This Is Why Generation Y Fucking Hates Online Dating

I am Generation Y. Do not millennial me unless you’d like a kick in the teeth. I get that we’re ambiguous. Too young to be Gen X, too old to be Millennials. One article found on The Atlantic can even be quoted as saying, “Generation Y is a fake, made-up thing. Do not worry about it.” Dick.

I am generation Y. I was born in the very early 80s and if you need a unifying identifier that gathers us in unbreakable, non-millennial stature, here it is: We remember being teenagers without the internet, and we remember being teenagers, with it. We’re it, the cusp. The crest of the wave. The forgotten, early 80s-born, un-entitled children of technology’s greatest crossover.

We remember when MTV’s The Real World had purpose, when it respected itself. To us, Wayne’s World is more movie than SNL sketch. We recorded Pearl Jam onto cassette tapes when they came on the radio. We listened to the radio.

But we were not single in the 90s.

We were just kids. Most of our sexually formative years involved in-person activity, but don’t think we weren’t on the front lines of the first chatrooms in existence dabbling in what you now call sexting, apparently an entirely normal part of the current dating process even though you conveniently leave it out when you tell stories about the new guy you’re seeing to your companions at brunch.

There was no Tinder in the 90s. No smartphones, no face swiping apps allowing us to thumb through pictures of human beings like shirts on a clothing rack at Marshall’s. If you were old enough to be dating in the 90s, there were phone calls and answering machine messages and blind dates and a sense that if you met someone, you should ask them out, rather than settling into some sense of creepy comfort that you could stalk them on Instagram later.

That’s what we were watching. Those were the items written into television and movies being played out by older siblings and cousins. We figured we’d just meet someone the way they met people, because why in the hell would that ever change? It hadn’t changed before. At least not since the heyday of the matchmaking yenta.

I pity my generation. We learned about life in one way, and then had to go and live it in another.

Today’s teens, those just tiptoeing into the shallow end of attraction and romance, they know what a dating app is. They know that that’s how you meet someone to date. It will have never felt weird to them. Quite the opposite, that’s what will feel normal to them. A phone call from an admirer would make them soil their underwear from Target. I still remember getting looks of horror the first time I told someone I was trying “online dating.” They just assumed they’d read about me dead in a newspaper within the month.

It was gross back then. It was weird. It was desperate. “Why can’t you just meet someone the normal way?” Now, when someone finds out I’m single it’s always “why don’t you try online dating?” And isn’t that just the tits?

I am a living, breathing tipping point that was both shamed for online dating and encouraged to do it, all within the timespan of my singledom. Is this a joke?

“Shani, why do you save all this stuff?”

This is why.

I was forbidden to call boys. When I lived under my mother’s roof, I could not call a person with a penis. If one called me, fine. But I was not allowed. Boys were for older girls. They were not for me. They were a distraction. When of course they were all I thought about. Dating was always the thing you did “after you’ve got your career.” And this wasn’t a mild suggestion, it was a command. My mother was raised that girls get married, and she was determined not to raise her daughter the same way. I was raised knowing that girls get jobs. Naturally, a man you’d want to date doesn’t magically appear once “you’ve got your career,” he isn’t issued to you like a Christmas bonus, there’s no more likelihood you’ll find him then than you would have at 16, but Mom meant well.

The way I learned about boys was in what I would call the “normal” way. They way it has existed for all time until now. As children, teasing. As teens, awkward flirting usually preceded by friendship. In college, alcohol-fueled sex that gave us some illusion we knew what we were doing. All the ways I interacted with the opposite sex were in person. They were real. And then when I got my career, when it was time to go out and really use the wealth of knowledge I’d built up, the game changed entirely.

People stopped meeting in person. Suddenly we were all too “busy” to meet someone during the natural course of life that literally every couple since the dawn of time had used to meet their partners before us. Not us, no. We’re too busy. We’re special.

The internet is nothing if not a business opportunity, and someone decided to monetize love.

I signed up for my first online dating app in law school, in 2005. I’ve always been an early adopter of technology (late bloomer in literally every other way), but in reality online dating had existed for 10 years by then. was created in 1995. Sounds strange, doesn’t it? To think of online dating in the 90s. That’s how long it took for people to be okay with it. To not be horrified by it, for it to become the norm. I was still “weird” for setting up an online dating profile 10 years after the invention of online dating, but I was horribly late to the party when I waited two weeks to download Pokemon Go. That tells me a lot, the slowness of humanity to warm to online dating. It speaks to the unnatural nature of it. To its oddity.

