The excess of choice made me wary of missing out on my perfect match. To make sure I wouldn’t miss out, I designed a rigorous first-date process. I went on 150 first dates but didn’t manage to find the One. At some point, we got lost and I used this opportunity to steal a magical first kiss. I wanted to tell her that I liked her, but I was anxious that she wouldn’t.Most of the first dates led to nothing: we didn’t have much in common. 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. That was my best first date on more than 150, ironically the only one that hadn’t been part of my rigid routine. On our 5th date, she said she wasn’t ready for a relationship. Having more matches increased my odds of finding someone interesting, but it also became an addiction.I needed to come up with a rigorous and scientific process. You need a certain amount of candidates to be able to benchmark what quality means, and humans are really difficult to assess. 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. Openers, follow-up messages, swiping, bookmarking, text messages and phone number recording. 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. I became an online dating magician who knew how to optimize a profile — A/B testing pictures and message.In computer science, this is known as the optimal stopping algorithm, aka the secretary problem. An abstraction layer capable of managing online dating for me: My first problem was solved: getting leads into the pipeline. 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.
But my goal wasn’t to fuck around, I was here to find that special someone. We took turns, and she rowed with the vigor of a thousand vikings. I’m a fat, bald, short guy whose only quality is that he isn’t an ax murderer. Since I’m 31, and eventually want a family, I figured I’d better not procrastinate. For any serious endeavor, you need a serious process. I decided to hack the system and go for volume instead of personalization. I was determined to find the One, even if it meant swiping right the whole Bay Area.Another was exceptionally caring, and made me feel special, valued. 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.