Most relationships attempts are near misses. I really don't ask women out anymore, but since joining this site I started recalling a number of women interested in me that I just let slip by over the years as I slipped increasingly into isolation.
Some just weren't my type (too slutty, pushy in trying to get me, just looking for a one night stand, way too friendly with other guys infront of me), but usually it was because we lacked a romantic component or friendship that I let it go. It's something that needs to be established first before I jump into a dating scenerio where I'm comfortable.
I'd be perfectly okay with the idea of a woman asking me out. Just I'm uncomfortable with a strange woman asking me out, asking all sorts of HR like questions over a expensive dinner and then who knows what. If a woman knows me then she would already know what I would like to do and even better, what I wouldn't want to do. A example of a really bad date night for me:
Cook me shrimp alfredo with white sauce (this actually happened to me, I kept sweating and had to get up to puke a few times while smiling a big fake smile in between while eating it).
Then we go to see a play (good), Hamilton (bad, might as well be the Vagina Monologue).
Take me out to a bar to get me drunk (I don't drink, I'm a member kf the prohibition party).
So many ways for that to go wrong. And I agree women have to put up with that, but they seem to accept it in exchange for getting free meals and entertainment and romance. Heck, women just sit in bars and let obnoxious men they won't ever sleep with buy them drinks, so clearly the female brain works differently here. But if it was a woman who knew me, I'd be more trusting and would probably be okay with a surprise date set up. Blindfold me and bring me places.