Why would people do this? Why indeed.

But boys didn’t like me. They never really did. I spent the whole of the 90s watching girls in high school have “boyfriends” they “dated” for two weeks and then broke up with in some very intense way. But it never happened to me, I wasn’t a girl boys paid attention to, and it never bothered me because I was scared shitless of them anyway. This has been the general rule my entire life, the un-appeal of me. I just took this as truth, until law school, when I suddenly realized I was kind of a grown up, and this shit wasn’t going to fly anymore.

I didn’t know anyone else who was dating online. It felt icky. It felt like there was something wrong with me because I “had to” resort to online dating. This was still the general opinion of online dating at the time. No one in law school was truly interested in me (of course they weren’t), and I was watching other people connect with their future spouses left and right. And that isn’t an estimation. These people are married with kids now. They’re very happy, I know. I have Facebook.

Overall, I have spent a total of nine years online dating. Nine years trying every app, website, and method imaginable. I have never once, not once had a relationship result from this practice. Countless first dates. Fewer than 50 second dates, maybe a handful third dates, and plenty of one night stands as consolation prizes. But not one boyfriend. That is the fucking truth.

Poor suckers.

Odds alone, I should have had a boyfriend this way. I’ve been out in the ether for so many years how is it not possible that one man who wants me around for longer than a Tic Tac has found and pursued me? I’ve pursued plenty by the way, to absolutely no avail.

I do not suffer from self pity or doubt, I know I’m a love-worthy person. I am not terrible looking, I’m smart, moderately funny, and I know I’m kind. I try very hard at that. I can imagine that eventually someone might like to spend some time with me, I can see that as a realistic outcome. Conversely, my ego is not inflated. I know I have a lot to work on. Confidence-wise I hover somewhere in the middle to keep myself at a good pH balance.

So why then, no boyfriend? The confusion you might be feeling, the confusion I now have as a building block of my psyche, has been this cloud of mystery hanging over my late twenties and early thirties that exists, almost like a living, breathing thing in my day to day life, that no one can explain. That everyone thinks requires explanation, because I’m alone. Because nobody likes fruitless effort without some kind of cause or lesson learned. We’re programmed to get something for our money.

How is this not working? What does “working” even mean? I think it means meeting at least one person via online dating in nine years who wants to hold your hand. But I haven’t. I’m not entirely sure I’ve met that many hands I want to hold, either. But by now, by this time, shouldn’t I have had a little success, even by accident at this point? Why is this so hard for me?

You know the answer, just as I do.

I’m not good at this. This isn’t for me. This isn’t how I’m going to meet someone. It’s not the way.

And why is that surprising? The world groomed me, my entire youth, to meet a man as humans do. In life. Among friends. Comfortably. Genuinely. I learned that people enter circles of other people’s lives naturally, perhaps with Fate’s help, with the tides of life bring people together. It’s all I ever knew, because it was literally all that had ever happened before.

And then I started dating, and dating changed.

Everything changed. But everything I wanted stayed the same. I wanted to develop a friendship with someone before I dated them. I wanted to marry a best friend. I wanted to look back at how we met with fondness.

I like meeting people in person, but not just in person, over time. I like repeated exposure. I think it’s what allows attraction between two people to steep. Of all the lessons online dating has taught me, the most unignorable truth is that I don’t make a very good impression in two hours. I think you have to spend more time with me. You need to see how I am, see how I interact with people other than you. And you’re never going to get that if we meet for coffee or drinks or some other safe first meeting activity.

And that’s another thing. They’re not dates. First dates, if they result from online dating, are not dates. I’m a linguistics fan so let’s please call them what they are. They’re meetings. They’re two strangers saying hello for the first time. There is no romance there, there are no butterflies. He’s a total stranger I’ve texted with for 15 minutes. We do not know each other, and yet the premise of online dating is that in that first meeting we’re supposed to develop enough attraction to each other to want to see each other again. To want to make the effort to see each other again.

