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The UX of online dating sites: Why You’re Meant To Fail


Photo of teddy bear staring at another bear on a computer

I’ve been trying to explain to friends for a while why the design of today’s online dating apps don’t work to find them the love they seek. Depending on what you’re looking for, online dating can open a wealth of opportunities and possibilities that your neighborhood simply can’t compete with. One of the things we don’t ask ourselves anymore is whether this bounty of access is really good for us.


Older online dating sites like OkCupid and Match were designed to give you access to anybody on the site if you’re willing to search (or maybe pay a fee to filter even more.) In these scenarios, you’re able to mine through lots of faces for a chance at a possible date.

While this setup surely comes with its own set of problems, using this setup gives a person searching the ability to find a potentially plausible amount of people who might be interested in dating them.

Going back to Craiglist before it became overrun with spam, was also a surprisingly rich place in big cities for discovering people you might never meet. It didn’t usually come with the biases that other networks had, so if you had a good conversation with someone, coordinating a meetup wasn’t that difficult. During one summer in Boston, I used Craiglist to find an apartment (when I was in Illinois), I bought a computer on there, a bed AND managed to find pretty much all of my friends from that summer on the network too.

Part of that might have been my approach — I wasn’t looking for anything romantic — but I think it had more to do with timing and the market.


I think the trick to online dating when you’re not meeting what the ‘market ideal’ is for your particular area is finding the fissures in the market. I know all of this language sounds so much like financial dealing, but you have to think like an economist when it comes to online dating if you’re going to maximize your time.

Or you can just hope to get lucky like a person who wins the lottery.

What do I mean by market inefficiencies? Understand what the market is looking for (probably not you) and then figuring out what things your market is looking for. The thing is, you don’t have to appeal to everybody. You just have to figure out how to align what you’re looking for, with your potential market. If you appeal to people who are always really tall, but what you really want is a short dude, then perhaps you need to target short dudes or indicate on your profile that’s a preference.

If there are other things you like or that are dealbreakers, you probably should state them. The problem is, most people can’t actually say what they don’t want publicly because it might make them look bad. Nobody wants to think of themselves as exclusionary, but we all do it and we always have our reasons.

The problem is when you use today’s set of dating apps, you’re only being fed in a limited way which deliberately means to waste your time to get you to reengage with the app. So when the app does a terrible job of matching you or your latest relationship flames out because the design of the tool wasn’t really aimed at enabling you to filter out what you probably needed to know ahead of time; then you’re back where you started and your trusty friend — badly designed app — is there to help you in your quest.


Tinder and its ilk — Bumble and others — do not have a primary job of helping you find love. Sure, it’s just mathematics that people will find something on the site. Or they’ll be like people who eventually stop looking for jobs when they are chronically unemployed and just never come back to the app.

The problems with the apps aren’t that you can meet people. The issue is the lack of information you get in order to make informed decisions about what you ought to be doing. Maybe you’re thinking, “that’s not the app’s job?” But here’s the problem: You sign an artificial contract when you start online dating when you decide that this tool will likely help you meet people you might otherwise not meet. Maybe all of your friends are married. Perhaps you’re only living in a town because of work or grad school. This happens a lot of in my college town, so I run into a lot of people who talk about their dating woes and the challenges of dating in a relatively small insular place.

Here’s what funny. In a town of 80,000 or so, I don’t really think of that as being that small. I’ve lived in a county in Wyoming that was the size of a state but had less than 20,000 people and so that’s small. And even in those places, people still use these flawed, badly designed tools in the hopes of striking luck.

It’s not really sad, it’s just poorly designed and apt to failure.

No dating app can parse someone’s intentions. If you sign up for a dating site in a moment of weakness, it could because you want company, someone to hook up with or perhaps you’re just looking to see who is out there. It’s impossible to really know what someone is thinking until you get in front of them. Even then, we all know our ideas change. For some of us, those ideas change daily, but I digress.

The real issue here is that the design of dating apps create false positives. It appeals to us to focus mostly on carnal reasons or some other affinity to help us make decisions. You can obviously meet people on smaller, more niche focused dating sites too. Those situations are great for exploiting market inefficiencies because the problem with sites like Tinder is that they’re not really designed for depth. Most dating advice sites you run into encourage you NOT to write an especially long profile on a site like that. Just highlight your best photos, write something pithy and start swiping.

