Fixing online dating

Online dating: a huge opportunity if you can make it work

Periodically I survey the internet landscape looking for business opportunities. In particular I look for online services that (a) don’t work very well and (b) can be fixed with better technology.

I haven’t found many. All the obvious online services work about as well as they possibly can. When it comes to search, retail, share trading, maps, video, music, and messaging it’s hard to see how they could be improved. Admittedly I missed the picture sharing niche – now filled by Instagram and Snapchat – but that’s probably because I’m not a teenager!

Online banking is an area where there’s a lot of room for improvement, but the constraint there isn’t technological – it’s mostly regulatory – and the barriers to entry are huge. Maybe Facebook or Google could launch a global banking service that disrupts the industry, but a start-up couldn’t.

No, the only niche I’ve found that fits my criteria is online dating. People spend enormous amounts of time on dating sites, filtering through a lot of noise, and occasionally going on dates with people who, by all accounts, may as well have been selected at random. Many people eventually give up in frustration.

So, what would an ideal dating site look like? Well, it would collect your details. It would analyze them using complex algorithms and match them against everyone else’s details. Then it would return a list of people who are the best you are going to get, and who are guaranteed to find you attractive. Simple! Although I’m not sure about the revenue model …

Why online dating doesn’t work

We’re a long way from achieving this ideal service – assuming such a thing is even possible – so let’s first figure out why the existing services don’t work.

To begin with, let’s assume that everyone can be assigned an attractiveness score from 1 to 10. If all men and all women stood in lines sorted by “attractiveness”, the top 10% would be assigned a 10, the next 10% a 9, and so on. All the tens would go out with tens, the fives with fives, and so on. There are some wrinkles when it comes to differences in age, education, and religion, but basically that’s how the real world works.

Ranking women by attractiveness is fairly straightforward because it’s all about looks. Anyone can do it, just using photos, and will come up with the same rankings, regardless of whether they’re male or female, gay or straight, and irrespective of culture. The ability seems to be hard-wired into the human brain, although interestingly it’s not something computers can do yet.

Where things get difficult is ranking men. Looks (especially height and muscle) count for a bit, but women also want to know whether they’re successful, confident, wealthy, considerate, funny, yada yada yada. You can’t tell those things from a photo, and probably not from a written profile either.

So how do you figure out a guy’s ranking? Well, I can think of three ways …

  1. Date him. This is time-consuming. If you believe the Pick Up Artist community it takes a woman 7 hours worth of dates to decide if a man is worth sleeping with. However, it is the gold standard, and a successful matchmaking algorithm may have to somehow replicate it.
  2. Self-selection. One person who knows a guy’s ranking is the guy himself, at least at an instinctive level. Men will usually only approach women of the same level of attractiveness. They won’t go much higher – rejection hurts – and they won’t go much lower – hey, they can do better. I suspect women know this intuitively, and are more likely to consider a guy who has the confidence to approach them.
  3. Look at the exes. There may be the odd aberration, but if a guy’s exes are mostly threes and fours, he’s probably a three or four. So be careful who you have your arm around in Facebook photos!

So why is this relevant? Well, consider how dating sites work. Men contact the women, guided by their looks, just like in the real world. But there’s no face-to-face rejection. There’s no downside to contacting someone out of your league, and a huge upside. So all the guys do it.

As a result, the attractive women get flooded with requests. But they have no way of sorting the good from the bad because there’s no way to evaluate a guy’s attractiveness. They may resort to some arbitrary selection criteria, but since personality is so important, the criteria are probably no better than a coin toss. So they end up going on dates with guys who are, on average, worse than the self-selected ones they meet face-to-face. Eventually they give up on the online world and go back to the bars, book clubs, or wherever it is that attractive women hang out.

Things aren’t great for the attractive men either. They have no way to stand out from the crowd and line up a date with the attractive women they usually hook up with, so they also give up and go back to the bars, etc. And with the attractive people all leaving, the site goes into a bit of death spiral, propped up only by an infusion of naive fresh meat.

Possible solutions

Let’s look at a few possible ways to improve things.

  • A first-principles matchmaking algorithm. I have no idea how this would work. Not only would it have to model a guy’s personality, it would have to model it when faced with a particular woman. This probably requires a full brain upload and lots of simulations, which is way beyond current technology.
  • Add rejection to online dating. It’s an effective feedback mechanism in the real world, so why not in the online world as well? Well, in the real world, a woman usually has enough information to quickly identify guys who are clearly not in her league and send them on their way. But in the online world she doesn’t, and the rejection signal wouldn’t be much better than random. Rats who receive random electric shocks tend to end up depressed and unhappy, so this is almost certainly a bad idea.
  • Include pictures of guys’ exes. In theory I think this would be a brilliant solution, especially if computers eventually get as good at ranking female beauty as people. But in practice there are serious privacy concerns – can you post pictures of exes without their consent? – and a strong incentive to game the system with selective pictures. But honestly, Facebook kind of works this way already, which is why people these days are more likely to exchange Facebook details than a phone number with someone they meet at a bar.

So I have to concede defeat here. I can’t figure out a service that works better than guys approaching women and saying hi. Maybe I should open a bar.



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