LOL you sound somewhat jaded doc, I agree he needs to know how to talk to a woman but if you relax and have fun that will naturally come as part of the situation.
if that person is going to judge you like that is that really a person you want to associate with? probably not, so why even wonder what they think?
just be yourself and have a good damn time with it the rest will follow.
People are going to jump at conclusions, no point helping them, LOL!
It's essentially impossible to not be judged on some level. I'm simply arguing people should be putting significant negatives out there in a less harmful light.
For example: "Taking time to work on my career" can at least start a conversation about work, education, dreams, goals, and other good crap women are looking for. "Hanging out and having a good time" makes them wonder if you've got Peter Pan syndrome, LOL! "Looking for Miss Right" is probably worse than saying "I just want to have sex".
Had you written "Be good company to yourself and the rest will follow", I would have agreed. People who consistently stay in a good place, on the inside, never have too much trouble finding anyone to hang with.
I still don't see how/why people think a dog or puppy will be a good enough conversation starter for the shy. Just walk up to the chick and introduce yourself. if you get shot down keep repeating the process.