Cosmo’s New Dating Diarist Has Gone on 300 First Dates

Photo credit: The Scissorhands - Hearst Owned
Photo credit: The Scissorhands - Hearst Owned

*To protect the innocent (and the guilty?), her name is not actually Zara Field. In fact, all names have been changed.

Thursday, 4 p.m.

A notification pops up: “Am I still seeing you this evening?” Relief.

It’s move-in day at my new apartment back in Manhattan. Yes, “return to office” is finally happening—and with it the end of my vagabond lifestyle. As the movers unload the last of my boxes, I sit with an uncomfortable realization: I already hate living alone. An unbridled extrovert, I crave having other people in close proximity, something I’d gotten accustomed to over a decade of living with roommates.

Paul, the plastic surgeon I’ve been sort of seeing, says he made a reservation at a Greek restaurant on my block. It’s a good thing he picked somewhere close, because I have plans to put his dexterous hands to good use afterward (by helping me secure the fitted sheet to my bed).

We met two months before I moved back to the city. He’s hot in a pretty way. Like, very symmetrical features and Jimmy Neutron–esque swoopy hair. He’s on the scrawnier side though, and I think his calves are thinner than mine. I slept with him on our second date to avoid another night on a friend’s very underfilled air mattress. And I’ve continued to sleep with him on every visit to NYC since.

His background in medicine means he knows the curves of my body almost as if he’d sculpted them himself. But his hyperanalytical, direct nature also means he has an undeniable talent for ruining my orgasms with poorly timed commentary. Like when I asked him to use a vibrator on me only to have him stare at my vagina with wonder and say, “Can you believe babies come out of here?” No. I can’t. Also, I plan on having a C-section, so this Rabbit is the closest thing my vagina will know to childbirth.

We’re already dangling between situationship and relationship, and I honestly don’t know which way I want it to go. Why, and I cannot stress this enough, the fuck did I get a college minor in the psychology of sex and relationships if not to make me superior at these kinds of decisions?

But for now…dinner!

Sunday, 6 p.m.

“You don’t even like him. Let him go.” My tarot card reader habitually tells me I’m making bad decisions in my love life. I tend to agree…and then barrel full steam ahead on my previously charted path of self-destruction. It’s no different with Paul.

This despite the fact that over the past decade, I have gone on somewhere between 200 and 300 first dates, collecting unfathomable amounts of data across a diverse pool of prospects. CEOs, actors, pro athletes, lawyers, crypto specialists—you name it, I’ve dated it. I’m like a truffle pig for red flags, constantly sniffing out long-term incompatibilities. Enthusiastic about giving oral? Nonnegotiable. Someone who claps when the plane lands? Deal breaker. My love language? It’s touch, but I’ve started telling them it’s gifts.

There are plenty of moments with Paul that ring baby alarm bells: the slightly-too-long lulls in conver­sation, certain frustratingly myopic viewpoints, his distinct Long Island accent that hits my misophonia-cursed ears just the wrong way.

But he also treats me incredibly well. Proactively makes plans. Received the highly coveted Friend Stamp of Approval, an honor few have achieved. And he’s the best dancer I’ve ever dated. He spins and twirls me on the dance floor like he’s auditioning for Dancing With the Stars. I also really like sleeping next to a warm body, sooo…for now, I’ll keep him.

One month later

Paul invites me and some friends to his house outside the city for a party.

I hadn’t considered the possibility that his entire family would be there. Yes, even his dying grandmother. It is an ambush. And one that I’m entirely unprepared for, as indicated by my plunging neckline and the $29 bottle of vodka sweating in my arms as a now-wholly-inappropriate host gift.

My anxiety is skyrocketing. I’m not ready to meet his parents. I’m not even sure I want to date him exclusively.

Being there, seeing the type of future we would have together…it’s clear that my tarot card reader is right. The micro-incompatibilities I’d downplayed before now shine as brightly as the glass centerpiece on his sweet little family’s dining table. I realize I have tethered myself to Paul out of fear of loneliness, not out of potential for love. Damn.

Photo credit: The Scissorhands - Hearst Owned
Photo credit: The Scissorhands - Hearst Owned

The next day

As tempted as I am by the idea of free Emsculpt and Botox forever, I call Paul and end things. (Sacrificing a lifetime of filler in pursuit of more consistent orgasms? Some might call me a martyr.) He handles it gracefully. Classic, kind Paul. Did I make the wrong decision? He really is a gem.

Two weeks later, Wednesday, 12 p.m.

I decide that in tandem with living alone for the first time, I need to commit to being unpartnered for at least six months. No clinging to the safety net of companionship as I navigate the transition back to the city.

One hour later

I am swiping on Raya with abandon. Business mogul with jet-black hair and olive-toned skin? Sign me up. Drinks? Rooftop bar? Tonight? Done.

Later that night

We’re escorted to the back corner of a nearly empty jazz lounge. We have our choice of seats: an oblong love seat, two chairs facing each other, or a bench. We end up sitting side by side on the love seat. His hand is grazing my leg halfway through his first old-fashioned.

