This is the story of a girl, a boy, and the website that came between them.

Many years ago now, I signed up for every online dating website I could find. I’ll spare you the list of excuses and protestations that I am actually capable of meeting girls in real life; all that matters is that I like to check out every website I can — because it’s my job, and because it’s interesting.

I once paid a little bit for what was, at the time, the best of the sites. To protect the icompeten– I mean, the innocent, I’ll just call this site www.meetsomeonenicetosettledownwith.com.

There’s a kind of paradox of profit in the online dating industry. To be a successfull company, you have to actually successfully connect people, which means they are no longer customers. Your customers are paying you — even if your site’s entirely ad-driven — to make them non-customers as quickly as possible. If there’s a clever way around this, I don’t know what it is.

Over the years, www.meetsomeonenicetosettledownwith.com got worse and worse. Although I initially paid for “credits” which could be used to send messages at any time, they converted to an exorbitant monthly fee system, and instituted a rigid caste system much like India had for centuries, with “Gold” (Desperate and loaded), “Silver” (Desperate or loaded, but not both), and “Standard” (Broke, sexually confused, deceased, or untouchable).

“Sorry,” I thought, “but if I get that desperate, or that loaded, I think I’ll take my fifty dollars a month and spend it trying to buy drinks for cute punk rock girls — you know, the kind that don’t sign up for online dating — down at the local pub.”

Then www.meetsomeonenicetosettledownwith.com lost a class action lawsuit from their users and were forced to award some members extra credits. Their site design went from clean and elegant to cluttered, messy, and downright bizarre. The current design would make Edward Tufte break out in hives.

And all this time I became more and more disinterested — with both www.meetsomeonenicetosettledownwith.com in particular, and with online dating in general. (Trying to buy drinks for the cute punk rock girls down at the local dive bar isn’t such a bad idea after all.)

Every so often I would get a message on one of the sites I’d signed up for years earlier, and I’d sign on, check it out, and usually just delete my account. But I could never bear to delete my www.meetsomeonenicetosettledownwith.com, partly because I was harboring a secret hope that they would get a clue and go back to the way they were, but mostly because I’m a stingy bastard and I still had what amounted to about seventeen dollars worth of credits left on the site.

Fast forward a few years, to a slow monday morning at work about three weeks ago. I log in to www.meetsomeonenicetosettledownwith.com. After recovering from the visual assault that is their landing page, I notice that I’ve got a few new “profile views.” I check out the one with a picture, and what do you know but my lowly standard-user status no longer allows me to look at pictures full-size, so about all I can tell about this girl is that she would probably look ok if she replaced F.D.R. on the dime, or Queen Elizabeth on the Canadian Penny. (I know you’re reading this, U.S. Department of the Treasury.)

And what does it say underneath her profile but “She sent you one message 6 days ago.” At this point, you’d like me to tell you that my heart was racing and my palms were sweating. And they were, because it meant I could possibly waste another ten minutes before having to actually do some work.

So off I go to my inbox, and there are no new messages there, until I notice that there’s one “filtered” message. Messages get “filtered” if the sender doesn’t match the recipient’s desired parameters. When I signed up back when I was about twenty-three, my desired parameters were something like “women between twenty-one and thirty” because I’m a total asshole and won’t date a girl seven years older than me.

The erstwhile filter had filtered this girl’s message because she was thirty-one. I’m thirty now, fast approaching the time when I buy a red mustang convertible and use it to take the twenty-one year old blonde that I met on www.meetsomeonenicetosettledownwith.com out jewelry shopping, the wind whipping through my comb-over. So, in an act of pure desperation, I turned off the “filter” and read the filtered message.

Now www.meetsomeonenicetosettledownwith.com had me by the balls. The email from the Dime-Worthy Thirty-One Year Old was funny, short, and friendly. In my folly, I thought that perhaps D.W.T.O.Y.O might be someone I would like to spend an awkward hour with in a local dive bar, trying to make it less obvious to the cute punk rock girls around us that the two of us had met on the internet. And it allowed me to waste yet another ten minutes on that fateful Monday morning.

Fast forward a few days. I cannot sleep, for I am fantasizing about D.W.T.O.Y.O. Actually, it’s a slow Thursday morning and I’m trying to procrastinate again. I log on to www.meetsomeonenicetosettledownwith.com and check her profile again. Now, it says “She sent you two messages, one today.” Heart racing, sweaty palms, click on “mail,” you know the drill.

