me, hang his sweet arm around my shoulders. With his delicate wrists, he looks like a boy trying on his father’s silver Rolex, admiring its sparkle in the low light.

Watches are getting ridiculous these days.

Of course, I’m no better. In male company I often find myself making the most adorable of mistakes, spilling things, losing my way, fumbling words. I can only giggle girlishly, my eyes wide and round-ish. My posture is suddenly perfect.

Both on the comedian’s stage and off: all of us, performing.

The more we drink the more we settle into our own bodies, our honest ways of being. He drops the act and orders a fruity little cocktail of his own. I slouch into his side. We discover how much we actually have in common, both of us being quite nerdy beneath our shells. He reveals his solitude to me gradually, covertly: tired of living by himself, he found his current roommate, a fellow CEO tech bro, at the Equinox. The story feels vaguely familiar, and I tell him so (I’m tipsy, what can I say). He frowns. It’s sweet, I say, correcting myself. My lover seems placated.

I imagine his and his future roomie’s hands brushing for the first time as they reached for the twenty-pounder, looking up into their own face, reflected back. It’s really no wonder they found each other. It must be lonely all the way up there, at the top of the food chain.

The blue night creeps in. We glow. It begins to feel, as it sometimes does a few hours into a first date, like we actually see one another. Like something beautiful is afoot; two familiar people, walking hand in hand in the dark. Love unfurling its green head, blinking its kitten eyes in the space between our shy bodies.

It’s never fully dark in New York.

Before I know it we’re in the lobby of his apartment building. Which I have definitely seen before. I tell him so (I’m drunk now, what can I say), and he’s suddenly suspicious of me. “Must have been with your other boyfriend.” I laugh. So funny! But when he presses the thirteenth button in the elevator, my stomach sinks.

And now it’s too late to run for it. His keys are already in the lock.

We enter an apartment I know. The loafers lined by the door are my final confirmation. My memory is upon me, another night, another boy. Compliments on my first date dress. My lover’s buddy from the Equinox, the other Start-up CEO, is a man I already know, who brought me up to see his God’s view of the city and smoke dreamily out his window.

I’m horrified. Light seeps under the crack in the roommate’s door, I see the shadow of his feet moving, and I all but throw myself into the bedroom of my lover for this night. Who, meanwhile, oblivious to my horror, is back to his pretending: switching on red lights, pouring two glasses of white wine, scrolling for a playlist of sexy music.

And then, just when I’m coming up with a reason to high-tail it out of there, it starts to rain. Splashing, dripping against the tall glass. Lightning cracking far away. I finally understand the purpose of an apartment with big windows, with a big view. To remind us of our microscopy. To show us things that are real. I turn to my lover, who isn’t technically my lover yet. His face, the face of a sweet boy, illuminated by the passing strikes of light.

I’ll ask you not to judge me for what inevitably follows. Just know that the only thing worse than a walk of shame is a walk of shame you’ve done before. Down to the dress.

I already know I won’t be hearing from them, those boys. Whether or not they discover my duplicity. They’re discovering how to be men, the kinds of men who only know how to use. Who can only look onto the next. Who can only see a thing for its potential. It doesn’t quite sit right with them yet, this destruction, but just give them a few more years. They’re fast learners.

As I stumble down the unending avenue, New York heaves its beastly mechanical chest, and we all turn its cogs. Walking up, and up. Breathing our hot hope into the morning steam. Our teeming bodies, headed home.