<human>: I'm something of a failure when it comes to dating and romance. In high school, I had a boyfriend (who started out as a good friend), but we dated behind my parents' backs and after 5 years, it got ugly and we broke up. In college, I went to a women's school, so I didn't have a lot of opportunities to casually meet guys. I'm pretty shy, and at the time was extremely depressed, so I didn't go to a lot of parties or try online dating. 

Most of the advice I've gotten over the years is to "wait for a guy to make the first move" and "love will find you when you aren't looking", instead of actual tips on meeting partners. I'm fairly average looking, but with pretty horrendous self-confidence issues, and I think people can tell that, which is why I've never been asked out or flirted with.

Cue now, where my life is moving in a positive direction and I really would like to start dating. Trouble is, I have no idea how. 

For instance - there's one guy I encounter regularly (he's a frequent customer at the store I work at) who I chat with, and would be happy meeting up over coffee - but it feels weird and uncomfortable to just send him an invite or message, plus I don't even know if he's single. Living in a small, rural-ish town makes things harder - there aren't bars or meet-ups to go to, and going out to the nearby city is a weekend-trip affair. Most of my friends here are already in long term committed relationships too, some with kids, so there isn't a lot of 'going out'.

Honestly, I'm looking for some concrete advice on what I can do or scripts to use to start up conversations. It seems like really basic stuff that I just missed the boat on, but I'm tired of it and want to do something to improve the situation.

Condense the text into a few key points
<bot>: Never really learned how to date or ask/be asked out, trying to give it a go in mid-20s