Our second drink arrives and he’s already whispering in my ear, inviting me back to his place. This is escalating faster than I expected.

There’s a yoga mat in the center of his living room, and I sit on it in a position that I, a former camp counselor, call crisscross applesauce and Google calls sukhasana. He sits across from me and immediately begins to take off my shirt. I reciprocate and ask about the olive branch tattoo on his stomach. He explains the symbolism of the tattoo, something about peace and hope and how it relates to his roots.

Then we’re naked on his floor. I hate yoga. But this I like. I climb on top of him, wrapping my legs around his body. We rock slowly back and forth, never breaking eye contact. We flow through sex poses in tandem. It’s intimate, slow, connected. I’m following his lead. Does sex on a yoga mat count as meditation? My soul is enlightened, but my knees are paying the price. He carries me to bed.

I quickly scan the bedroom. Why doesn’t he have curtains on his windows? Odd. Never mind. Focus. He has my full attention. Sort of. Who doesn’t have curtains? He picks up his pace, riding harder and harder until he suddenly pulls out and I feel warmth on my chest. We take a quick shower, and I fall asleep nuzzled into him.

Thursday, 6 a.m.

The afterglow of the night comes crashing down around me when he abruptly wakes me up. I am many things, but a morning person is not one of them. He keeps pulling my hand toward him, trying to initiate another round. Half asleep, I cocoon myself more tightly in his cozy comforter, wedging a physical barrier between us. My attempts to rebuff his touch are met with surprising aggression. He is agitated and gives me an ultimatum: Have sex with him or get out of his apartment so he can start his day. He may as well have injected espresso straight into my veins. I get up, gather my things, say goodbye, and hurry down the stairs. I don’t even fully secure my left shoe until I reach the street.

I walk a few blocks, inhaling the muggy city air, and start to type: “Hey. I had a great time last night. With anyone I’m dating, it’s super important to me that if I voice a boundary of not wanting to be touched, it’s honored. It’s difficult to continue seeing someone if I feel like that boundary’s been crossed.” Send. I inhale. It’s sad how quickly I can draft a version of that text.

He apologizes, says he won’t do it again. But we both know the olive branch has been rescinded.

Saturday, 2 p.m.

Back on Raya. I swipe on Ethan. Ethically non-monogamous? I’m intrigued.

Ethan is an early-40something with either a six- or eight-pack, it’s hard to tell. Is it even fair for me to swipe on someone this fit? These days, I consider walking from my bed to the kitchen table exercise.

It’s a match. This is the confidence boost I need today. Or maybe I’m a catfish, using photos from a time that I also had some perceptible ab definition.

Ethan surprises me. He’s down-to-earth, thoughtful. He’s even giving me recommendations for my trip to L.A. This is an actual excerpt from our conversation. Ethan: “Did you make it to your flight today?” Me: “I am getting on this flight whether my stomach agrees or not. I might take a sleeping pill and then accidentally shit my brains out but we shall see! It’ll be an adventure.” Ethan: “Hahaha wishing best of luck to you.”

Sometimes I think my allure to men is that I give zero fucks what they think of me. To wit: After my flight, Ethan asks me out, so we set a date to grab dinner in Brooklyn. Then he hits me with it: “We can’t wait to meet you. My girlfriend thinks you’re hot.” I go back to his profile. Amid the alphabet soup of ENM (ethically non-monogamous) and GGG (which I had to Urban Dictionary and apparently means “good giving game”) he’d listed, I had missed the unicorn emoji, the signal that they were seeking a third.

Did I just accidentally commit to my first threesome? Frankly, I’m surprised that I haven’t checked off the obligatory 20s Threesome Experience yet. Well, there was one failed attempt in Rome in 2015 that almost compromised a seven-year friendship…but since then, it’s been at the top of my fuck-it list.

And this could be my first real experience with a woman. I struggle to reconcile this disconnect in my own sexuality, where despite being so open-minded and adventurous, I have also clung firmly to the heterosexual space of a 0 on the Kinsey scale. To be clear, I am actively trying to move up on that scale—I would like to migrate to at least a 1.5 or 2. But at the same time, what would I do with my hands?

“Just to set expectations, I’m totally new to this,” I text. Ethan responds: “Don’t worry, enthusiasm goes a long way.” Okay, Ethan. How about anxiety? Does anxiety go a long way?

Two weeks later

As an exercise in accountability, I tell some friends that a threesome with a couple is on the table and collect bets on whether they think I’ll go through with it. In a shocking vote of no confidence, I receive 1 yes to 13 nos. My Vegas odds are roughly the same as Regé-Jean Page becoming the next James Bond: a highly desirable yet low probability outcome.

Still. Ethan, his girlfriend, and I are set to meet for a throuple date over plates of pasta and goblets of wine. May the odds be ever in my favor.

Pick up Issue 4 of the magazine to see what happens next.

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