If You're Just A One-Night Stand, I'm Not Putting My Finger In Your Ass

For all of my lofty goals — like going on a date with someone more than once and having a guy to sit next to at comedy shows so they don't jam me in with a bachelorette party — there are some nights where I veer off the uneven concrete path of online dating and simply have sex.

The one-night stand, that glowing, beady-eyed demon in the corner of my mind reminding me just how much I'm disappointing my mother, is something that happens sometimes. And it is just that: one night. I don't expect (and, in fact, do not want) anything more to come of it. The one-night stand has its purpose here on earth, and it is a brief one: We're having sex tonight, and I don't want to speak to you anymore.

You should know that this is also the only way I have sex. The life of a single woman in her 30s is often a sexless one. For every 10 first dates I go on, maybe one turns into a second date, maybe two per year turn into third dates and that's typically it. I don't find myself in a ton of situations where I've known a guy long enough to “appropriately” have sex with him.

That is, unless you count my male friends. But every last one of them is either married, in a long-term relationship, gay or a medical professional of some kind bound by oath not to sleep with me. How, then, am I supposed to have sex? This way. This horrible, but also wonderful, modern-day dating practice.

One-night stand sex is nothing if not simple and to the point. I'm not going to stalk you. I have no plans to text you tomorrow. You're not going to see me liking your photos on Instagram from 33 weeks ago. I simply don't care that much. Every detail we discuss tonight will be forgotten before my Uber reaches my zip code.

If I'm participating in a one-night stand — if I'm actually seeking one out — it's most likely because I'm entirely fed up. I've had one too many bad dates recently, or I've had several good dates that turned into absolutely nothing at all. I'm in a no-win state, and I'm over it. You could potentially see it as rock bottom, but I prefer to think of it as some enlightened fifth layer of the church of online dating you can only get to by dedicating your life to it for five years and paying your annual $39.95.

Such was my mindset when I matched with a visiting blonde lawyer on one of my good ol' dating apps. Let's break him down into his various parts:

Blonde: My favorite flavor.

Lawyer: Gainfully employed, implied work ethic after the seven years of education and bar exam it takes to simply draw a salary as a barrister. I like talking to people who work in an office. We all have a similar outer crust of grumpiness and world-weary tales, and we all really miss "The Daily Show with Jon Stewart."

Visiting: And here's the keyword. The first box on the one-night stand checklist that lets you skip right down to the bottom of the form. He doesn't live here. He's in town on business. If he's out on a date with you, he has zero intention of asking you out again because by the time that would be possible, he will be back in his Brentwood apartment lifting his feet so his cleaning lady can vacuum underneath.

When I'm looking for a one-night stand, visiting men set my mind at ease. I won't even spend one minute after the date wondering when he'll text me again, unlike the days I spend in that purgatory following a normal, zipped-up date. I know he's not going to text me again. He knows I know that, too. We're in the same headspace, so there are no lies happening here. Call me crazy, but co-conspired one-night stands might actually be the most honest thing that happens in the online dating world.

Another subtle clue that both parties know how the date will end before it starts is the pace at which plans are set. If the first contact we have with each other is at noon, where we make plans to see each other after work that day, combined with his visiting status and my status as a local, actively dating girl who knows way better than to make same-day plans with a visitor unless she plans to end up naked at some point in the near future, this is happening. It's code. It's unwritten rule. It's what they'll find left on the walls of our caves 500 years from now.

We met at an oyster bar, also a good choice for one-night stands because a full dinner isn't what happens. It isn't what needs to happen. A few items off the raw bar, a bowl of olives and good wine. It's more elevated than slamming back an Old Fashioned at a cocktail bar that took decorating lessons from a club in Vegas, and less obvious than dive bar beers-n-shots. I'll take a good oyster bar any day.

