I think the major problem people have with being afraid to pursue relationships is that they don't realize the very basic truth - women are just people, you really don't need to treat a woman like some kind of foreign creature.
The vast majority of women will say yes to a coffee if you even have the most basic purpose to ask. "Oh yeah? You work in realty? Listen, I've actually been considering getting into property flipping WAAAAY down the road... blah blah blah" wait to see if she has any advice on that, and then try to chat more, and then "Listen, I'm a little busy, but perhaps we can grab a coffee some time?" Or, "Oh! You work with So-and-so, well... I actually have some questions about that guy and his business, if it's not too much, perhaps we can grab a coffee to discuss the blah blah thing So-and-so is working on." And just remember, women are only people.
And these women you are asking out for coffees aren't even necessarily ones you'll wanna date, this is networking. But women generally know other women, and women LOVE to introduce people to one another. Just keep networking, and flirting around, and eventually ask someone out for some drinks.
Now, if you're looking for romance - a trick I always used to use is party hopping, basically I was always going someplace else more exciting (usually the party-bar-party formula works, because people at bars are looking for a party and people at parties are looking to go out to the bars), and I'd try to gauge which women were interested in coming along. You really just need to drum up hype for it.... but don't be a douche and try to kill someone's party if they want people there.
I don't even think you need any spectacular social skills or anything to meet women, you really just have to be a human being with some kind of topic. It's basically not any different than drumming up interest for a forum post, just talking instead of writing.
Also, keep in mind, if you look for women you WILL eventually find them. There are disgusting numbers of single women looking for relationships out there, and contrary to popular belief in the MRA communities, about 90% of women are quite good company... And the really interesting thing is that women who are generally more attractive/more intelligent women seem to be also be much more open to simple-casual dating.
Flirt a little, then some more, and if she says she's not seeing anyone, or indicates it, that's usually the "check" moment, don't be afraid to go in for a kiss at the end of a date, the most clear sign she wants one is a smile, that's the checkmate moment. And sealing the kiss, and you have options then: don't get desperate and try to push your luck that night unless she brings it up first, because you'll pretty much certainly be getting some action on the next date; and as you're anticipating it, so is she.
I mean, that's not to say you can't get action on the first date; but usually that deal is sealed pretty early on in the date, not late in it. There's a difference between flirting and outright hitting on someone. If you take her out to a club, and dance with her, sparks might fly there, and then you know things can go further (it's never a mystery).
Anyway, I'm just ranting and rambling. I've been out of the dating game for a long time now, but I can't imagine much has changed in the past decade and a bit. I still ask women out for coffee with no romantic intent (although, sometimes women can get confused on that, even when they see the ring on my finger); but for the "blah blah blah" reasons above, just far more honest about the reason we're going out for coffee =P
Actually, I will say this, try to make the reason you're going out honest, because if they know it's bullshit, then you sort of break the flirting spell. People in general like honesty, and they like people being themselves, so make sure you do that. And there is a world of difference between being yourself and doing things that you yourself don't necessarily do, like "asking people out to coffee is not in my personality" isn't really a thing.
AHHHH! I'm going on and on again. Need to get back to work.
I describe myself as a little dose of toxic masculinity.