There is no message. Aha! I check the filtered mail. Still no mail. My heart sinks; I will have to work. I log off, assuming that www.meetsomeonenicetosettledownwith.com is using a cache and my message will arrive shortly.

Fast forward a few more days, through a drug and sex filled weekend, or, actually just a weekend with some beer drinking and hanging out with married people, to another slow Monday. And, well, you know, my message still has not arrived. I can only imagine what it must have been like for the great lovers a hundred years ago, waiting for the postman and the carefully wrapped missive from their secret lover.

Now I’m pissed, and worried. Www.meetsomeonenicetosettledownwith.com has been telling me for a week that I’ve got new mail, and poor D.W.T.O.Y.O. is probably crying herself to sleep wondering why that guy wrote back once and then never again. What’s going through her head? I know how it works — she’s wondering if she said something wrong, if I think she’s ugly or fat, whether I’m actually gay, or just an asshole. And I’m getting paranoid too. Does www.meetsomeonenicetosettledownwith.com only let paying customers carry on conversations? Am I going to run into D.W.T.O.Y.O. in my local dive bar and will she throw her drink in my face when she figures out who I am? I never asked for this kind of threat when I signed up for this site.

So I write a message to tech support at www.meetsomeonenicetosettledownwith.com, explaining my pathetic situation.

Tech support comment forms are usually like black holes, ravenous pits of nothingness which suck, and suck anything in, but only radiate miniscule amounts of Hawking radiation-like cryptic stock answers back at you. The tech support form at www.meetsomeonenicetosettledownwith.com is no different.

Another week passes. Life carries on as usual; with one exception. I want to know why www.meetsomeonenicetosettledownwith.com is so broken. Why it is telling me that I’ve got a message that I can’t see? I already know why tech support probably doesn’t care — it’s one guy in a basement in Bangalore with Windows 98 and a bad case of acne. And I also want to know why the “log out” button jumps around the page when I try to click on it, but that’s a whole different story.

I log back in. I check my filtered and ordinary inboxes. I lob another asteroid of a question at the gaping maw of tech support’s singularity. And I go to write another message to D.W.T.O.Y.O. Something clever, I think. Something that says, “www.meetsomeonenicetosettledownwith.com doesn’t want us to be together forever, but please don’t throw your drink in my face if you ever see me at your local dive bar,” in a way that’s funny and non-threatening.

And then I see it.

It’s a small button, in a bank of buttons between the subject and the body. It says “All by D.W.T.O.Y.O.” “I wonder what that does,” I think, and I click it.

This is what makes a hacker different from average person. The average person thinks “I wonder what that does, but I better not click on it because it might be confusing or I might break something.” The hacker thinks, “I wonder what that does; Click.”

Click. I’m a hacker.

The button takes me to a list of two messages. A band was playing somewhere, and somewhere hearts were light. The elusive message was there, one click away.

Click. (Hacker, remember?)

System notice: The body of this message has been removed as this member appears to have been abusing our terms of service. By blocking this member’s message, we reduce the incentive for future abuse and thereby provide a better overall experience for our members – we apologize for any inconvenience

Great. D.W.T.O.Y.O. is a lowly spammer. I struggle with this difficult revelation. My great hopes for that uncomfortable beverage in the local dive bar are dashed.

But maybe, just maybe, www.meetsomeonenicetosettledownwith.com is wrong about D.W.T.O.Y.O. I decide to reply, once more, just in case, and because the urge to procrastinate is just that strong. Reply button. Click.

There, in the reply form, is the original message. The one that I’ve been trying to read for a week. I read it. It’s not spam. There’s nothing in it that could even be remotely considered spam. There’s no URL, no email, no phone number, no “personal information,” as is strictly forbidden by www.meetsomeonenicetosettledownwith.com’s terms of service. She’s actually kinda funny. And interesting. And she’d look cute on a dime.

(That’s right, this dating site forbids their users from exchanging “personal information” with each other. Like, say, romantic or sexual desires, fantasies, fetishes — or even hopes for the future — that kind of “personal” conversation is not allowed. Nice weather we’re having lately, huh?)

