Do women like shy men?

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...I am a shy man I suck at approaching most of my relationships have involved women asking me out and not the other way around so I am kind of new to this, I am not good at this and freeze and chicken out but there is this tall chick I have kinda a crush on and she flirts with me and want to ask her out but every time I try I freeze and chicken out.

Many women find shyness appealing.

Most still want the guy to ask them out, though.

Why is that? This sucks I am a freaking shy coward when it comes to approaching!

Upbringing. Society. Shyness on the part of chicks.

Shyness of a man could even look cute, adorable to some women. Not all.
But in your situation if she gives you every sign, and you don't react to them, you're hurting her. She wouldn't know you're being shy. The last thing you want is her to feel ignored/hurt by your little reaction. Would you give up your shyness for her at least before she realize how shy you are? That's up to you.

The very fact they bothered to approach you means there must be something about you they like.

If i were to get a clear "go ahead", i would break my shyness (or try to).
Problem is that "every sign" that a woman might/will give, is all but invisible... they need to be a lot more overt. eye-games/hair twirls and what have you don't work.
If they were to do something subtle like planting a kiss on my face, i might get the hint (might, or just assume she's drunk/lost a bet)

I lol'd.

Me, too!

That's a perfectly ordinary greeting actually. I encountered it first only last year (wow thanks, western standards) and whenever my social life picks up again, given that I know cool girls, I might make a habit of that.

I don't think that is even possible. It would only be possible if you selected to be shy, but that is not how it works.

I've had a sure go ahead several times, but it makes no difference.

I think shyness can be very appealing, but it can also be misconstrued as a lack of interest, or unfriendliness. I think that's why outgoing, more confident people tend to have more success.

...The ones who define success as lucrative bar hopping, less than five divorces and running another luxury car into the ground every few years because they were chasing not one or two but ALL the girls when they should've learned how to work with their hands.

It's definitely possible that she's not reading interest back from you, so is afraid to ask you out, same as you're afraid to ask her out. Would it be easier for you to ask her in writing? I've known some people who were asked out in writing and actually found it very cute. If you were to get a card and write the right thing in it, it might become a treasured possession of hers, and help you get it done. Could be an invitation card that has something like "Pizza Hut, 7pm" written on it; could be a cutesy leftover Valentine's card (like the ones elementary kids get) that you personalize to be asking out, could be just a random card, could be a homemade card...just something that's personalized and that has you showing through it. I've used cards a lot for things that I was too timid to say (just like hand it to them, let them read it and respond, instead of having to say it).

I have seen it expressed by some that they do...

I personally already have trouble initiating stuff, so I feel like trying to date a shy man would be hard...maybe out of my league. I mean I feel like the result would be the two of us awkwardly sitting in the same place not knowing what to say, or how to proceed with their shyness and my aspergers caused trouble initiating. I'd also be very self conscious about coming off to intently or strong and paranoid they'd be to shy to tell me if they feel like that or that I am going to quick with things.

The guy I am dating now is more outgoing in nature while I am a bit more introverted yet pretty relaxed/laid back as far as being open about things once someone does get me talking. To me that seems like a better balance I guess. I suppose I've always had an idea a couple should be like a team....like different strengths and weaknesses that compliment each other whilst having the same end goal. Rather than say two people with pretty much the same strengths and weaknesses who maybe have slightly different goals in mind.