When a Femme meets a Butch... dating advice!

[Dance-with-me]

OK, I realized today the implications of having done only the "online dating" thing for the past 15-20 years: I haven't dated someone that I met first in person since... 1993?!? No, actually 1998 (very briefly) but still, WAY too long (and I was much younger - obviously). When you meet via an online dating site or forum such as this one, you at least know before contacting each other that you're both single and potentially interested in meeting folks to date. When you meet in person, there are just so many more unknowns!

So today I met a butch (or at least I presume a butch identity, though I have been wrong in the past... so how do I even know that?) who is close to my age, interesting, attractive, responsible, smart, funny.... and it made me realize that I have not the slightest clue as to how to indicate a possible interest or even find out if she's single. We met to discuss my possibly volunteering in the community to help with something she runs, and we met at my job with her coming in uniform from her job, so it wasn't a social call at all.

I'm not even certain that I'd be interested in possibly connecting with her socially, but I still want to figure out more about how to do this - in this day and age, how do you handle it when you meet someone where there might be a connection and yet you don't even know if they're single? If you find out that s/he is single, how do you proceed from there - especially as a femme, and especially as a femme who can be quite bold when her confidence is up but can be super-shy if I'm not sure how my interest might be received/perceived.

We discussed briefly some things that we've seen posted on facebook, including some organizations that we both follow through facebook, and from that I found her on facebook - would it be completely inappropriate to send a friend request? Or is that something that I should leave until I've meet her several more times (which won't be happening any time soon...).

(Good grief, I'm 53 years old and feel like I'm dating for the first time again... UGH!! Clicking Submit before I chicken on on even asking about this!!)