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For reference, I'm in my early 30s. A random guy trying to ask me out would probably be a no-go, just for the fact that I don't even know you. Probably because I'm kind of sheltered and don't tend to strike up conversations with strangers. Maybe if we were at coffee/book/record shop or something and had a nice conversation first (so that I could at least gauge if he's a weirdo or not), and THEN he asks me out.
Actually all of the people I've dated were people in my friend circle, friends of friends, people I went to school with, or coworkers. This kind of proximity dating has been enough for me since I've never felt.. romantically lonely (I'm not gonna count highschool lol). I've never done online-dating because I've never felt the need to.
Basically I'm saying the random approach would probably, most likely, not work for someone like me.😅
I also think we've all heard plenty of dates-gone-wrong type of stories – and you hear a lot because the world's very connected now and we love to share. And so that certainly makes a person more guarded, wary.
I wonder what the older generation's dating experience was like. I'd like to think they were more outgoing and trusting and had an easier time! xD