The misadventures of online dating

Yeah, it’s time to talk about this subject. Because, reasons…

Despite the tongue-in-cheek, lighthearted title and choice of opening picture, this, at least for me, isn’t going to be much of a fun article. It’s more like, unprocessed thoughts and experiences that need to be excised from my brain through the writing process. This is really for my benefit, but if what I expound to you here helps you avoid some of the same pitfalls I’ve made, well, then that’s something.

Dating fucking sucks. There’s no point in being recondite about my feelings on this. It’s a game that I don’t believe for a second that anyone wants to play, there are no rules because everyone has different interests, attractions, and pet peeves, and because of the invention of lying the whole thing is wont to blow up in your face at any given second.

Do I sound enough like a jaded cuss yet? No? Shall I elucidate further?

I would really appreciate a scenario in which two people who are attracted to one another cut through the bullshit and say: “you appear to be a prime match for my genetic configuration, temperament, and goals in life. Shall we exercise whether or not our compatibility has any merit?” No flirting, no trying to decipher “clues” and “signals” as though I’m Batman or Sherlock fucking Holmes, no creating openings that can come across as creepy or ill-favored, just get to the damn point. And if your response to this paragraph is “well that stuff is half the fun” then we’re not likely to be going on a date anytime soon, you grok?

Of course, I named this article “online” dating, so I ought to hone my sights in on that particular variant of this awful social torture device. Yes. Because for introverts who don’t have much of a social life, and don’t want much of a social life, the internet is oft where we find ourselves stumbling around, hoping to amble onto someone who we’d like very much to adopt us and take us home. Aside from my first girlfriend, who I once worked with and decided very much she wanted to date me even after our hilariously over-the-top disagreements in the workplace, my romantic entanglements have been initiated through the internet.

I’ve met some interesting people online. Some of them I still consider friends or acquaintances at least, to this day. More specifically, I encountered women who I think would be kickass friends to have, but adding dating or sex to the mix fracked everything up. Then me, being easily confused, sensitive, and inexperienced in dealing with people in general much less a woman I fancy romantically, I had a most labored time understanding why some women found that she and I dating would have an incongruent outcome. I took some rejections or changes of heart harder than I should have.

But, this is where it gets fun (not really). When you’re perusing the internet’s collective lonely hearts clubs (from the lowest of lows, such as free ads on sites like craigslist, to paid, professional-looking dating and match sites), it’s easy to allow your own loneliness and heartbreak to steer the hands typing at the keys and pointing the mouse. Because it’s so easy, because the online world allows people to put forth their best and hide their worst, because the decisions you make when sitting alone at home, half-drunk and lonely are different from the ones you make when you’re out in the wild, I’ve allowed myself to get involved with the company of those I ought rightly to never have even contacted. That’s not for a moment meant to say that I think I’m better than these people, or that they’re somehow beneath me as human beings, after all, we found each other on the same online channel and are presumably in the same state of life. However, what I do mean to say is that it’s easy, way more easy than you think when your heart is broken and you would just like to have a little bit of a real human connection again, to get involved with someone you really shouldn’t. Maybe there was one thing about them that I found attractive, and I fixated on that, causing me to overlook the other things I really didn’t care for. Maybe I didn’t even think they were attractive but we had a lot in common. Maybe the idea of a “friend with benefits” sounded really good (word of experience: that shit doesn’t work in most cases) when I was knackered on beer and playing Gears of War in my small clothes because it’s always too bloody hot where I live (I am going off on a tangent, I recognize this, don’t judge me). Maybe a lady fancied a certain type of relationship and set of sexual kinks that I thought was fascinating, but then I realized I am more interested in studying that kind of stuff as a writer and not as someone who would like to play it out for real (whoops).

I’ve responded to ads so ridiculous that I played along to see how absurd it all could get. In earlier days I was taken in by bots and/or trolls, who in short order try to get you to sign up for a pay site or finagle some way of asking you for money, and I wonder how many stupid, naive young men get taken in by that shit in desperation to either not be lonely or to get someone to play with their reproductive rod (someone who isn’t them). Fortunately even then I was possessed of enough fortitude to never part ways with money, just so I could ask bots out on dates or see a lady flash her naughty bits for a few seconds.

