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The Reluctant Adventurer: 18 Dates in One Night

Friday, November 21, 2014


Illustration via iStock

A year ago, speed dating would’ve been my worst nightmare. But now, after a year of online dating, it was more like a pleasant fever dream starring lots of Members Only Jackets.

Can you even buy those anymore? Where are they getting them?

I’d been on OKCupid since February, and it just hadn’t been working for me. I’d met a lot of lovely men and even dated a few of them, but most of them seemed fairly shy. I hadn’t thought about it until I started meeting people, but it makes sense that the majority of men on that site are introverts—men for whom it’s agita-inducing to walk up to a woman at a bar or in the grocery store, but clicking a star on a website feels fine. 

I consider myself an extroverted introvert, but the problem is that I tend to be attracted to funny men. And while funny introverts aren’t impossible to find, I wouldn’t call them plentiful.  So there, possibly, was the rub. 

Additionally, it’s easy to tire of the ongoing Online Dating Expectation Revision Process (OODERP). This happens when, after a series of email communications in which the person is very funny and engaging, you meet them and realize that, in person, they’re approximately 40-70% less funny and engaging.  This is true of everyone, including me, so I’m sure my dates were tired of OODERPing as well. (This increased online and text wittiness can easily be explained by the additional time one gets for a digital response. You’d be amazed at the difference even a few seconds makes in a person’s cleverness quotient.)

So I thought Speed Dating would solve both of those issues at once. Only an extrovert would find talking to 20 people in two hours appealing, and these are total strangers, so I have zero expectations for someone to rip from my hopeful hands and stomp all over.

The event was at Jones Bar, which has a big square bar in the middle of the room that 40 people can comfortably sit around.

I tried to arrive almost exactly when the event was to begin to avoid having to talk to anyone ahead of time. I have never, in my entire life, approached a stranger at a bar and started a conversation with them. The idea of it makes me sick to my stomach. 

But this was different. We were all here for the same nausea-inducing reason, so it felt like I could approach someone and chat. 

“So have you done this before?,” I asked a blond woman with bangs who I decided was an elementary school teacher.

“Just once. We’ve both done it before,” she said, indicating the woman sitting next to her. 

“Did you ever read that book I was telling you about?,” she turned to her past-speed-dating buddy to continue their conversation before I could respond. 

“Hey! I have a LOT of friends. I think you should know that. I just couldn’t convince any of them to come to this, mostly because they’re all married or paired off and don’t tend to invite me to dinner because they think it’s awkward to eat with a single person which is so weird but that’s beside the point because what I’m saying is I’m fine not making small talk with you and while I appear to be crying, this is more of an allergy situation than anything else.”

I didn’t say that, but I may have thought it.

At 7:00, the Speed Dating Leader assembled everyone and told us how it would go: the women would sit at the bar by their numbers (I was 3), and the men would go from person to person, in numerical order, for five minute intervals ending at the sound of a bell.  We each got a sheet of paper with names and a space for writing notes. Next to each name is a “yes/no” that you circle, and then later enter on a website to see who matches you.

Not weird at all, right?


And so it began. 

My first “date” was a very nice, thoughtful guy who looked to be in his early 50’s with a daughter in another state. We were talking about how hard it was to stay close when someone lives so far away when the bell rang. I have no idea what he did for a living. 

Next up was a man who works for the city who bore a shocking resemblance to Ron Swanson, mustache and all. I heard about his job, but not much about his life. I realized immediately that when you have five minutes, you can either learn about their professional or personal life, but not both.

I found myself fighting making snap judgments about people. 

“This guy goes to Ren Faires, I can feel it.” (Or, he’s a very nice guy who works with HIV patients, jerk.)

“Giant gold watch? Really? Hello, douchebag.” (Hilarious, charming and probably not interested in me.)

“Oh, dear. This fella is definitely in the wrong age group.” (I was actually right about that, I think. Probably 10 years older than he should’ve been. He also offered “free hypnosis for women” and claimed he could bring me to orgasm using only his voice. Is there a way to click YES twice? Because there is absolutely nothing creepy about that whatsoever.)

There were sweet men and smart men and one who was either totally not interested in me or clinically depressed. 

What I mean by that is, when someone was particularly un-charming, or, say, appeared not to give a crap about anything, it was difficult to decipher whether this was the face he showed everyone, or just women he wasn’t interested in. 

I found myself taking far more conversational chances and being totally honest with the men I wasn’t interested in. Which isn’t to say that I was dishonest with the ones I was interested in—I was just willing to reveal more of myself when the stakes were lower. I wasn’t doing that dance of many veils where I shove down the parts of myself I think are unappealing or broken or, y’know, human so I can reveal them at my own pace. When the time is right. (Is “never” a good time?)

This unadulterated honesty lead to a fantastic, heated conversation with a financial planner about where he is in his current dating life. I essentially told him to stop dating bimbos. He may or may not have listened to me, because he clicked “yes” on my profile.

I would recommend speed dating to just about anyone, but not because I found it to be an effective dating strategy. (I clicked “yes” on two men out of 18 and only one out of the two matched me.) 

I’d recommend it because it’s probably the only time in your life that you’ll get a five-minute window into 18 people’s lives in two hours. What they do, what they love, who they probably still love, what they find appropriate to say to strangers and what shoes they think are appropriate to wear while saying it.

Additionally, I learn something on every date I go on about what I want and don’t want in a partner, so for me this was the dating equivalent of a low-residency PhD program.

I’m utterly shocked to find myself saying this, but I’d probably do it again.

Not anytime soon, however. It’s freaking exhausting.



RECOMMENDED FOR: Single people who don’t get nauseous when they think of talking to strangers, the loquacious, those who can hide their clinical depression until it’s appropriate to reveal it, extroverts.

NOT RECOMMENDED FOR: Introverts, nay-sayers and hypnotists.

Courtenay Hameister is the Head Writer and Co-Producer of Live Wire Radio, a syndicated radio variety show distributed by Public Radio International. She is currently working on a book that will be released through Audible.com in 2015. Follow Courtenay on Twitter at @wisenheimer. 


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