Cosmo's Official Dating Diarist Gets Threesome Advice From Her Ex

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

Catch up on Chapter One

Tuesday, 6 p.m.

I’m texting with Ethan, the unfairly sexy ethically non-monogamous gentleman who proposed a get-together with me…and his girlfriend. Focusing on coordinating three different schedules is keeping me from spiraling into an Am I ready for this?! hole when, out of nowhere, my ex-boyfriend James invites me over for a wine night catch-up.

This seems dangerous. I haven’t seen him in two years. He’s the guy who, eight months after our breakup, texted me: “There’s a question I’ve been dying to ask you.”

His actual question, which came through just moments later, was: “Is your butt real?” I know. But I’m not doing anything tonight, and I sort of can’t resist the chance to remind myself just how much better off I (probably) am without him.

I cautiously walk into his all-white apartment. The decor seems too minimalist for what a chaotic person he is. He hands me a glass of chilled red and begins a play-by-play—of his career, who he’s dated since we broke up, all the minutiae I missed. Are we…friends now? This man once broke my heart, but right now you’d think we’d been lifelong pals.

He asks for my updates and I can think of only one thing: “I have a date next week with a couple.” I figure nothing says “I’m over you” quite like mentioning my quest to become some pair’s unicorn. James pauses, then says, “Always find a task, and you’ll be fine.” I did not have “get a pep talk from my ex-boyfriend for my upcoming threesome” on my 2022 bingo card, but a tip is a tip.

I’m quite pleased with myself as I leave. Have I achieved the impossible? It’s pouring outside, and he lets me borrow an umbrella. I soon get a text though: “I guess I’ll have to see you again to pick up my umbrella. ;-)” Yeah. And honestly, it’s just the thing I need to propel myself right into a throuple.

Thursday, 7 p.m.

Holy shit, I’m on the date. We’re sitting interview style at a cozy Italian restaurant in Williamsburg. Me on one side of the table, them on the other. Ethan’s biceps are barely contained by his cap-sleeve shirt. His partner, Heather, is at least 5’8″, tan, with dark, curly hair and piercing green eyes. She’s New York hot. I’m Boston hot. These are fundamentally different categories.

He orders pasta for the table. I self-select into an entire wedge of cheese haphazardly grated onto my Bolognese and pray my dairy-sensitive stomach can handle it.

And wow, I like them. They’re thoughtful. Intellectual. Fascinating. Our conversation is running the gamut from political theory to technology to their own journey establishing the boundaries around their partnership. They’re expert communicators with each other when it comes to figuring out what they’re okay with, and it’s both comforting and kind of inspiring. Have I ever actually talked this openly or clearly with a partner?

My favorite part is the couple sitting next to us on a completely traditional date listening in on our much more interesting date. They’re not even pretending to speak to each other. Instead, they keep looking over in a combination of horror and anticipation and silently making eye contact to confirm the other has, in fact, heard what we said.

Thursday, 9 p.m.

Dinner is done and I’m in the bathroom feverishly texting my group chat. It’s now or never. Ethan and Heather are either inviting me back to theirs or telling me it’s been a nice night.

I get the invite! We go to their spacious loft that’s equal parts tropical Miami and mid-century Brooklyn. Someone compliments my butt (which, to answer James’s earlier question, is very much real). Maybe I’m not bringing down the group average after all.

We walk onto their private roof and I wonder if they host sex parties here. Then my anxiety hits an all-time high. Is it too late to leave? Yes. If there’s one thing I struggle with more than lactose, it’s widespread knowledge of my own defeat. I had told too many people. I was now too big to fail.

They offer me a weird tincture that’s allegedly a sexual stimulant. Who am I to turn down some good old Brooklyn hospitality?

Ethan leans in and kisses me. Heather is standing next to him, ready to take his place as he pulls away. She smells like expensive vanilla. Her touch is soft, gentle, romantic. A welcome contrast to Ethan’s firm grip. Why have I been tolerating years of ragged beard burn when I could have had this?

We relocate from the roof to their bedroom. I’m not going to lie, I studied for this moment. I binged MFF porn to understand what I was supposed to do. I work in operations­—I needed a full run of show.

They have a massive mirror opposite their bed. I’m on the edge of the bed facing my reflection as they kneel on both sides of me, taking turns removing my clothing and touching me, grazing my neck, my breasts, my stomach. In an embarrassingly short amount of time, my body begins to writhe with intensity. Maybe the tincture actually did something.

My normally hyperactive brain quiets into the present, focusing on their distinct rhythms. I don’t even need to think through the advice my ex gave me. The whole thing is so much more intuitive than I expected. Throughout our multi-hour ménage à trois, I alternate between being the nucleus and the electron of the group. Our last event of the evening is Heather’s request: She wants to watch me and Ethan.