Mighty www.meetsomeonenicetosettledownwith.com has struck out. In fact, they’ve lost the whole game. Here’s how:

System notice:

What? Why is there a system notice taking the place of a message that I was obviously never meant to see, since the message was automatically and invisibly removed from my inbox?

The body of this message has been removed…

Wrong. The body of the message was *not* removed. It is still here. I was able to read it, and that means it’s still in your database, and it means that your “spam” blocker is only working on part of your website. It means you have a database full of real spam. And that means that eventually, real spammers might find a way around your spam blocking.

…as this member appears to have been abusing our terms of service.

Wrong. I read the message. It’s not spam.

By blocking this member’s message, we reduce the incentive for future abuse…

Wrong. The site provides no feedback whatsoever to the sender when a message is spam blocked. Real spammers have no reason to think that their spam is not getting to its desired targets. The only thing that’s reduced is the end result for the spammers. But since real spammers (i.e., people other than poor D.W.T.O.Y.O.) have automated programs that spam hundreds of sites at a time, they probably don’t even notice that spam to www.meetsomeonenicetosettledownwith.com doesn’t work so good.

…and thereby provide a better overall experience for our members …

Wrong. You are providing a worse overall experience. Let’s review. There is no feedback to the sender when his or her message is blocked. This means, from the point of view of the sender, some messages never get responses. It is harder for message senders to meet people. And there is no feedback to the recipient when he or she receives mail that is spam blocked. There is no “Spam” folder, and no way to turn www.meetsomeonenicetosettledownwith.com’s broken spam filter off. So, from a recipient’s point of view, the messages don’t even exist (unless they are hackers). So it’s harder for message recipients to meet people too.

– we apologize for any inconvenience

What? If you truly believe you are providing a better overall experience for your members, why would you feel the need to apologize for any inconvenience? “Hi, we don’t suck. Sorry.”

P.S. Guys, you forgot the last period on your “System message:”. Just sayin’.

There’s a few important software design guidelines being violated here. When you have a complex, unpredictable, pseudo-intelligent system (like a spam blocker) you can’t give it full control and make it completely invisible, unless it’s always 100% right. 99.9999% isn’t good enough. If Amazon gave its recommendation system full control of the site, and would only let you search and buy books that were recommended based on books you’d bought before, they’d fold. Gmail’s spam blocker is almost always right, but they’re not so stupid as to hide the spam folder from their users. Pseudo-intelligent systems can’t be given full control unless they’re perfect; in other words, never.

And, when checking to see whether something is allowed or not, there’s always a bottleneck — a single point where that thing must always pass — and that’s where you put your check. UNIX doesn’t check file permissions in every program that opens, moves and renames files — it does it in the kernel, because everything — even things the programmers didn’t think about when they were designing it thirty years ago — goes through the kernel. You don’t check if a message is spam when showing the inbox, and again when showing the body of the message (which shouldn’t be possible but is), but not when showing the reply form or when showing the total messages sent on a person’s profile or when showing all messages from that person — because it’s confusing to the user, because it duplicates work, and because it leaves holes that can be exploited, by the procrastinating stingy bastard who won’t delete his account, or by the evil spammer who wants to transfer a bajillion Nigerian dollars into your bank account because you are so trustworthy.

But back to the story about me, Miss Dime-Worthy USA 2007, and www.meetsomeonenicetosettledownwith.com.

Tech support eventually emitted the following tidbits of Hawking radiation in my direction: “Bug #37666,” “PWSID: 240027_14234,” “LEVEL: 100,” and a platitude about how they’re going to look into the matter as soon as possible. And to be honest, I’d rather they forgot about it. I’m not going to tell them about the hole in their spam-blocker, because it’s the only way I can bypass it.

And I don’t trust them to fix any of this properly, not least because it’s not really in their interest to do so. The paradox of profit in online dating takes care of that.

To date, D.W.T.O.Y.O. has not written me back. I haven’t deleted my www.meetsomeonenicetosettledownwith.com account. Yet. I still have hopes that my last message might have escaped their spam-Nazis. I’m not holding my breath. Miss D, this is my final goodbye to you. It’s not you, babe. It’s not me, either. It’s the goddamn website — there’s just not enough room in this relationship for the three of us.

Hmm. It’s still early. I wonder if there are any cute punk-rock girls down at the local dive bar.