This one looked amazing.

I bookmarked her profile and fired the first shot:

“Bonjour ! I read your profile and think we might get along; want to grab coffee some time next week?”

No response. Wait one day. Second shot:

Perhaps I can tempt you with some pastries instead? I know of place with fruit tarts, chocolate pies, and macaroons. :)”

No response. Wait one day. Third attempt:

“Fine, if you don’t like coffee nor pastries, we can do tea. How does tea sound?”

Her:

“You’re confident, I like that. Tea sounds good :)”.

Bingo. But I wasn’t confident, I was automated.

Normal dating was a nightmare so I hacked it

I’m a fat, bald, short guy whose only quality is that he isn’t an ax murderer. I want to find the One, the special relationship that will last many years and multiply happiness. Relationships are multipliers of life experiences.

But I’m bad at small talk, and I jump too fast to intellectual conversations, making it awkward. Last year, my girlfriend and I broke up. The love wasn’t there anymore. Since I’m 31, and eventually want a family, I figured I’d better not procrastinate. I needed to be serious about dating.

So I downloaded Tinder and started swiping.

I decided to hack the system and go for volume instead of personalization. To hell with romance. I was determined to find the One, even if it meant swiping right the whole Bay Area.

For any serious endeavor, you need a serious process. I wanted to find the perfect match, so I wasn’t going to be an amateur about it. I needed to come up with a rigorous and scientific process. Luck exists, but it can also be forced.

You need a certain amount of candidates to be able to benchmark what quality means, and humans are really difficult to assess. In computer science, this is known as the optimal stopping algorithm, aka the secretary problem.

A few lines of code later, my app was born. An abstraction layer capable of managing online dating for me:

Automatic swiping

Automatic messaging

Automatic date scheduling

Sweet. Here’s what happened when I launched the program:

The app I made that automates the repetitive work in online dating.

I quickly got hundreds of matches, and hundreds of messages. It looked like this:

Tinder has the most liquidity.

My first problem was solved: getting leads into the pipeline. I had a new problem now: volume.

So I decided to industrialize the process.

Dating at scale to find the One

Go on as many dates as possible

I had to qualify each lead — see with which girl there was a fit and with which there wasn’t, to maximize chances of finding the One.

I automated everything. Openers, follow-up messages, swiping, bookmarking, text messages and phone number recording. The machine was well-oiled.

I assumed canned messages wouldn’t work well, but after over 10,000 sent, there wasn’t a significant response rate difference between personalized and generic messages. At least, that’s what the data said.

I became an online dating magician who knew how to optimize a profile — A/B testing pictures and message. If I changed my profile picture and got more “likes” as a result, that meant it was better. I was tracking data, which made it easy to see what performed best.

This one worked, probably because it hides the bulging stomach and the balding head.

This one worked, probably because it hides the bulging stomach and the balding head.

Conversion rates increased: more matches, more leads, more dates to schedule. A new match would receive up to 7 follow up messages to maximize response rates. To give you ballpark numbers, 43% responded after the first message, 21% after the second, 14% after the third, 9%, 3%,1%, 1%. The rest sent me a message first.

Here is the standard sequence of messages I used:

Bonjour ! Care to meet over coffee some time next week? Perhaps I can tempt you with some pastries instead? I know of place with fruit tarts, chocolate pies, and macaroons. :) Can I interest you in a chai latte then? Better than coffee, and we can still get the pastries! Fine, if you don’t like coffee nor pastries nor chai, we can do tea. How does tea sound? Yeah, you are right. Tea is a little boring. We should get ice cream! How about the Bi-Rite Creamery? Ice cream is too cliché anyway. We should do something no one else does on a first date, like meet at a gas station and get beef jerky! Think of the stories we could tell our grandkids! Alright, I’ll admit that meeting at a gas station isn’t the most romantic. And let’s be honest: American food portions are so large we don’t need more calories. How about a boat ride on Stow Lake? We can get a nice pedal boat and get fresh air and plenty of exercise. How about that?

As soon as it got an answer, the program would prompt for a phone number, leading sometimes to disjointed conversations.

