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The Reluctant Adventurer: The Year of Dating Totally Un-Dangerously

Friday, January 23, 2015


Last year on January 4th, I posted the following status update on Facebook:

"Friends: I, like millions of people across the country, have recently signed on to a dating site in an attempt not to die alone. If you can help me to avoid going on more dates with boring strangers who speak about themselves in the 3rd person, please introduce me to your favorite single un-crazy friend (or, your single friend who is f*cked up in a way that you believe complements the ways in which I am f*cked up).

I appreciate your attention to this matter, and because you've taken the time to read this, I've included this photo of a kitten posing like a pinup girl for your viewing pleasure. Weird.

Now back to your regularly scheduled posts about how much people love their lives and stuff."

You may be thinking, “Wow. How could she possibly post that? I'd be mortified.” 

Let's look at an equation that may explain where I was at the time:



Loneliness + Encroaching [Old Age] – the Ability to control Gravity [is greater than] the Possibility Of People In My Life Knowing the Depths Of My Aforementioned Loneliness and Fear of Dying Alone.

I wish there were a different word for the brand of loneliness that comes from being partner-less in a partnered-up world. (Untethered? Genitally Unattended-to? Terminally Unaccompanied?)

Some way to quickly communicate the strange juxtaposition of being happily surrounded by people you love and grateful for their presence while periodically sobbing in your driveway after returning home from a party because Gillian Welch's “Dear Someone” grabbed your chest through your car stereo.

It's a loneliness that comes with a tremendous amount of guilt for not recognizing how lucky you are to have the love you do have and for looking like one of those women who's so weak that she can't be happy without a man. 

I was happy, overall. I am happy. 

I just periodically sob in my driveway and would rather not do that. That doesn't seem unreasonable.

So that explains the mortifying post from a year ago. 

Since that post, I've been on 28 first dates.

I know that sounds appalling, but that's only because it is.

The first site I signed up for was Tinder. In retrospect, it wasn't really the site for me.

Tinder is supposed to be the straight world's answer to Grindr (a hookup app for gay men) so it probably wasn't the best choice for easing back into the dating world, but a friend had some success with it so I tried it.

The Ethical Slut

I'd met a couple of guys through the app, one of whom was adorable and fascinating in his no-nonsense approach to dating. He was a self-described Ethical Slut who was looking for a Trinity of women who could each provide for a different need in his life: one for social events, one for sex and one to be a playmate in his various athletic pursuits.

He was so earnest and believed so strongly in constant honesty that it was sometimes jarring. 

About an hour into our first date, he leaned into me at the bar and said with a wide, enthusiastic smile, “I think this is going really well. Do you think it's going well?”

I. Um. I don't know! There's a lot of stuff going on right now. I'm still trying to figure out what I think of your hair. 

We dated casually for a couple of months, both being clear that we were seeing other people and knowing this probably wasn't leading anywhere. He asked me in an email how my other dates were going.

“Fine, I suppose,” I wrote back. “But I'm so tired. It's exhausting trying to appear charming for that many hours in a week.”
“I know,” he replied. “Dating is exhausting. But if you can find one or two people you enjoy going out with and bringing home and then sending them home so you can get some work done, then that's success.”

I told him it was the most romantic thing anyone had ever said to me.

Nothing like hearing exactly what you don't want to get you a little closer to what you do.

Text Guy

One of the people I'd attempted to be charming with around the same time as the Ethical Slut was someone I called Text Guy. 

He had asked me out after reading my humiliating Facebook post, but for various reasons couldn't meet in person for a couple of weeks, so we texted each other. 


He was smart and very funny and I immediately fell in deep like with the digital version of him.

When we finally went out, our corporeal selves had to catch up with how far our digital relationship had progressed. I knew all about his family, his difficult work situation and his most recent heartbreak before I ever shook his hand. 

On our first date, he said if things went astray we could always just turn our backs and text each other. 

Turned out it wasn't necessary for me. I was even more smitten with him in person. 

He was 6' 4” with bright eyes and a wickedly handsome smile. He was also 9 years younger than me.

After four dates, one in which he spent the entire date trying to warn me off of him, it became clear He Just Wasn't That Into Me. 

But it was confusing, because his text behavior was that of a very interested person, spending a good hour or more over the course of each day communicating. I think he enjoyed the banter and didn't want to lose that, so even when he was losing interest physically, he kept up the text relationship right up until the end. 

