Why Am I Still Single in New York City?

Catch up on the first six chapters here.

Monday, 9 p.m.

I’m on the phone with Melissa, a matchmaker who found me through a mutual friend. She’s not the first who’s tried to add me to her database after scoping out my LinkedIn and personal socials. Matchmakers love my résumé. And men love my tits. So there’s that.

Melissa’s interview is so thorough, you’d think I were applying for national security clearance. How long was my last relationship? Where do I see my career going? Where have I traveled? Damn, do I at least get TSA PreCheck after this? “You are such a treat!” she says. “How is someone like you still single?” And there it is. Validation served with a cold side of pity.

Look, I get it, how Melissa sees me: Despite the fact that I have advanced degrees, the most supportive friends, and a career I’m killing it in and that I am genuinely happy, there must be something fundamentally wrong with me if I haven’t found my forever person at an age when my grandmother already had four kids.

And I’ll be honest. There was a time in my early 20s when getting engaged felt like the only achievement that mattered, and every year that passed without hitting that milestone made me internalize deeper and deeper shame at my failure. But somewhere down the line, I stopped tying my self-worth to my marital status and redefined my mindset. Do I want to get married? Absolutely. Am I in a rush? No. My person will come when they’re meant to, and in the meantime, how lucky am I to get to fool around, friend-zone, or fuck to my heart’s content?

Anyway, while trying not to sound like an asshole, I let Melissa know that finding men generally isn’t my issue. And I have had some opportunities to settle down over the past decade…but the operative word is “settle.” I’m looking for a very specific puzzle piece, a true partner and best friend, to complement my life. As a child of divorce, I’m hypersensitive to spotting fundamental value differences that signal long-term compatibility issues. And those are more important signals than a résumé, net worth, or abs. I’d rather be happily single than unhappily married (although looking at my bank account, sometimes I wish I hadn’t turned down more than one trust-fund baby). So unless Melissa has someone truly remarkable, I don’t need to be set up.

“I think I have the perfect person for you,” she says. She sends me photos while we’re still on the call. They’re a little blurry, but I’m digging this guy’s well-conditioned shoulder-length hair under his olive beanie. “Winston is wildly successful, very social, a family man, and extroverted. I’ve been waiting to find the right girl to set him up with. He’s the ultimate New York catch.” Okay, fine—why not? Maybe her catch of the day will have potential for my long-term menu.

Saturday, 6 p.m.

I’m from Florida, so I do love a good early-bird special, but a 6 p.m. dinner in NYC might as well be brunch. I’m one glass of red deep waiting for Winston to arrive.

“Zara?” A man approaches my table.

No fucking way. Where is the long, flowing hair? The hinted-at impressive stature? This man is Dr. Phil bald. With my three-inch heels, I tower over him (which, at 5’2”, has never happened to me before). He almost immediately announces that he’s shy and introverted. Oh my god. It seems that all that’s on the menu tonight is catfish??

But I’m not a total dick, and Melissa did say he was fun, so maybe this date is salvageable. And then: Winston starts talking through his résumé in painstaking detail. Beginning with his first internship. At age 19. At one point, I ask a question about the company he manages. “Oh, I’m not there yet,” he waves, silencing me while he takes a piece of bread, slops it in his food, and slurps it up, only to continue his chronological monologue of career highlights. Lovely. Now he’s telling me about a show he performs in…as a magician’s assistant.

An hour in, he pauses: “Wow! I’ve been monopolizing the conversation!” At least he’s self-aware? “So…” he shrugs. “What else do you want to know about me?”

I want to know when you lost all your hair, Winston. I want to know why you’re treating this date like an informational interview. I want to scream.

Saturday, 7:30 p.m.

I get a text: “Hey! I’m visiting next week!” Thank god.

Okay, I’m sorry, but…I’ve been keeping a little secret from you all. Remember my much younger Marine, Steve, who pinned my arms above my head for the hottest make-out and with whom I had a near-perfect date in D.C.? I’ve…actually been seeing him quite a bit since then. (Hey, I can’t fit everything into my column!)

Steve comes through town every few weeks, and it’s like cashing in on a rent-a-boyfriend subscription. We sleep completely entwined, walk hand in hand through the city, have amazing conversations, and have even more amazing sex. With his job and age and the distance, he’s sort of the opposite of the “good on paper” guys who can’t seem to keep my attention.

Friday, 8 p.m.

Steve knocks on my door and stands there, shocked, as I open it in nothing but lingerie and hand him a glass of whiskey. And here’s the thing, btw: I’m not doing this for him. I’m doing it for me. Because watching a man who looks like a young Channing Tatum stand like a cartoon character in my doorway absolutely incapacitated while ogling my body makes me feel, duh, great.

“Leave your clothes at the door,” I instruct as I pull him into my apartment.“Yes, ma’am,” he says as he quickly hangs his coat and even more quickly unbuttons his shirt and pants.

Steve picks me up, kisses me, and starts taking me to my bedroom. “No here….” I motion to the table. He cracks a wry smile as he gently lays me on my back and leans in to kiss me while dexterously removing my lace thong with his free arm. He leans down and slowly kisses my neck, running his tongue from my nipple down my body. He pushes my legs apart and flicks his tongue against my clit. “Oh my god.” I can barely muster words. His free hand is caressing my left breast, which, to be honest, is my better boob, and I savor every wave of the orgasm I’ve been looking forward to since I last saw him.

A super-quick shower together and I’m ready for celebratory drinks. He has big news: He’s graduating from Quantico and about to get stationed across the country, even farther than he already is and with even less free time. Which is so exciting for his career but kinda devastating for me. I guess I’ll just have to maximize what might be our last night together. When we get to the bar, I’m already horny again. I start surreptitiously running my hand from his thigh to his crotch while biting my lower lip. “Um, check,” he signals to the bartender. We’ve barely walked a couple of blocks when I push him against a store window. I’m stealing Steve’s moves from our first meeting and using them back on him. I pull down my top, fully exposing myself as I press my body against his. “You’re wild, Zara,” he laughs.

We have sex on my couch. On my table again. In my kitchen. The shower. And finally, the bed, where I fall asleep in his arms, wondering if what I’m feeling is real or just a side effect of the fantasy.

Saturday, 11 p.m.

“I got us a Revel,” Steve tells me as we leave a cozy brunch spot. I take the spare helmet and slide onto the back of his rented electric moped, living my best Lizzie McGuire life. He winds his way back to my place and steps off the bike.

“Is this the last time I’ll see you?” I try not to show how sad I am that he’s leaving. “I’m sure I’ll find my way back to you.” He kisses me one last time before fading—on moped—into oblivion.

Steve has been my relationship crutch for months—the hot, emotionally connected sex that’s just a train ride away. I acknowledge that. And maybe having this situationship officially off the table is the right way to close out what’s been an absolutely wild year: moving back to the city, trying to “find myself ” in singledom instead of jumping right back into a relationship, working through rejection, feeling every possible feel. All in all, it’s been kind of wonderful? So whatever 2023 has in store, I’m ready. And I promise not to keep any more secrets from you all…probably.

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