I know that having a shopping cart of seemingly limitless people to date feels appealing. And for some personalities it can work. But honestly, if you’re a person on the fringes it’s just going to steer you towards 1) a lot of heartbreak or 2) false positives that seem okay but don’t really capture what you’re after.

Online dating is good/fine if you just want dating practice, because it’ll give you that. Too often, people go searching online for things they’re looking for because it’s a lot easier than the real life experience of meeting people. If you’re an introvert, it’s alluring to feel like you can still meet people — exciting and complicated — without having to get out of bed and put on pants. It’s just too many of us use online dating without an iota of understanding of what our actual goals are.

For instance, if you’re looking for a significant other, it would stand to reason that you should figure out what type of person you’re looking for in that regard and find someone who also wants some of things you’re looking for in a partner. You can’t really have deep conversations with someone early on about how they feel about finances, whether they want kids or whether they’re someone you’ll want to spend lots of time with in the future, because these seem like largely off-limits conversations early in a relationship. But if you’re after those things, then it makes sense to position yourself towards figuring those things out.

Since it’s against the rules to do this, we placate ourselves with cute dates and let our intuition guide us towards the joys of basic things. We read into stuff that isn’t significant and we ignore the stuff that is. We tell ourselves it’s great “right now” and hope the people around us can see what we’re doing and what’s good about it. All the while, we waste time and keep ourselves from the sorts of things — and people — we ought to be meeting or the types of interesting things we could be doing.

In other words, we start configuring our lives around dating as if “dating” is a real-life activity, rather than participating in actual activities.

Online dating doesn’t care about what you want. It just wants you to keep spending money finding “bae” and perhaps, share with your friends so that you can help them be less lonely too. What happens if you graduate college, move to a new town and don’t have lots of good friends nearby to vet whoever it is you’re going to bed down with? Perhaps you can trust your own instincts, but my experiences make me think that’s the opposite of what you ought to be doing.

How online dating could work better

So what would make apps work better?

1. Fewer choices. More constraints.

People are just not good at picking what they need, they pick what they want. Now you can get lucky if someone who you wouldn’t pick normally piques your interest and convinces you to go a different way, but many of us are too stubborn and/or set in our ways for that. So we pursue what pursues us back. Seems like common sense, the problem is, online dating starts with a flawed premise — it presumes that we know what’s best for ourselves.

Online dating in an ideal state would match you better with people you wouldn’t normally consider, who’d be a good fit for you. Which is problem according to philosopher Alain de Botton, because what you want is probably wrong.

2. Not designed for everywhere
Dating sites were built by city people and enveloping city geography. What would a dating site built by people who drive two hours to the nearest major city look like? What kinds of questions would that site ask and how would it attempt to mitigate some of the issues that people living in far-flung locales face with trying to meet new people and perhaps invest in relationships? I bet you can envision an entirely different site.

3.. Online dating induces you to invest too much, too soon.
In my own research, I’ve seen that people are either wildly self-deprecating or super casual about what they’re offering up. You just want to “hang out” and simulate the bar room experience of getting to know somebody in as realistic conditions as possible. The problem is, we’re probably wasting our time triggering false positives because at the end of the day, the mystery of meeting someone new will override any of the reasons we ought to stop.

It’s less that online dating doesn’t work, it’s just an inefficient way to find love.

You’re a lot more likely to self-select someone who isn’t as good for you as a long-term partner than if you rely on human intuition, real-life interactions and chemistry. There’s a reason that you don’t read many love stories about people using telegraph machines to coordinate long-distance love. It’s because it would’ve too expensive and time-consuming to take those kinds of risks, given how unlikely it would’ve been to work out.

We discount how many people show up on our radars daily that we don’t acknowledge, engage with or find out more about. It’s less about every person being a potential beau, it’s more that we close off potential opportunities and networks, because many of us are so rigid about the ways we conduct our lives. Then we complain about the lack of opportunities and retreat to a tool meant to lull us into a false sense of security — as if what we want is just a person away.

It’s all backwards and we can do better.

Also published on Medium.