He ended the relationship via text, which I was initially angry about, but in retrospect it made perfect sense. 

The physical versions of us barely knew each other, it was our digital selves who were the most intimate, so they were the ones who required a breakup. It was only logical, but the physical version of me was stung.

That was my first minor heartbreak of the year, and it was only February.

Wait List Guy

Text Guy was followed by Wait List Guy.

He was a sweet, funny and curmudgeonly-in-the-most-charming-way designer who unfortunately started seeing someone exclusively just as we were trying to set up our first in-person date after chatting on OKCupid. He agreed to meet me anyway, since I was technically sort of grandfathered in.

Over the course of the ensuing months, Wait List Guy and I would meet for drinks and talk for hours, mostly about my dating trials and how much he hated his job. 

I called him Wait List Guy to my friends because even though we were just meeting as friends, part of the reason I initially wanted to hang out with him was that he'd just started seeing this other woman, so I wanted to make sure I was first on the waiting list if it didn't work out. 

Is that something a sociopath would do? Probably. Was everything we ever did completely platonic? Absolutely. Would I have made out with him the second he told me they'd broken up? No question.

It wasn't really a black and white situation, but how often do you get those in the dating world? 

Now, after almost a year, Wait List Guy has become Sweet-Curmudgeonly-Friend-Guy. We've settled into about a once-a-month catchup wherein he calms me down and I entertain him with stories that reinforce his decision to remain in his warm, snugly committed relationship.

The Spring Guys

The Spring saw a series of one-or-two-timers: Tall Uncomfortably Quiet Guy, Entitled Guy, “Guy-Who-Doesn't-Know-What-He-Wants” Guy, and my favorite of the bunch, a guy whose job was to climb Oregon's largest trees and measure them. 

He didn't like me. Which is weird, because I'm so outdoorsy. (I am not.)

The Summer Guys

The summer wasn't much more successful with the appearance of Inappropriately Judgmental Guy, Lovable Meth Guy, No Ambition Guy, and Namaste Guy, who I'm pretty sure was overtly glaring at me at the end of our two hours together. (He thought all humor had to be “at someone's expense,” so he didn't find my “jokes” very “amusing.”)

I did develop a pretty great new technique around July: uncontrollable nervous flop sweat during the first 30 minutes of a date. Never happened to me before, but has since become my go-to method for making an unforgettable first impression.

The worst was my first date with “Radio Guy” as we sat outside at the Bye and Bye, a surprisingly good vegan bar on Alberta Street in Portland.

I was wearing a low-cut sun dress with spaghetti straps, and when the sweating started, I could feel it running down either side of my head. It then formed two tributaries—one below each ear—and flowed into a giant estuary that ran down the center of my cleavage to a great Salt Lake in the center of my bra. 

As I talked to this lovely person who I had a lot in common with but no huge spark, I tried to figure out what sort of subtle gesticulating I could do with my hands to cover up the surface runoff coming from what felt like every pore. 
If I covered my cleavage, he could still see my neck, if I covered my neck, he could still see my ears. I thought about telling him that he'd just caught me coming out of the shower, but that's a difficult story to sell when you're sitting at a picnic table outside a bar.

I finally just let it go, and thought, “Well, he either likes sweaters or he doesn't.”

Turned out, he liked sweaters. 

Shockingly, after that inauspicious beginning, he and I spent a lovely August drinking summery cocktails and enthusiastically making out, until I had to take a break to work on my book and we just fizzled out.

Oftentimes these days, there's no real end to a coupling, there's just “ghosting.” That's when one or both people simply disappear from text communication. Sometimes there's an “illness” or “business trip” involved, but I've been ghosted a few times and am embarrassed to say I've been the ghost as well.

When it feels like there's an unspoken agreement that something isn't going anywhere, it sometimes seems easier to just disappear, but the problem is that if an agreement is unspoken, it's not really an agreement. It's more of an assumption.

No Text Guy

I was on the wrong side of this in the fall when I dated a guy I'll call “No Text Guy” who was smart, funny, and handsome and we had what felt to me like fantastic chemistry. We both laughed a lot, told our stories in the proper ratio (no one person acted as Conversation Hijacker), and were definitely attracted to one another.

After two dates that lasted for hours, I made the mistake of going home with him. 

Here's why it may have been a mistake: speaking of unspoken agreements, there's a strange one that the majority of daters seem to have come to, and that's that the third date is the Sex Date. 

