@CugelTheClueless Sorry about the naughty word being the wrong one. I’ve never heard yours before.
I still think the lady’s friend is blocking you, because she and the friend have already decided that you aren’t the one they’re looking for. Most women are pretty good at being polite, while still trying to disuade a guy from continuing. You probably aren’t picking up on that. Sometimes the friend will come in to simply expadite matters.
I still think that looking for a good woman, for a real relationship in a bar, is about the worst place to find someone.
If all of your current interests are male dominated interests, then maybe you have to broaden your horizons. Try out some brand new things, that you may not have ever thought of, or may have thought of, but just didn’t pursue.
What kinds of things do you like, that you have described as male dominated? I’m thinking of something like comic-con or web-gaming. Is that what you mean? Comic con, is now actively persuing females with all sorts of things that appeal to both men and women. The online gaming thing isn’t helpful, only because it’s online. You need to find some new activities where you can go and be with groups of people, male and female. But if the things you are currently doing are mostly male oriented, then you need to find some other things to do (that you might never have considered before). Take some cooking classes (for a cuisine that you like) go to a singles mixer for some type of group that you sort of already belong to (religion, type of music, age group, divorcees, never marrieds looking to get married, potluck dinners). Join a book club (with males and females) if you have any type of physical activities that you like to do (that seem to have only males) then try something else like a bicycling group or a hiking group or a softball team or a group that regularly meets at the ice rink or roller blading group. Take some classes to learn some new skills that think you might be intersted in or join some clubs that you have never tried (painting, drawing, writing, acting workshop, tap dancing, line dancing, ballroom dancing, a garden club, a progressive dinner club, a wine and cheese tasting club, stand up comedy workshop, singing or karaoke) You have to broaden your horizons or you will just end up meeting the same kind of people that you’ve always met in bars. That’s always a crapshoot.
And if the places where you have been volunteering seem not have the mix of people you are looking for, then find some other places to volunteer. You have to mix it up a little bit and maybe find some new interests that aren’t totally male dominated. Ultimately, women won’t be interested in you in the long run, unless you have some common interests with them.
If your town has a local entertainment paper or if your newspaper has a listing for clubs and groups and classes and sporting events, start looking through there to find some things that you could try, that are likely to have both males and females in attendance.
And there’s nothing wrong with having a wingman to help you out, but the creepy guy you are considering is a horrible idea. Do you have any good male friends that you like and trust, that are not creepy? Women are afraid of and dislike creepy men, so if your wingman is like that, you will be deemed creepy by default, even if you aren’t.