Go for it! I'm sure she'll say yes, just be your gentlemanly-self. Ladies always love a gentleman.
Do you already have a plan for what you'd like to do? If so, tell her what your plans are. Then tell her you'd like her to join you. It will alleviate a lot of the stress.
Well, the plan was ask her out to the range and then to dinner (she's a gun nut like me). I could couch it that way.
Perfect. "I was planning on heading out the range on Saturday for some target practice, then maybe get some italian food at this place I really like - I would love it if you would join me."
Look at you, you sexy bastard! Her answer will be "HELL YES!"
Oh, my value as a man is certainly independent of that. My value is based on many things, but whether this woman finds me interesting has nothing to do with that. My value rises daily in fact, it feels like these days I'm walking taller, running farther, and generally happier.
I am back at up-front conversations like this. I hate calling people on the phone for the first time. I hate walking up to strangers. I hate asking women out. It's just a mild social phobia (which I wager is fairly common) that I have to push myself through.
I'm 99% positive she is single. We've been acquaintences for about 2.5 years, and a year and a half ago I expressed interest while she was breaking up with her boyfriend. I did some dumb shit and ended up with someone else.
In the intervening year, I've changed and my co-volunteers have also noticed that there is a good possibility that she is interested in me. For example she's been volunteering to help me with nearly everything that I run, wanting to go on visits and even offering for me to keep my bicycle at her place instead of at my ex's where it still lives.
I figure, I ask her out to go do something fun outside of the organization instead of always hanging out while we're volunteering is the right way to go.
The rejection itself doesn't bother me. It's actually preferable to the anxiety that proceeds the question.