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helldalgo comments on A Rationalist Guide to OkCupid - Less Wrong Discussion
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Facebook friends are a non-think button press or in other words, pretty much nothing (unless you keep in contact, and in that case they're just friends)
My idea for the next incidentgate is (and seems kinda silly when typing it) "Hi I remember you from HS and always thought you were kinda cute but I was too shy to talk, would you like to meet up sometime?"
PEDANT EDIT: There's also a few girls from middle school before I moved, (Same city, different school)
Also, I might want to have a short introductory conversation before that message. Don't feel like this should be copied word for word, but something like this:
You: "Hey, how's it going?"
Her: "Hello! It's going well!"
You: "I saw [recent mention or post about something relevant to both your interests, non-sexual]. [Comment on thing, keep it positive]."
Her: "[response]."
THEN maybe the high school message. Again: autism. So don't take my advice as the pinnacle of social skills. :)
It looks like a conversation with a person I haven't talked to in something that isn't either long enough for them to forget about me or someone close I haven't talked to in some time.
But let's be pedantic and you'll probably like this or the autism stereotypes aren't true, here's a few scenarios:
Your example will probably work on category 1. Category 2 MIGHT go along, although a simple hi is rather generic and therefore is more of a lottery bet than a sure bet. I can't tell how category 3 will respond, but probably not better than category 2.
Consider how you'd feel about the introductory messages if you were from each of those scenarios.
We could also dive into sub-scenarios, tailored to specific optimisations or lack of them. Such as my fashion choices, how I live, people I hang out with, etc. Although it's dubious how much they matter since all of this is my unresearched model in my head about online messaging.
You are correct, (some of) the autism stereotypes are true in my case!