I have no idea how it happened, or when the UN Summit on Optimal First Intercourse Timing occurred, but it's a thing now. It's a terrible, illogical THING.

For men, it's not really an issue, but women need to be aware of it, because for some men, a woman's decision to sleep with him or not signals a flipped switch in their mind wherein:

Sex on the first date = whore
Sex on the second date = whore
Sex on the third date = marriage material!

Some strange magic apparently happens to us in the time between the second and third date that sucks all the whore blood from our bodies and re-animates us with the blood of Meredith Baxter-Birney.

Of course I don't want to be with a man who thinks this way, but the problem is, I believe some men do, but don't realize it. Their penis and degree in Post-Feminist Lit think women should be able to do whatever they want with their bodies, but some dark part of their brain that they never visit is playing episodes of Father Knows Best on a loop and wagging its finger at hussies.

In any case, since I'm terrible at game-playing and think the Third Date Sex Rule is garbage and that the people who ascribe to it are garbage people, I don't generally follow it, and definitely didn't with No Text Guy.

Did I sleep with him too soon for him to consider me serious dating material? (He didn't seem like that guy.) Was I terrible in bed? (Possible, but I've taken CLASSES, you guys.) Was he freaked out by the absorbed twin I have in my left thigh? (I don't actually have an absorbed twin, but I do have some cellulite I'm not proud of. That could've been it.)

For whatever reason, when he canceled our third date with a very vague explanation, I knew he'd lost interest. I pushed it well past my comfort zone (I have an irrationally strong fear of being that person pursuing someone who's not interested) and asked him out one more time, to which he acquiesced, but then he just stopped contacting me.

In that situation, where it felt like things were going so well, I would've loved/hated a quick note of explanation. It would've felt terrible to hear, “I just don't think the spark is there,” but it would've beat a couple weeks of wondering what the hell happened. 

That being said, it sort of served me right for the time I was the person not making that call. 

Dating Karma is also a thing.

Even though we'd only been on three dates, No Text Guy stung a bit more than the others because at that point, I was so tired. He'd been first date #26 and one of only about four men over the course of the year that I thought there might be a future with based on sparks that apparently only I saw. 

So in the winter, things slowed down to a crawl.

I continued seeing the polyamorous married guy I mentioned in an earlier column, and spent some time in November with a very sweet man whose smile sucked me in even though I could count the things we had in common on one finger. 

Date 28

First date #28 happened on the day after Christmas. 

It was lovely.

I'm still seeing him and not really thinking about where it's going, but also not thinking about who else I could be dating.

It's nice. And quiet. And I like that.

In all, last year I had 28 first dates, and 13 second and third dates—seven of which I ended up seeing for a couple months. 

I never set out to rack up some big number, I just kept responding to people I thought seemed interesting, and I was almost always right on some level. 

I do think I'm going to get off the treadmill of online dating for a while.

I understand the appeal of accessing a wide variety of people and actually be able to compare them to one another from night to night if you so choose, but after a year of it, I just don't think it's that effective.

Additionally, I'm a little concerned about how my psyche's been affected by the illusion of plenty that online dating creates.

Let’s be honest, the idea of a person is almost always better than the reality. When you go on a date with someone you met online, you carry with you the idea of literally thousands of people just waiting at home on a website you can access at any time. And because of that fact, you're a lot less likely to give the person you're with the chance he deserves.

I think there are long-term effects of this as well.

So does Dan Slater, who wrote a book called Love in the Time of Algorithms. In it, he said, “...three ingredients generally determine the strength of commitment: overall satisfaction with the relationship; the investment one has put into it, and the quality of perceived alternatives. Two of the three—satisfaction and quality of alternatives—could be directly affected by the larger mating pool that the Internet offers.”

So it's not just dating that this way of thinking affects, it's the relationships that result. 

My hope is that all this exhausting charm I've been mustering will ultimately result in a relationship. Maybe not now, but someday. 

And when it does, I hope the person I'm with is willing to stick with me when things get weird, like when I call him because I heard a strange noise outside and I just watched Human Centipede and sure the doctor from that movie lives in Germany, but he’s a doctor. You don’t think he has a passport?

When that happens, I hope he doesn't think of the twelve OKCupid ladies he’s still chatting with who don't appear nuts because he doesn’t know them yet, and bolt.
Because that would make me sob. In my car. Again.

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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