I grew up in the "garden district" of my hometown, dominated by people on the social register all of whom sent their kids to a handful of same-sex private day schools. Note my family was not themselves on the social register. Anyway, if you were at all popular in that neighborhood you literally knew every other kid your age. Popular girls who'd never met me knew who I was by reputation. Girls who weren't popular were socially isolated due to attending same-sex schools. Needless to say, I didn't have much of a chance.
However I was apparently somewhat attractive despite being a pariah, and when I would go to a summer camp or similar situation, girls who knew nothing about me were friendly in a way I never experienced at home. My first experiences kissing and making out happened in those situations, unfortunately over time I would start to make enemies and would be as unpopular at camp as I was at home. There was one case of a girl who continued to like me, although she lived in another part of the country but I did visit her, however she had some serious psychological issues and there was no future in that either.
Yeah meeting girls away from their usual "crowd" can work in the short term but doesn't change the fundamental issues.