Advice for a guy in his 20 s who’s terrible at asking out daughters in random places

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I’ve been single for over 2 years, and haven’t been in a relationship since college. Since graduate, I’ve rarely been in situations where I can meet daughters my age, as I’ve been the youngest one by several years at most of my jobs, and has been a similar experience. So I’ve been trying online dating, and had terrible results. I rarely get matches or responses, and merely been on a handful of dates, usually never hearing back from them after the first. Which puzzles me, as I did alright in college. The whole affair has only injury my self-confidence, and caused me to dwell on my flaws, to the point it’s hard to imagine I’m the same guy I was a few years ago.

So I’ve realized despite how much I’ve wanted to avoid it, I need to try picking up( not in a pick up artist sense, I’m not the sexuality preoccupied kind of guy) girl I see in random places. I largely conquered my social anxiety when I first started going to college, but one thing I’ve never get used to is starting conversations with daughters I didn’t have a reason to talk to. It was easy at a club or classroom, because we have something in common and a reason to be there. Striking up a dialogue at a supermarket or bookstore is different. Even if I go somewhere like a convention, I’m reluctant to talk to a girl even though it’s in a strictly platonic and friendly route. I’m not sure how much of it is my newfound lack of trust, but I’m a little too self-conscious to start up conversations with them, because I worry about coming off like a perverted crawling, or if they already have a boyfriend.

I guess this is a longwinded route to request advice, either from guys with more dating experience or get where I’m coming from, or women who understand how the girls I want to ask out believe. I’m sure I come off as pathetic, but I would appreciate any help.

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