How Many Maybes Do Single People Pay For?

Dating is an industry feeding on the fear, shame, and insecurity of singlehood—and it’s thriving.

How much would you spend to maybe get what you paid for? Personally, if I’ve made the choice to spend my money with a business or a service, I’m getting what I paid for, or they’re not getting my business. But in the dating world, it doesn’t work that way. Single people pay endless sums of money to various players in the dating industry. That’s what it is by the way—dating and “finding love” have become an industry, one that feeds on the shame, fear, and insecurity that single people adopt as a result of living life in a society that sees us as less-than and incomplete. The mere fact that the dating industry has grown to such a massive presence in the world constantly reiterates to us how important it is to “fix” our singlehood. It’s an industry that tells us we’re wrong for being single, takes our money, and is allowed to leave us single afterward. Y’all, that’s fucked up.

Six days ago, Bumble raised 2.15 billion dollars in an IPO. Billion. And at no time during the process of going public did Bumble have to report on how many happy couples are currently together due directly to its services in order to reach that valuation. That’s because dating apps don’t sell relationships. They sell the possibility of relationships. Just like casinos sell the possibility of wining money. You pay for the game, you don’t pay to win it. And in this way, the dating industry can take your money and it never has to give you anything more than a maybe. It feeds off our fear and shame, and hinges (pun intended) our hopes on one-off success stories that divert our focus from the fact that “success” isn’t what’s happening to us. Only a punishing, belittling, and often disgusting dating culture is happening to us. And we keep making it richer.

While I’m at it, Bumble’s CEO just made 2.15 billion dollars on an app that actually makes things easier for single men who can just kick back and let the women come to them, rather than creating an environment where responsibility is equal and consequences for bad behavior are real. How many of it’s 22 million users are actually finding what they’re looking for, without enduring emotional trauma along the way? But hey, female founder girl power, right?

I don’t like single people being taken advantage of. I also don’t like an entire cohort of people being groomed to believe that an (expensive!) industry full of “horror” stories is our only way out of singlehood. (I don’t believe singlehood is something that we need a way out of in order to stop being ashamed of ourselves, but you can read about that on your own time.) For now, I just want the people preying on those who don’t have romantic love, something that’s been societally exalted to gargantuan proportions, to stop taking our money.

So below, four key players in the dating industry that are selling you nothing more than maybes. Keep giving them your money if you wish, just be really clear on what you’re paying for, and make sure you’re comfortable with that.


A personal anecdote: My mother once threatened to post on my Facebook page that she was looking for a matchmaker for me if I didn’t find and go to one myself. This was back when I lived a life of single shame and also allowed my mother to invade my boundaries and control my behavior. I’m happy to report that neither are true today.

I found a matchmaker, went to visit her, let her tick boxes off on a clipboard during our 30 minute conversation, and then email me half a day later to let me know she’d take me on as a client if I gave her $10,000. For that money, she could guarantee me six dates. Six dates, not husbands, dates. For ten grand.

It’s an ancient industry, one that I know has led to many, many couples and families. This service also varies wildly in pricing and services. Use a matchmaker if you want, just make sure you’re comfortable with this kind of maybe. I was not. Nor, thankfully, was my mother.

Dating Apps

I got into some of this above, so I’m going to keep this one brief. How much money, over how many years, have you given to dating apps? Forgive yourself for all of it. For every penny. These are businesses meticulously engineered to repeatedly relieve you of your cash without having to guarantee you a damn thing. We all get a little brainwashed now and then, it’s okay. Just know that you’re allowed to stop using dating apps, which is the very last thing these money-making maybe farms ever want you to do. It’s not “lowering your chances” if they never once delivered on any of the chances or dollars you gave them.

And if you found your partner on a dating app, mazel. I’m not talking to you right now, go sit down. I’m talking to those of us who have spent years alone, have tried (and paid for!) everything under the sun, and yet find ourselves single and frustrated. Again, I don’t see single as a negative, but I’m speaking to those who do, because that was me for an entire decade and I see you. It can get much better, I promise.

Dating Advice Books, Blogs, Newsletters

There are countless methods, tips, tricks, and other suggestions that love to make single people think that luck, fate, and the freedom to just live our lives and meet people without spending money are romantic fantasies that never come true. (Sugar, I used dating apps for a decade and never had one relationship result from them, so who’s sellin’ a fantasy, I ask you?)

They’re doing a few things here:

1 — They’re reiterating the assumption that singlehood is a bad, shameful thing. If their “cure” exists, by default your “problem” must exist, too. We internalize this wrongness to the detriment of our self esteem.

2 — They’re trying to sell you on methods for dating that never, at any time, have to find you partnership—it’s just a maybe. Authors will often use their own married status as “proof” that their methods “work,” even if they met their partner organically. In terms of maybes, these are the cheapest, but I despise them all the same.

3 — Most importantly, they’re selling you the idea that something is wrong with you, and that if you just fix it their way, that’s when you’ll find someone. If you don’t find someone, they get to blame you, not their “methods,” which I find really fucking convenient.

Dating Coaches

Lord, okay. It’s much the same as dating advice books and the like. In some ways, dating coaches are doing something great. If someone is having trouble with social anxiety, confidence, or something else they need help to work through, great, I’m glad they’re not going at it alone and in no way do I think single people should go through everything alone. I’m a huge proponent of singles finding community, friendship, and support at every opportunity. Licensed therapists are also a wonderful resource here.

Where the maybe of dating coaching comes in is that none of them can tell you where and when to meet your partner. They’re not psychic. They can give you all the tips and tricks you want, but at the end of the day if an actual human partner is what you want, they are not selling it. They are selling something different. Again, be clear on what you’re paying for, and make sure you’re comfortable with what you’re actually getting from these people. Make them tell you.

It’s not that I don’t want these businesses to exist. It’s that I want them to be honest. I want them to be respectful. I want there to be consequences involved when single people feel worse for having used them. Peddling the potential of love to a cohort of people who don’t have it, and who are further shamed and belittled by society for not having it, isn’t an honest industry to me. But it’s a thriving one nonetheless, until we decide that we deserve so much more than maybes.


Shani Silver is a humor essayist and podcaster. You can read all her Medium essays here.

NPR once called me a humor essayist, let’s go with that. Host of A Single Serving Podcast. shanisilver[at]gmail

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