Settle in, kids, and I shall tell you the tale of My Worst First Date.

Picture this: Me, young and fresh, a mere 20 years old and — this part is kind of important for what comes later — not a sex blogger yet. Just a gal looking for a good time. Full of hopes and dreams, not yet battered and bruised by the realities of the dating game. Maybe kind of a Libertarian, too, but let’s not dwell too much on that.

It’s my first day on a popular dating site that shall remain nameless. I’m so excited to receive a message that piques my interest that I hastily agree to a same-day date. We arrange to meet at the cafe where I work1.

It began in such a normal way. We briefly discussed him starting a graduate program at a local university in the fall, and my experience as an undergrad at the same school. When, after the typical this-is-who-I-am spiel, he asked if I wanted to hear a funny story, my reply was, “Of course!”

“You know the sex shop on 51, right? The one out kind of by Elizabeth? Well, I’ve been there a couple times.  I mean, who hasn’t, right?” 

At that point, I actually hadn’t, but I simply nodded along.

“So I went down there a couple weeks ago. Oh man, this is a good story. So okay. I’m going there for something very specific, you know? All right. I was in a year long relationship up until a couple months ago, so I got uh, pretty used to getting’ it on the regular, right?”

“Sure, that kind of thing happens. I’m really sorry to hear about the breakup.” I took an awkward sip of my coffee and looked around the café patio. The entire evening had begun awkwardly when he ordered nothing and insulted the café for being cash-only, then suggested we sit outside where it was a bit too cold for my tastes. Now that he’d brought up the seediest adult store in town, though, I had begun to feel grateful that we were on the relatively deserted patio.

“No big, she was a huge bitch. And I mean huge bitch. Like she wasn’t your size!” That’s when I started to feel it, like Botox. My face was immobile, caught in a pained, confused grin that might have begun to shift to a grimace. I couldn’t make heads or tails of where this was going. “Anyway. I finally bought a Fleshlight a couple weeks ago! All right so you gotta know, my parents are super conservative.”

“You don’t say! Wow, we must come from very different backgrounds, then. Hey, I remember on your profile you said something about a funny story related to the library? I’d love to hear it!” Good God, I tried. I really, really tried.

“Oh yeah, that! Ha. This is funny. So like, I went to this volunteer thing, and it was just full of old broads and one cop with like, one foot in the grave, I’m tellin’ ya. So they’re like, just wasting my time trying to teach me how to use Google, right? Seriously. So I’m like, ‘Hey, I want to fucking volunteer. Stop wasting my goddamn time.’ And the bitch in charge tells me that I can leave and they’ll call me about volunteering. They never called me! What the hell? 

Anyway, so I go into my room with this Fleshlight, still in the box, right? I have someplace to be that night, but I don’t want to risk my parents seeing it in case they go through my room. So I take it out of the box, throw it in a drawer, and put the box in my trash. Ok, so get this: I come home later and my dad just throws the box at me! ‘What is this? Didn’t we teach you to respect women?’ HA! So my parents think I don’t respect women. Hilarious, right?”

At this point, we were about fifteen minutes into the date. Our first date. (Our only date.)

Important note: Owning a Fleshlight is not a red flag. It’s totally normal. It’s fun, and as long as you’re cleaning it, it’s perfectly healthy. But everything else that he said? Red flag after red flag. The problem wasn’t the Fleshlight — the problem was the way he spoke about all of the actual, real, live women that he was referring to. Moving on.

“Wow. Well, that’s unfortunate.” I could barely choke the words out. Little mini me was so, so not prepared to call this motherfucker out.

“So yeah. Ha ha. What are you going to school for? How are the parties at Pitt?” 

Hopeful that we may have found a less fraught topic, thinking we might just pass the next ten minutes in relative peace and boredom before I could reasonably make a quick and tidy exit, I took the bait. 

“I’m actually going for my BA in economics. It’s pretty interesting. I think I want to get my Master’s in public affairs, maybe work for the government.2 The parties are pretty crazy, but I prefer throwing them.” I could only put off drinking the rest of my coffee for so long, and I downed the rest like a shot. The other patio patrons had disappeared, leaving us alone on Murray Avenue.