That being said, whether it was me responding to something that I figured in all likelihood wasn’t real, or writing a message to someone on a passably legitimate dating site, there are things I’ve written that make me cringe to think back on. Times where I engaged in satanic dark rituals like small talk, or maybe came across as a creeper or a desperate oddball make me shudder. What the hell was I thinking? I either wasn’t actually that interested but was some combination of bored/lonely, or I was so intimidated by how attractive the woman was that my communication skills dropped to below that of a child. Then on the flip side of that coin, I’ve put together paragraphs that I considered minor works of art: literate, charming, playful yet serious, personalized greetings or displays of interest to a lovely lady who I fancied, where I took the time to read what she wrote about herself, where I found out what we have in common, and tried to start a conversation that didn’t revolve around sex or telling her how attractive she is. The end result of this? Silence. Or the equivalent of: “that’s nice.”


Try repeating this cycle for year after year, punctuated temporarily by relationships that fail based on mutually agreed upon circumstances, or because your prospective mate decides to fire a hand cannon at your heart from point blank range.

Welcome to my world! Enjoy your stay.

I won’t spend the entirety of this post or my day taking a proverbial dump on online dating. I know friends who met their spouses because of an initial online connection. I know that for awkward people like me, sometimes the digital world is the best, safest way to meet someone, because, seriously, trying to find a mate at a bar or club?


Unless phrases like this^ are to be thrown around, I don’t think there is any chance of love or romance being found for me at the places where you humans tend to congregate in highest numbers.

And, may I have a moment to expound upon what a guy like me goes through in trying to date?

Women have it way harder then men in this world, let me be clear. And as a man, I have no way of truly comprehending what kind of shit women go through in merely living their day to day lives in peace, much less in finding a partner. The general awfulness of the male gender does create barriers that ought not to exist. Women should never have to feel uneasy around men, whether at work, in public, on an elevator, trying to walk home, at a bar, wherever and whenever. It sucks. And because I am conscious of this, and I know and have seen first hand how little respect the average man has for women, their privacy and their personal space, it puts me, someone who is already awkward, self-conscious, and intensely respectful of others’ privacy (because I want mine respected in return), in quite a bind. I’ve learned things through experience (for example, coming to grips with the fact that, if someone breaks up with you, even if you were going to be married, any rights or privileges you had to their time, heart, et al., are absolutely revoked unless they say otherwise) that make me feel wary of getting involved with someone again, because of how easily and how quickly an intimate relationship can be dissolved. Ghosting, or giving up on people at the first sign conflict or difficulty, is rampant and made easier and more seductive due to the rapidity with which one can find an easy date or hookup. Yet, you have to respect those boundaries, because without them you turn into a stalker, someone to avoid or have a restraining order placed against. Without observing limitations, you become yet another guy on a massive list of assholes that doesn’t understand the word no, or who thinks it’s okay to try to impose his will on a woman, or make her life harder.

When I didn’t understand why my fiance left, and almost allowed the heartbreak and depression to literally kill me, there might have been moments where it would have been proper to call me an asshole, to say that it is better to let go completely no matter how much it hurts, instead of trying to keep hold of a rope coming apart and down to a thread. Even if the way she ended it was cruel and heartless, her choice was her own, and none but her have a right to say where her mind, heart, and body ought to be. Had I been able to see past my own grief long enough to recognize this, perhaps less damage might have been done. Perhaps she and I could have been friends again someday. Alas, not. Even though I never stopped loving her, there was nothing romantic about not letting go. There was no grace or dignity in me trying to say or show that I cared after we fought and said things to each other that I didn’t, and I doubt that she, really meant, yet, we live in a culture that somehow glorifies the desperate man, don’t we? How many romantic movies paint the lovestricken and forlorn man as a hero when he is told “no” by a woman, only to go on some mad, elaborate quest to win her affection? Desperate stalkers who follow women around, write them poems, throw rocks at their window, or by some other means interject themselves into their lives, are lauded in our stories. Why?

“No” fucking means no.

And this truth is what I must confront as I flounder in the online dating world, a world that as time goes on is increasingly vapid, that is all about shallow attraction in a “swipe left, swipe right” culture. It’s all about feeding knee jerk reaction, short attention spans, and first impressions that don’t give accurate representations of the real person behind the profile. This leads someone like me down a series of misadventures involving awkward conversations, dates that I had no business going on, or the soul-crushing reality of being in my early thirties and having spent the last decade either alone or struggling to hold onto whatever modicum of happiness I could find. Now if I date someone my age there is a high probability that I have to contend with children and/or previous marriages. That isn’t meant for one second as a slight against a woman who is a single mother or a divorcee, but it is a reality of what I have to take on, when really even dating someone who is relatively baggage-free is still a monumental undertaking for me. Writing three novels was a cakewalk compared to this shit.

I offer you to consider this the next time you plan to swipe in one direction or the other, dear reader.


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