I can't say I know exactly what you're going through, but I can feel your pain to a large degree, Aeiouy.
I remember the first girl I went after when I stopped going to meetings. I'd been reading a relationship advice book called The Game and talking about its content with a couple friends, so I felt ready to try my first stab at seriously trying to meet non-JW girls. Mind you, I was about as socially backward in that area as one can get. I'd had no secret girlfriends because the org said not to. All my efforts to meet a JW girl didn't work. I had no experience in what to do, but I felt the need to press forward.
I met "Brandy" at a karaoke bar with some friends. She was fit and attractive; the first night meeting her went very well, I thought. We met again with the same group of friends the next week, and it seemed she really had a thing for me. I interpreted her signs as indicators of interest in me. Later that night, we hung out at a friend's house, and a really turned on the flirting. I made my move. Oops! Too fast, too soon; I got shot down somewhat. Later she apologized for flirting and I accepted her apology. Oops! Wrong move, again. We all ended up sleeping over at the friend's place, and in the morning, she seemed somewhat distant towards me. Two weeks later we went out again, and I was informed that she wasn't interested in sleeping with me, even though I'd never brought up the subject. But I eventually figured out what went wrong. Her indicators of interest were just drunk flirting; she did that with lots of guys. And, as it turns out, Brandy was good practice to make some rookie mistakes on, because right now she's in Kansas.
Things right now are better than they've ever been, even though the progress is slight. I have a friend with limited benefits--not a genuine girlfriend, but close enough. She was my first real kiss at age 24--so think about that! It just all worked out, even though I have no leverage to speak of in any category. But this friend with limited benefits has been tolerant enough to let me figure out things I should have figured out about 8 or 9 years ago when it comes to girls, so the situation is just fine by me.
Aeiouy, you've been given very good advice, to which I will add more: have financial leverage. I don't know what kind of work you do, but hopefully it's something that allows you to make a decent living. It gives you so much more of an advantage when you give off "provider" status signals, you wouldn't even believe...
But yes, being raised a JW makes you sooo awkward when it comes to "game," just try not to let it get to you too much. Work on making your money, and making yourself buff. I'm at least getting the second part right.