“Yeah, that’s pretty cool. I did poli-sci. Oh man, I got to tell you about this party I went to one time! Oh God. I came out of a blackout at this apartment I totally didn’t recognize and, get this… and this girl was having sex with me!” He laughed, as though that was not a massive consent violation.

Into which circle of hell had I inadvertently stumbled?

“You know, I think I need to run to the bathroom. It’s just inside. I’ll be right back.” Happily, it had been cold enough for me to wear my coat, which contained my phone, so I didn’t even stumble awkwardly trying to get it into my pocket inconspicuously.  As soon as I passed the windows that line the patio, I was dialing my friend Rob’s number. He picked up almost immediately.

“Praise Jesus. I’ve never had to use the emergency call before, but this ship is sinking fast. I’m parked here, but I don’t want to even give the dude a chance to walk me to my car. I’ve seen The Silence of the Lambs, and yes, I do remember that that was a moving van, but my car is a rather spacious sedan and I’m not taking chances.  …Please come get me?” 

“I’ll be there in ten.”

When you’re stalling, suddenly a million things become important. Do I have any loose threads? How are my teeth? Could I possibly make myself look slightly less attractive? (I never thought I would have to consider that one.) At some point, I sucked it up and headed back out.

“Sorry about that, I actually got a call from a friend while I was in there. But wow, I’m really sorry to hear that! That must have been very scary. I was actually just at this anything but clothes party where all of the girls had made dresses out of…” 

This was kind of like trying to guide a puppy for the first time on a leash, except puppies don’t generally sound like they could be felons.

“Aw, man, those are sweet. Easier to get ‘em out of their clothes if they’re not in ‘em to begin with, am I right?” 

…Definitely a felon.

“Uh… Sure. Nothing wrong with no strings sexI actually haven’t had one of those random party hookups, but I guess in theory…” I trailed off.

“Oh God, my back! Oh Jesus! Aw, fuck!” He shouted these as though someone had, moments before, shot him. (No such luck.) 

I jumped and without thinking, asked, “Good lord, are you okay?”

“Yeah, yeah, oh God. I’ve had these awful back problems since I had this job at Express last summer. Oh, God. I mean like, I think I was the first person ever to get a job simply by virtue of my status as a white person with a penis. You know? Like, white men are just so discriminated against. And because I’m just some white dude, they stick me in the back, lifting merch all day. It’s not like I’m not a fucking people person, not like I don’t know how to talk to customers, right?”

It was at this point that I started to suspect that this entire thing might be a farce, or maybe even performance art. There was absolutely no way that one person could be this revolting, right? (Wrong.)

“What on earth did you do to throw out your back?” I was too shocked and confused even touch the rest of what he’d said.

“Just lifting and shit. I don’t know. What’s it matter?” He was getting surly, and I wasn’t sure I liked this any more than I liked talking about masturbator sleeves. Blessedly, my phone said it had been eight minutes.

“You know, this is all super interesting, but like I said, I just got a call from a friend and it turns out I’m expected at this party tonight. I would love to invite you, but guys have to pay $5 cash and since you don’t carry it… Plus, I have kind of scary guy friends. You know, big guys, tattoos, shaved heads…” 

“Are you sure? I mean, I could drive you. You gotta hear the end of this story! Oh, man, like I remember coming out of that blackout and being like…”

A dirty green Subaru Forester pulled up, windows down, blasting Jay-Z. “Dang. It was nice to meet you. That’s my ride.”

And that’s the only time that I have ever run away from a date. Tell me the story of your worst date!

Disclosure: This post was sponsored by No Strings Sex and contains a link to their website, as well as an affiliate link to a retailer. All stories, opinions, and writing are my own. Sponsored posts help keep my content free, fresh, and produced in like, y’know, healthy living conditions.

  1. Note: I did not tell him I worked there. When I arrived early, I told my coworkers not to mention that we work together and instead to act like I was just a regular customer.
  2. Hahahahahahahahah