How I Went on 150 Dates in 4 Months Looking for 'The One'
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. But I'm bad at small talk, and make things awkward by jumping too fast into intellectual conversations. 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 needed to play my odds even if it meant right-swiping the whole Bay Area.
You need a certain number 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 date scheduling
I quickly got hundreds of matches, and hundreds of messages.
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"
I had to qualify each lead — see with which girl there was a fit and with which there wasn't, to maximize my chances. So, 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 sending more than 10,000 I discovered 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 with A/B picture-testing and messages. 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.
Conversion rates increased: more matches, more leads, more dates to schedule. A new match would receive up to seven 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.
A) Coffee only. It's cheap, and provides an exit for both participants. You know within the first 30 seconds whether it's going to be a good fit.
B) Nearby location. I'd send an Uber when distance was an issue.
C) Parallelized dates -- 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. It was easy to get confused. One woman 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. Awkward moment. If you're reading this, I apologize.
I failed at engineering love
Most of the first dates led to nothing: We did'’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. 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. Some were bad luck. One had a tiger mom forbidding her. Another moved cross-country.
My best match necessitated breaking out of the algorithm
Then, I found someone. 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 fourth date. I wanted to tell her that I liked her, but I was scared. On our fifth date, she said she wasn't ready for a relationship. I didn't have the guts to ask why.
My 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.
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 second-degree connections are the most useful for finding relationships and jobs. 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.
This story originally appeared on Medium.
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When he is not working on Scalr, Sebastian likes to make sushi and play rugby. He also writes in the third person but feels slightly weird about it.