I want to ask you guys if i should approach woman in my hometown, developing a habbit of approaching woman everywhere or should i go to bigger cities on weekend and practice then? Is 44 thousand people enough to not have fear of judgment hanging over my head?
And also how do i get better at closing? Will i get better as i will start to date more woman or are there any other tips that you can give me?
Yes 44.000 is big enough. I've approached at a university with a population of less than half that number, never got a bad reputation out of it (if anything I was the social guy). Just don't approach creepily.
As for closing, check out DiCarlo's escalation ladder.