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HughRistik comments on The First Step is to Admit That You Have a Problem - Less Wrong
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Imagine a society that put non-trivial effort into helping the type of male HughRistik described in his comment here and in the previous discussion, and that actually updated its advice as it learned what worked and what didn't. One where you can openly give effective advice about what a man should do to create interest from females without being ridiculed.
Compare it to the present society. Do you see a difference? If so, you are in agreement.
Despite the humor in the comic, that is a real danger: men do have "something to lose", well above and beyond the feeling of rejection: he suddenly becomes a "pervert", the woman tells others about what a loser he is, etc. I know because I have lived it.
What's the difference between a romantic act and a pervy one? Whether the woman has decided she likes the guy doing it.
One thing I'll add is that I don't want people to think from either of our posts that dating is only a problem for shy or interpersonally-challenged straight males.
I was once at a club talking to guy I met who turned out to be gay. He was telling me that he has no idea how to approach new guys at clubs. He said something, "well I could go up and ask if they want a drink, but that feels cheesy... and then what?" Clearly, he is aware of the socially acceptable taskification (buy potential partners drinks), but finds it inadequate and feels lost about what concrete actions to take.
Everyone except naturally adept and popular kids suffer from the norm against taskifying the dating process, or using taskifying to learn how to develop dating skills and attractiveness. Males are just the only population that date from a pool of people who typically (a) are more selective than them, and (b) expect them to be the primary initiator of advances.