The number would then be recorded in my custom CRM and automated texts would be sent with Twilio.

I also had some tricks — like subscribing to premium services to make my messages more visible. It worked well to get attention:

But not always interest:

I was now dating at scale, I could handle the influx of new leads. But my goal wasn’t to fuck around, I was here to find that special someone.

Volume created new problems

The excess of choice made me wary of missing out on my perfect match. Now, I wanted to meet them all. To make sure I wouldn’t miss out, I designed a rigorous first-date process.

Coffee only . It was cheaper and provided an exit for both participants. You know within the first 30 seconds whether it’s going to be a good fit.

. It was cheaper and provided an exit for both participants. You know within the first 30 seconds whether it’s going to be a good fit. Nearby location . I’d send an Uber when distance was an issue.

. I’d send an Uber when distance was an issue. Parallelized dates — up to three a day — to speed up process and increase time efficiency.

— up to three a day — to speed up process and increase time efficiency. After the date, I would write observations on a spreadsheet to avoid blunders. After asking “how’s your day” up to three times a day, I got confused. I once asked a girl who had spent the entire first date telling me a very sad story about her being an orphan. On our second date, I asked her how her parents were doing. That was an awkward moment. If you’re reading this, I apologize.

Yet I failed.

I failed at engineering love

150 dates without success

I went on 150 first dates but didn’t manage to find the One. Most of the first dates led to nothing: we didn’t have much in common. Dating at scale doesn’t go well with well fitting areas of interests.

Dating is like enterprise sales. When your customer goes for a competing, more compelling product, you’re never told and you don’t get any feedback.

You just don’t hear from them anymore. As such, you never know what you did wrong. As a founder, I stubbornly believe that everything is within my power to fix, and that something could have been done differently to force the decision in my favor.

On the rare occasions when I was genuinely interested in a date, she wouldn’t be. One decided to end things despite “having enjoyed her time with me, for what it’s worth”. Another was exceptionally caring, and made me feel special, valued. She too vanished. Some were bad luck. One had a tiger mom forbidding her. Another moved cross-country.

Then there was Her, let’s call her Jane. She was amazing. She worked at Google. She was fun. I had a special feeling so I brought her on a special date at the Golden Gate Park.

I brought a basket with fruits, macaroons and red wine and rented a boat. We took turns, and she rowed with the vigor of a thousand vikings. At some point, we got lost and I used this opportunity to steal a magical first kiss.

That was my best first date on more than 150, ironically the only one that hadn’t been part of my rigid routine. With her there was no doubt: I needed a second date. We went to a restaurant. Outside, she climbed on my shoulders and I ran uphill while she laughed. I might have fallen in love that day. We kissed again.

We went on a third, then 4th date. I wanted to tell her that I liked her, but I was anxious that she wouldn’t.

On our 5th date, she said she wasn’t ready for a relationship. I didn’t have the guts to ask why.

The strategy was flawed

Having more matches increased my odds of finding someone interesting, but it also became an addiction. The possibility of meeting that many people made me want to meet every one of them, to make sure I wouldn’t miss the One. In the process, I also found out something horrible:

I still believe technology can hack love, though that belief is likely irrational. Technology is leverage, and I think I leveraged it wrong: the execution was fine but the strategy wasn’t.

Perhaps a better strategy would hinge upon Mark Granovetter’s research. He argues that 2nd degree connections are the most useful: relationships and jobs are found through them. I should ask for intros!

Online dating does little in the way of encouraging you to put effort into a relationship. There’s always the allure of finding something better or just different. When you know someone in common, there’s a bit of reputation on the line so you behave differently.

Another issue is that culturally relationships are driven by men, at least in the first innings. This is different in the more progressive Scandinavian cultures. In my sample of 150, not once did a girl take the initiative, pick a place, and invite me. I’m told it’s fear of appearing desperate, but fuck that! Own your life, don’t let someone drive it for you.

I’m running out of steam. It is a very time, resource, and attention consuming thing. The whole point of automating was precisely to make it not so.

It’s time for another approach. A drastic change. But not tonight.

Tonight, I have a date.