Nervous about asking a woman out

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There is a woman that I see at church a lot that I am trying to work up the nerve to ask her out. I think I have a shot, and I probably will do it soon. Often, I can work up the nerve.
The only problem is I am bothered by the fact that, over the years, a lot of women have become really annoyed and disgusted when I ask them out. I can't figure this out. I have looked at how I present myself, and how they are acting, and I have tried to analyze it systematically, AS style. Its a combination of (A) I pick the wrong kind of women to ask out, (B) I am Ok as far as looks go, except I am somewhat overweight, and overweight in a strange kind of way- all my weight goes to my belly, so Iook like a skinny guy who's stuffed a pillow under his shirt. (C) Because I have had problems, I am always stuck in an environment where I am smarter and harder-working than the people around me. I went to a mediocre state college as a commuter, and have a routine government job. Sure I get promoted a lot, but its still routine. Plus I live in a poor white neighborhhod. So here I am, a dweeby yet creative aspie chasing women with bleached blond hair and thick Boston accents who lust after bartenders and cops and bikies.

Right. Well, at least you are taking the shots. That's more than many aspies will do. So good for you. Ive made many bungled passes over the years. For some reason it doesnt bother me. I just laugh at them when I look back. The ones I regret are where I didnt try.

I have no idea what works for you but I'd wait for a good conversation day and then segue into casually asking her out as if it was an afterthought. Keeps it as low pressure as possible. As if it wasnt the only thought on your mind at that moment. And then beat a friendly but reasonably hasty retreat if it doesnt work. As for how people reject the offer? I think it's a character issue. If they can't do that well I tend to doubt that they were worthwhile anyway. There are many friendly ways to do it so there is no excuse for rudeness. But Ive bungled that myself so..

Thanks for the constructive criticism. Its pretty on target.

For a start, forget the word "date". She goes to your church so it is not like she is a stranger. She knows who you are.

Look for an excuse to get into a conversation that she is part of.
Then say "That was an interesting point you made. Would you like to grab a cup of coffee at the local cafe, because I would like to discuss it further?"

If she says yes then you are in the running. If she says "No, I have to be getting home. Perhaps another time." then at least you haven't made a fool of yourself.