All The Ways I Overthought My First No-Strings One Nighter

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This summer was not the “Summer of Josh” that I had hoped it would be. What started with promise, enthusiasm, and a clear plan ended in broken dreams and unachieved goals. For a myriad of reasons, this summer was probably my least active in terms of meeting ladies. I had a few dates here and there but, I’m sorry to say, Alec Baldwin would forbid me from having coffee, for I was not a closer.

And so, a few weekends ago, I came to the end of my rope. With a dry spell stretching so far the State of California would be growing concerned, I made a desperate decision. I sent the Hail Mary Hookup Text.

In the past, I have sent the “all-in” text to a girl that I couldn’t figure out. This time, however, it was an even deeper ditch from whence I would cast my last effort. I sent a text, to almost every female I had gone out with in the past calendar year with the exact same message, the intent and purpose being very clear: are you up and do you want to have uncomplicated sex tonight.

This is the first time I’ve ever sent a mass text like this, for the sole purpose of finding another warm body for the night and not caring whose body that would be. I’ve had one night stands following a first date, or after parties in college, but those were by happenstance. This was a tactical attempt.

I am not proud to have done this, but I do not judge those of you who have. The experience was eye-opening and, most importantly, successful. But this tale is not about the destination, but the journey. So let me walk you through my night and all the minutia of this process that I, in my typical way, over thought it.

Part I: The Text

The first big decision I needed to make once I resolved upon this endeavor was about that mass text I would be sending out. To whom was a minor obstacle; it was basically every single girl in my address book that I knew lived in close proximity and who I didn’t care if I made an ass out of myself. Luckily, as someone with a lot of Tinder game but little-to-no relationship game, there were a lot of options.

Next, I had to consider the timing of the text. Send it out too early, I come across as a desperate Stan who’s spending his Friday night alone. But if it goes out too late, the pool narrows as most of the eligible ladies have already tucked into their Jumbo Slice, caught an Uber, and passed out in their own bed. Or worse yet, found another guy more funny and handsome than me they’d like to spend the night with (this is the part where all of you stroke my fragile ego and tell me that’s ridiculous, thanks). Eventually, I settled on a window between midnight and 12:30. Late enough that we were entering the “already out but winding down the night” phase, but not so late that last call was fast approaching.

Finally, the content of the message. A one-worder like “hey” or “sup” has a beautiful simplicity to it but is also easily dismissed. A longer message like “hey are you up? Doing anything?” comes off as too needy. The key is to craft a message where the subtext is hidden, but also obvious. Eventually, I settled on “heyyy, what are you doing?” Innocuous enough on its face, but the extra two y’s on the hey tell her the story I’m selling: out, drunk, and thinking of her.

And so, at 12:10 a.m., I began copying and pasting this message, combing through my address book, and casting lines, hoping for some bites.

Part II: The Response

To my surprise, the response rate on these texts was nearly half. I was assuming that maybe one or two girls would respond. Instead, my phone was pinging left and right. Now, before you all start patting me on the back, a lot of those responses ran the gamut from “who is this” to “screw you.” But for those who at least seemed open to the idea I was putting out there, I knew I needed to act quickly.

See, unlike a girl I match with on Tinder or Bumble, I don’t have the luxury of slow-playing this situation. The shot clock is counting down, and you gotta make every text count. Maximum efficiency. So how do I get this whole deal to happen in the fewest number of messages?

My first instinct was to say something cheesy like “just wondering if you want to hang out” but that is nearly maximum cringiness, only surpassed by a suggestion to “Netflix and chill.” But, as I noted above, the clock was ticking and I couldn’t afford to waste precious minutes (or texts) on pleasantries. To convey my intentions, but also express my apparent casual demeanor, I finally settled on: “I’m just hanging out and kind of bored. Want to meet up and do something?”

Part III: The Logistics

One of the fears that crossed my mind once I started getting multiple responses was how to juggle more than one perspective hook-ups in this precarious situation. Thankfully, my awkwardness managed to thin the herd down to one girl who was willing and able to engage in coitus.

She was a Bumble match I went out with over six months ago, for a grand total of four dates. It ended for the reason most relationships today end: lack of enthusiasm, short attention spans, and boredom. I have nothing bad to say about her and make no judgments of her enthusiasm to get down to business, but my first text that evening was our first communication since our last date. After our initial dance around what I was asking, what she thought I was asking, and what we both agreed upon, all that was left was the particulars.

Should we meet and grab a drink beforehand, or would that make it awkward? Whose house, mine or hers? Hers, she was very insistent on that.

Should I leave now, or go over a bit later? Did she want us to drink together beforehand, actually watch Netflix, or just get right down to business?

Luckily, she greeted me at the door with a near-instant drunken makeout session interspersed with several shots of tequila. Normally, I don’t imbibe that particular variety of poison, but since I was the away team I obliged to play by house rules. Once enough alcohol had been consumed and I had…revved her engine sufficiently. We not so smoothly made our way to the bedroom.

Part IV: The Aftermath

We lied there, somewhat sweaty, panting, and exhausted. We’d each done our part for the other, and I was ready to hang the “Mission Accomplished” banner over the headboard. But then the fog of horniness lifted, and I began to clearly see what situation was before me. All the desires and appeals that existed just a half hour earlier were gone, replaced by my original hope to be alone and not have to contact this girl again. The only question left was how to create a viable escape plan.

I wasn’t sure if it was permissible to just duck on out immediately at the conclusion, or if she wanted some post-game spooning. Whether there would be any awkward goodbyes, goodnight kisses, or empty promises to call each other to do this again. She gave me nothing, no indications whatsoever as to how she wanted to proceed. So I lay there, holding her, watching the minutes on her alarm clock change and wondering how many needed to pass before I could whisper the words “I think I’m going to get an Uber.”

When she left me at the door, we kissed goodbye, because it seemed appropriate, and made those empty promises to grab drinks that week. But that was the last time we spoke, almost two weeks earlier.

Only one nagging thought remained after the whole deal was said and done: what sort of opportunities for repeat performances exist going forward? I mean, we ended the night on friendly terms, and never had any big falling out after dating. I wouldn’t be so brash as to assume that I have carte blanche to ask again, but certainly, I believe that the door is opened to that possibility.

I don’t know if fall and cuffing season will drive me back to this situation. Maybe I failed to follow protocol and blew this shot. In any case, I passed through a rite of passage, and at least have some idea of what to do next time. Even so, I’m sure that I will over analyze it once again..

Image via Shutterstock

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Josh T.

Don't call me a liar, but you don't have to call me a truther.

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