I already asked this question on r/dating_advice and I want to hear what guys on here have to say.

I will share the original paragraph I shared there earlier:

So I’m a guy in my mid 20s and I’d like to think I’m very social, but I’m always puzzled by this cold approach interaction. I’ve walked up to random girls during my undergrad years and told them I thought they were pretty and tried to get their number, but I always got the vibe that some were weirded out by it despite getting numbers. A lot of times I walk home after work and I see so many cute girls and the one thing running through my mind is ‘is it gonna be weird as fuck if I tell her she’s cute and I just wanted to introduce myself?’ Or is meeting someone suppose to be a ‘natural’ process you gotta wait for. I don’t know.