I asked a woman out a few days ago. Conservatively-dressed Muslim woman (wore the hijab), actually.
We were at a professional event together, several days, and she seemed like she was really into me. It started just that we were talking (part of a bigger group) at a table for much of the day, but something got her on my mind, I think her asking what I had planned for after all this was done (I make it clear that I've got nowhere to be) and I was hoping she might sit by me later. She actually did, made a beeline for the open seat I left beside me, and then kind of clung to my side to ride with me on a bus.
So on this ride I make a point to get off the subject of the event and onto hobbies, which she lit up/got excited when I asked her what she does for fun. I felt like I was being real smooth with it. She mentions going out to the country to pick fruit, I mention picking berries with my mother as a child and still picking some off the bushes when I take a hike. She has X brothers and Y sisters, I have Y brothers and X sisters. Gets into family stuff, starts to get more personal, opens up a bit. At this point it feels like it's turned, in some informal way, into a (short, 45 minute-ish) date. If I went wrong anywhere it was getting into faith a bit with her. But when we got off the bus I didn't know how to tie that off and cowardice took over and so when she got into a conversation with another person I slunk off. I pondered over what it was I expected or wanted. In the biggest flights of imagination it would be to take her into town and sleep with her in her own apartment. In reality, I figured it could be nothing but a one-off date for its own sake, and I actually liked that idea.
The next day, last day of the event, she sees me at breakfast. Beams with the biggest smile and waves at me from across the room, which makes me feel like a million dollars. I make a point to, early on, ask her what she's got planned after all this, but her answer isn't encouraging. Busy work, deadlines to meet, go back into town (she lives there locally). There's basically no time to do anything after the event is over because the dinguses that ran it scheduled it way too full. Then we just wind up at different tables, you go to these things, you don't want to hump one person's leg all the time, you know. You'll make a few friends and focus on them, but you don't monopolize their time. She does seek out my side after that, tries (though the need to pack people in closely separated us) to get next to me in the group photo.
Finally what I did was, waiting on another shuttle, I just wait for her to pass by, compose myself and ask her if I can sit with her. She's seeming a little perturbed now, like maybe she's realized what's starting to happen. Now, I have decided before that I don't care for contrived flirting, "game," any of that shit. Flirting comes in just in the playfulness of how you speak with them, body language, games with the eyes (stealing glances, if they're open to you they'll probably find an excuse to approach you). Physical escalation I am still absolutely awful at. It will work on my own terms or not at all, so I approach in a manner that comes more natural to me, which is warm and old-fashioned (down to choices of word like "smitten").
I tell her upfront, but happy/sweet expression and all, that I've become smitten with her and would have liked to take her out, but it's not clear how that's going to work logistically. She asks for clarification, do I mean a date, yes, then she starts to explain, mildly upset, what a courtship is and that a Muslim woman cannot marry a dhimmi man and so on. I let her know that I understand, told her how sweet she was. She asks for my number, actually asks me to exchange contact information. I wanted a photo with her - a friend I made on a past event wanted one with me, and that got me in the habit of taking them with the people I talk to more - and she was happy to take it and wanted a copy herself. And ask me if I was going out to dinner (hoping to see me there, though it was actually the last we talked; I didn't want to pester her and we just didn't happen to wind up at the same tables, that's how it goes).
Despite my disappointment, which would rise and fall like a cycle, I went on to have a great dinner talking with some of my other favorite people and had other nice conversations before leaving and a sense, in conjunction with my religious practices on the way home, that everything was in harmony in that moment.
Looking back on it all, I really do think she was attracted to me, but perhaps subconsciously, or without any ambition. Attracted, not attracted enough to violate her religious precepts. Either way, I feel like she took a real shine to me, romantic or platonic.
My largest issue has been approaching very little, and also feeling like women look right through me, which was not the case here. I made a point to make myself be decisive. Most well-adjusted men learn to overcome fear of approach/rejection in grade school and then to build confidence through what successes they do have, because even well-adjusted men will miss more often than they hit. But there is a complex of maladaptive thoughts that the kind of men who post here, self included, adopt. One such is an anxiety that rises with the stakes. The better it is going the more seriously you take it, then perfectionism sets in (you don't want to blow it now) and decisive action never happens. The rarer the attention is, the worse that is because the individual feels like a person who is suddenly starving. I made a point to avoid that, except perhaps for if I could have tried to touch her on that bus, and I don't know that it would have been welcome. (That is one point against her having been attracted, but also filtered through culture. She came across as very comfortable in my presence but not physical. I don't recall having made her laugh much either, didn't really joke a lot.)
There is also an importance in how a person processes their disappointment. In the long run the only women you really remember are the ones that were a major part of your life, either because you had something with them or you tortured yourself chasing after them for too long. Which for me would be three women across some ten years of adult life, one girlfriend, one that went on dates but just strung me along, one that I went three years before asking on a date. But I think it's fair to say I hadn't asked any woman out in years until one last year, and then one this Summer, and now this one just two months later. That fear of approach/rejection can only be overcome through desensitization, and I actually do feel, in some ways, a surge of confidence after being rejected (because the world didn't end). But the last one who turned me down, well, I didn't actually ask her on a date. I was trying to get more time to talk with her to build up to the date. But it didn't go anywhere. Reason I bring it up is that I felt bitter/uncharitably towards her, and for little justifiable reason, it was just sour grapes. This woman left me feeling some mixture of acceptance and loving (it's not going to happen and I like her even more because of how kind she was) and impressed by her.
