GabrielDuquette comments on [gooey request-for-help] I don't know what to do. - Less Wrong Discussion
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I'm not quite as active on OKC anymore, but when I was, I'd write to lots and lots (hundreds, over a year) of people (girls) with near-zero expectation of response. My guiding star wasn't friend or romantic partner, but "do I want to know this person?" I've written to at least one dude (in my area) who I thought I'd click with, but he didn't write back. I get along with girls better anyway. My checklist:
Check pics. Am I attracted to this person? I'll still write if the profile is extraordinary and/or I sense that our friendship will be a solid one. Stipulating friendship right out of the gate isn't a problem for me.
Have they answered more than 400 match questions? The match scores should be robust. Are we over 90% match? Over 80% friends? Less than 10% enemy?
Is their "dating persona" something non-alarm-bells-y like The Maid of Honor? Although, I admit a curiosity about girls who get Genghis Khunt or The Battleaxe, if their profiles are otherwise inviting or innocuous.
Check "unacceptable answers" in the match questions sidebar. Are they religious/agnostic? I don't want to get into arguments about solved problems. Are they very politically correct? I don't want to tiptoe. Are there unusual inconsistencies? I don't want to deal with a compartmentalizer.
Now I look at what they've actually written about themselves. Are they articulate? Do they possess knowledge I do not? Are they funny? I don't care too much about preferences like music, books, etc unless there is something tellingly atrocious in there like Korn or James Patterson.
If all of this comes up clean, then I initiate contact with a short, clever message pertaining to some specific part of their profile. If they respond, after a short exchange I try to steer things toward a chat session -- the real test. If our banter is self-generating, then this person is added to my gchat list and away we go! Sometimes people start out as potential romantic partners, but end up as friends because of untenable distances or plain old lack of romantic spark. In summary, I think it's possible to gain a lot from your OKC experience if you don't have binary notions of friendship and love, don't disappoint easily, and are willing to put in the time and effort to succeed.
Thanks so much for the detailed response.