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One decided to end things despite “having enjoyed her time with me, for what it’s worth”. In the process, I also found out something horrible: I still believe technology can hack love, though that belief is likely irrational.

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.

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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 I jump too fast to intellectual conversations, making it awkward. I wanted to find the perfect match, so I wasn’t going to be an amateur about it.

I’m told it’s fear of appearing desperate, but fuck that! The whole point of automating was precisely to make it not so. PS: I will not open-source the code since it could be used to hurt people, but I might share it if you ask nicely.

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.

Dating at scale doesn’t go well with well fitting areas of interests. On the rare occasions when I was genuinely interested in a date, she wouldn’t be. With her there was no doubt: I needed a second date. Outside, she climbed on my shoulders and I ran uphill while she laughed. 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.

Another issue is that culturally relationships are driven by men, at least in the first innings. Who knows, perhaps I’ll find my special someone through this post?

This is different in the more progressive Scandinavian cultures. I want to thank the amazing women who participated involuntarily in this experiment.

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