The date was actually fantastic. We had an impressive amount of likes/dislikes in common, and I didn't find his legal practice area coma-inducing. He was ridiculously good looking. He looked like he arrived at the restaurant via Ivy League rowboat. More than once, we actually forgot we were on a one-night stand and really talked to each other. We snapped back to reality super quickly though, don't worry.

As the wine glasses neared an empty state, he suggested we “get out of here.” When I asked where exactly he thought we were going, a simple answer came: “My hotel.”

Hotel sex? For me? This is an embarrassment of riches! No Airbnb sex amid someone else's sheets and family photos for this guy. We're talking 3.5 star Midtown hotel. Nothing but the best.

The hotel was very old and wasn't renovated, the kind of place where the front desk person isn't savvy enough not to give you judgmental eyes as you take the elevator upstairs with a guy and back down again alone 1.5 hours later.

After we got off the elevator, we took so many turns down so many hallways I wondered if I shouldn't leave a trail of Altoids to find my way back again. I expressed my concern, but he assured me that he'd “walk me out.” Such a gentleman. Again, no pretense of sleeping over, no mask of “what are we doing here." Just pure function, plan, procedure. And that's what we did.

But then, around 15 minutes into having sex, something happened that went against the entire notion of the one-night stand, though I'm fairly sure he didn't see it that way. He probably thought that a girl willing to get after it on the first date was something of the sexually adventurous type, and he could go ahead and really open up.

In my mind, I thought we were having good, old-fashioned American sex. In his mind, however, he thought it was perfectly acceptable to say, “I want you to stick your finger in my asshole.”

... Honey, I want a lot of things. I want a nicer apartment, hair that never goes gray and vacations in Europe twice a year. I want a personal assistant, a closet full of Reformation dresses and a boss who doesn't text me at 9 am on Sunday mornings.

But mostly, I want a boyfriend. I want someone I have sex with more than once, someone I don't have to worry about getting a text from again because he's chosen to spend the whole weekend with me, so texting is entirely unnecessary. He can just look to his left and speak. I want someone who learns what I like and don't like, sleeps next to me after having sex, makes me breakfast tacos in the morning and knows what breakfast tacos are because he's probably from Texas, too.

That's the kind of guy who gets to ask me to stick my finger in his asshole. Not you.

You don't get to ask for that. You've done nothing more than buy me three glasses of wine, two oysters and a prawn. You have done absolutely nothing to deserve sexual acts that terrify me. While I'm thrilled that straight men are opening up to the idea of their own assholes being on the sexual table, rather than just asking for anal sex from their girlfriend on their birthdays, this particular action is something only someone who commits to me can request.

A one-night stand cannot ask for things a boyfriend gets. He shouldn't pretend, even for a mere moment, that he's entitled to what a husband can have. A one-night stand needs to know his place. He needs to know why we're here. We are not here to make sure he gets to enjoy the sexual minutiae his last girlfriend introduced him to.

You, as my one-night stand, are entitled to one solid, mildly drunken lay that culminates in orgasm (if I'm lucky, this applies to both of us). You're already getting a pretty good deal here, don't push me.

My boyfriend can ask for whatever he wants. I will fulfill the sexual desires of someone who has introduced me to his family. Someone who remembers not only my birthday, but also the day we became a couple. Someone who has elevated himself from a guy I have to make specific plans with to someone with whom steady plans are implied. Someone who has helped me put the sheets back on my bed on laundry day. Someone who bought me a ticket to an event of some kind without asking me first because he's in a relationship, and when you're in a relationship, you buy two.

He knows I always prefer to sit at the bar. He knows I will not see rom coms in the theater. He knows I cannot sleep in a hot room. On a road trip, he can walk into a convenience store and come out with something I'd like that I didn't have to request. He misses me when I'm away. He actually wants to spend time with me — a lot of time.

That's the man who gets the benefit of me. He gets meals cooked for him. He gets taken care of when ill. He gets to pick the Netflix. And yes, you confused tourist, he gets a finger in his asshole if he wants one. Because he earned it.

You're just a one-night stand. You haven't done shit.