As we all lie there, sweaty, flush, calm, I realize I would have enjoyed this experience just as much, if not more, if Ethan hadn’t been a part of it.

Friday, 12:30 a.m.

I’m home and self-righteously updating the 13 friends who guessed I would chicken out of this experience that their doubt was misplaced. I’m triumphant.

I go on Bumble and switch my profile to women. Why not? I’ve dipped a toe in sapphic waters. What else is out there? Five swipes in and I see her: tan; dark, curly hair; wolflike green eyes. Heather. Do I swipe? What are the rules of engagement in an ENM partnership?

I’m conflicted. You know when you have an experience that is so great, you just want to leave it be? And what if she didn’t like me? Fear gets the better of me and I swipe no and close the app. I have Ethan’s number. I can find her again.

The Next Saturday, 9 p.m.

Three friends and I are cabbing downtown toward a casual house party and I’m in my grungiest turtleneck. After one of Those Weeks at work, I am so not in the mood for physical contact that I preemptively did not shave any part of my body, solidifying my goal to repel people this evening. (Listen: In the abstract, I am a huge feminist, completely supportive of women celebrating their own body hair. But in the practical, I have not yet achieved that level of feminist freedom.)

But, oh. While en route, we get invited to crash a seriously tempting private soiree later tonight. Suddenly I’m feeling very “Why did I wear a grungy turtleneck out on a Saturday night?” I know I did this to myself.

I am not a trained stuntwoman, but I basically leap out of the car to run home and change. My friends are convinced that I will fall asleep when I get there. It’s true, I do like naps, but this time I will make it back out. I put on a long-sleeve mesh black top over a black bra. I’d already set my “no attention, please” intentions for the evening. Except now, my outfit and my intentions are at odds.

Saturday, 10 p.m.

I arrive at the house party (to the awe of my friends) and see a familiar face at the doorway and freeze. Didn’t that kid bully me in high school? Yes. Yes, he did. You know what though? In a single moment, I have gone from being an atheist to strongly believing in a higher power. Because tonight, I almost ran into my high school bully in a turtleneck, but instead I’m rocking the hottest outfit I own.

Sometimes I have these out-of-body experiences where, for a split second, I see at the same time both 14-year-old me being pushed against lockers and called ugly and 20something me gallivanting across New York City dating pro athletes and finance bros. I wish I could go back and give tween me a hug and let her know that it will, in fact, get better. Or at least more enjoyable. Someone once described me as a former musical theater kid who suddenly became hot and had no idea how to navigate it. They were not not right.

Saturday, 11 p.m.

The soiree in question turns out to be an all-male college club’s reunion night. As I’m vibing on the dance floor, a hand slips over the small of my back. I turn around….This kid can’t be more than 19. I’m equal parts entertained and impressed by his confidence. I ask how old he is. “I’m a sophomore. Just turned 19.” Called it.

I ask what makes him think I’ll go home with him. His verbatim response: “I can rock your world.” If anything, I applaud his balls. The question is, have they dropped yet? As much as the idea of getting jackhammered for two minutes seems titillating (eye roll), I politely decline.

Sunday, 12 a.m.

We’re regrouping at a friend’s apartment before heading to the after-party.

A man beelines for me in the corner and introduces himself as Steve. Oh, wow. I hadn’t noticed him earlier at the club. He’s tall, muscular, with impeccable posture. He’s a Marine, back for the weekend before returning to Quantico in the morning to continue his training.

Based on the drunk mental math I’m trying to do, piecing together a timeline of his life, I think there’s a five-year age gap here and he’s younger. I find myself comparing him to Heather, who keeps flashing through my head at the least opportune moments. I’m still mentally committed to going home alone—it’s like I don’t want to wipe out that sexual memory with another just yet.

The after-party turns out to be us sneaking into an NYU concert, where everyone’s dressed in jeans and ironic T-shirts. I’m with 15 dudes in tuxedos. We look like idiots. But Steve and I dance for hours.

Sunday, 3 a.m.

We’re leaving the concert. Our friends are steps ahead. “Do you want to see a move from Quantico?” Steve asks. Before I’m even done nodding, he pushes my body toward a shop window and pins my arms above my head. I am literally, and figuratively, disarmed by him. He kisses me passionately. Our chemistry is out of control.

My friends don’t even notice. Either they’re too drunk or he’s just that stealthy. He picks me up like I’m a weightless backpack. This is one of the hottest make-outs of my life. Why didn’t I shave my legs?

It’s always the nights when you commit to meeting nobody that you end up finding someone great. He’s funny, charming, inquisitive. But he’s leaving New York tomorrow. I look up and realize we’re only six blocks from my apartment. We start walking home. I guess I can think of a few more activities we can squeeze in before he goes.

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