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The social context of being at church, for example, demands radically different behavior than being at a nightclub.
the accepted social context, then you end up making people uncomfortable.
Pushing and pushing for Spelman to respond to him, switching social media platforms when she wouldn’t respond to him on the previous one?
This is someone who’s demonstrating poor social calibration; he’s getting a very obvious brush-off and keeps trying anyway.
A 5th level paladin isn’t going to survive going through the Tomb of Horrors and somebody who doesn’t have much social experience is better off sticking to accepted social spaces to approach women.