Fifty First Dates

Please don’t confuse this post with the cute romantic comedy by the same name starring Adam Sandler and Drew Barrymore. This is nothing like that.

Based on my recent experience, there is very little that is cute or romantic about modern dating. At best, there’s comedy. At it’s worst, it reinforces the fear that all of the good ones are taken and the only options left are to:
A.) Settle for less than you really want, or
B.) Die alone.

Because that's how it feels sometimes.
Because that’s how it feels sometimes.

I gave online dating an unsuccessful try during the holiday season of 2014 before giving up completely (if you missed any of that, you can catch up here, here, and here). I resigned to “work on myself” over the winter (and actually did) while promising to revisit the issue in the spring. Eventually, spring rolled around and it was suggested by a paid professional that I take another stab at “putting myself out there.” I’d rather light myself on fire than do any of that, but fine. Let’s do this.

This time around, I signed up for OK Cupid (because I still refuse to pay for this nonsense). I created another profile where I try to sound interesting and genuine, all the while knowing that it all sounds like contrived garbage, and waited for the good times to begin. While online dating, one of my favorite things to do was to enjoy an adult beverage or herbal refreshment, put on some music, and browse through dating profiles. Sounds like a great evening in, doesn’t it? And it is. Very entertaining. But be warned: If you are less than 100% sober while perusing profiles, you might misinterpret a thing or two. You might like some people who really aren’t that likeable. You might find yourself laughing at things that aren’t really meant to be funny.

Case in point, a dude we’ll call Pete. I read Pete’s profile and immediately thought he was the funniest man I’d ever encountered. His profile was witty and ironic in all of the best ways possible. He joked about the government and society in a way that would have made John Stewart proud (and good God do I love that man). His profile pictures were kind of “meh.” There were three photos, none of them of great quality (come guys, we talked about this), and he looked like a completely different person in each one (to varying degrees of attractiveness). But I really liked this dude’s personality, or at least what I’d read so far. So with fingers crossed that he looked most like he did in picture number two, I sent him as message. I am nothing if not efficient so I didn’t mince words; I told him I thought he seemed like a cool guy that I’d have fun talking to and that we should do that sometime, maybe, if he’s into it.

He responded right away and after some back and forth, we made plans to meet for lunch that Friday. I showed up to our date dead sober (the way one probably should show up for a first date). He did not look like photo #2, and I was quite confident that I was not ever going to want his face anywhere near my face. But whatever, he was funny and cool. If nothing else, we’d have good conversations and crack some jokes. Or maybe not. As luck would have it, I was in for a big surprise: Pete’s not funny. Not even a little bit. Nope, I was just buzzed when I read his profile. Everything I read as sarcasm and irony was him being DEAD SERIOUS. So, turns out, Pete is intensely anti-government, takes himself super seriously, is angry with his father, and all of his interests and hobbies involve the word “experimental.” Beyond both being humans, we had just about nothing in common, so I kept it moving.


Next was Doug. Having learned my lesson after the Pete mishap, I made sure I reread his profile with a clear head before sending any messages.

Doug’s profile wasn’t terribly comedic, which is fine; I’m funny enough for the both of us. Sense of humor or lack thereof aside, he sounded like a really interesting guy: a sculptor who worked in landscape and traveled the world when he wasn’t working outside with his hands (uh, yes please). We exchanged a few messages (his grammar was impeccable), and once I felt like we’d have enough to talk about in person, I suggested a drink. He doesn’t drink. I actually enjoyed that fact and suggested that since the weather was going to be nice, that we meet up in the park near my place and talk. He was into that idea and even took it up a notch; he suggested we bring each other a little present—nothing of any real monetary value, just a small token of sorts. He thought it’d be a fun thing to do.

This dude sounded promising. As planned, we met in the park. He was super tall and had rode his bike there. Yes and yes. We grabbed a bench and immediately got down to the business of exchanging presents. He told me to close my eyes and hold out my hands. I told him to buy me dinner first. He didn’t laugh. Right. I did as I was told and in my hands he placed something small and extremely hot—it was a very small, very hot potato. Yes, as in the starchy vegetable. Ok…sure.