It won’t happen naturally, we’re not in friend circles where we’d see each other at a BBQ by accident a week later, as a pleasant surprise. No, we have to meet, spend a brief time conversing, and in that time develop enough interest on both sides of the table the one of us is going to make effort to ask the other out again, and that person is going to say yes.

Am I the only person who thinks online dating is illogically setting us up to fail? I mean am I?

What’s going to happen is that it’s going to fizzle out. Neither will put forth any effort toward a second meeting. “Yeah, he/she was nice I guess, but they didn’t ‘wow’ me, you know?” We’re all waiting to be wowed. Wowed! No pressure or anything, you’ve got two hours and two glasses of Sauvignon Blanc: Go!

What we ignore is that wow is an accumulation of moments over time. They don’t all hit at once. The internet has made everything instant, even our assumptions of how quickly we should be attracted to people. We’d take a slow-cooked boeuf bourguignon at a French restaurant over a microwaved burrito any day but the person we’re going to spend the rest of our lives with better convince us of their worth, instantly. Such logic. Such sense. Wow.

Can you imagine the strength of the lightning strike you’d need to meet a stranger for the very first time and actually begin to develop real feelings for them? Online dating is a giant pool of people, there are literally millions of individuals involved. Millions! Do we really think that “matching” with one of them carries any real potential for attraction? What does matching even mean? He looked good in his groomsman suit and I wore a very low cut dress in two of my pictures. There. You matched. Good luck you two, off you go.

And yes, we all know someone, or several someones, who met their spouses via online dating. Mazel tov to them and their families. But assuming that is the rule, rather than the exception, is ignorant. Yes, every now and then a couple will meet, fall in love, and marry as a result of online dating. But you’re not looking at the success rate. Millions of online daters and you know two couples. Two couples who got married that way. I know three. Your neighbor’s old roommate. A former colleague. Your cousin’s best friend. Good. Good for them. What about the millions of the rest of us?

The only real boyfriends I’ve ever had, and there aren’t many, I’ve met in person. Not only have I met them in person, but I haven’t lifted a finger. “He saw her from across the room…” that old chestnut, has proven true for me, every time. If a man is interested in me, he will make it clear, and if I am interested back, there will be a wonderful connection, a new person in my life. But these people are rare, few and light years between and I have to be patient. You could write “date me” in the dust of my patience right now.

I don’t think this works, online dating. Not for my generation. Not the generation that learned how to date in one way, and actually had to date in another.

It’s the cruelest bait and switch. And we’re the only generation it has happened to. We are Generation Y, the generation the world jilted.

Today’s teens will find it odd to meet their spouse at a birthday party at a friend’s apartment. The question won’t be “how did you meet,” but instead, “ which app did you use?” And I don’t scoff at that, I don’t see anything wrong with that. It’s what they’ve got. It’s what they’re learning. It’s what they’ll use. I don’t really foresee the internet ceasing to exist when the graduating class of 2026 begins to couple.

They might actually find it more comfortable to “stalk” someone’s Instagram from across the room at a party or event before they speak to them face-to-face. Because we’re comfortable doing what we’ve always done, what we’ve learned. We wouldn’t dare take away the phones of Generation Z just as they start to date, the poor things would be terrified. Yet there was no problem at all tossing Generation Y into the deep end of app dating without swimming lessons.

I’ve been robbed. I’ve been robbed of the dating future I was groomed to have. I thought dating was just that, dating. I thought that’s what people did, what I would do. I looked to the future and and journeyed in that general direction and then arrived someplace completely different. A Willy Wonka rowboat ride. And I’m angry. I didn’t learn this, I didn’t prepare for it, I’m learning as I go. And a 19-year-old learning these things and making her mistakes has a lot more time to make mistakes than someone who is 34.

On behalf of my generation’s single women, on this page, and on many others, allow me to say what we’re all thinking, what we’re all sick of participating in, failing at, slogging through. Allow me to clarify for anyone who doesn’t understand why some people don’t have success at online dating, as if that’s even something numbers and logic suggest we should have. Let me tell you why the people of the forgotten Generation Y aren’t natural, easy, thrilled participants in online dating.

This isn’t how we we were raised. This isn’t right for us.

This is bullshit. Thought Catalog Logo Mark

Shani Silver is a writer and editor living in Brooklyn, NY. Her work currently focuses on essays in the dating/single life/women’s lifestyle sphere, but she’ll complain about anything, really.

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