It was my turn to present a gift. Because he was the sculptor of fake rocks for highly manicured outdoor spaces, I gave him a rock I’d had since college that one of my friends had written a quote on. I thought it was cool and relevant. Based on his reaction, he did not agree. He was less than impressed and didn’t try to hide it. And it was kind of downhill from there. He talked a lot about some radical diet he subscribes to where you basically eat nothing except for maybe four blades of organic grass because everything else is poison and will kill you. He talked about his relationship with his dad and how it has ruined his life; you know, the usual first date stuff.

We briefly touched on the subject of travel and I asked him where he was planning to go next. He mentioned a small town in Mexico where apparently the Earth’s magnetic pull is really high. In the interest of making conversation (and because he wasn’t asking me any questions), I asked why that mattered, which was apparently the stupidest question he’d ever heard. “Um, why is that important? Uh, because magnets are vital to a healthy mental and physical balance and blood flow and blah blah blah.” Or something like that. I don’t know, I stopped listening. Perhaps needless to say, there wasn’t a second date with that barrel of laughs.

There were a few more first-date-duds along the way. The dude who showed up over twenty minutes late because he couldn’t find parking and didn’t want to pay for a lot. (Side note: I wish dudes would stop trying to drive everywhere in the city. Public transportation, People. Look into it.) Then there was the writer who clearly saw himself in Hemmingway’s image as he spent a good portion of the date mansplaining to me what it means to be a writer (yes, I mentioned that I also write and no, he did not ask me to tell him about that). After I felt like I had given the Internet a fair shot, I decided to once again shut it down.

online dating

Then there was a fix up or two. I went out with one gentleman at a mutual friend’s suggestion. Her heart was in the right place, but I’m not sure why she thought we’d be a good match because that dude hated me. No, seriously. That man was charmed by me in no way (I know, I couldn’t believe it either) and did not try to hide how much he would rather be doing anything else.

At first I thought maybe he was nervous so I made a point to lean in, smile, ask questions, you know, put him at ease. Nope. He just didn’t want to be there. If it had been another Internet mishap, I like to think I would have called it a night before finishing my first beer. But because it was a fix up, I wanted to keep an open mind; clearly my friend sees something in this fool that I don’t. Or maybe not. Who knows. At one point, I asked him about his job and he said, “I hate my life so much, I want to gauge my eyes out.” I tried to hang in there, waiting for some flash of what might make this dude worth the time. But after he made a snide and judgey comment about the fact that I’d taken an Uber to the bar, I figured I’d just cut my losses and head home.

I’ll be honest, that last one got me down a bit. NO, not because I was sad that this dude wasn’t going to be the one. And not because I took any of his shit personally (please, I’ve read enough self-help books to know it’s not me, it’s him). This was a frustration that all of the single ladies over 30 (which might as well be 100 in dating years) can relate to. The frustration that has you talking out loud in your living room to no one in particular: “Seriously? HOW MANY TIMES do I have to do this before you throw me a bone?” Or to echo Charlotte from Sex in the City: “I’ve been dating since I was I fifteen. I’m exhausted. Where is he?”

I took a step back to look at the situation. I was trying really hard, spending a lot of time and effort on “dating” and I wasn’t having any luck. Luck? Hell, I wasn’t even having fun. It all felt really stupid and like a giant waste of my time and energy. So, I decided to quit. Quit dating entirely. I’m done. Kind of. Well, not exactly. Let me explain.

Next week.

2 thoughts on “Fifty First Dates

  1. Love, loVE, LOVE, this! While my attempts at dating have provided hours of amusement and entertainment in the post mortem story telling to friends, it has been nothing less than disappointing. Lower expectations? Try throwing out all expectations or die alone (well maybe not alone, I could always become a crazy cat lady). Im quite certain I have screened out the entire Rochester population of single men, ages 30 to 50… to no avail.
    Well written Raina.

    1. Giiiiirl, I feel your pain. I think anyone single these days is intimately familiar with the disappointing pile of trash that is modern dating. BUT. Don’t give up. There are a few billion people walking around this planet there. So mathematically, there’s at least one somewhere with your name on it. You just haven’t bumped into him yet.

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