First off I'd like to say that I have been referring to this site more and more over the last few days and have noticed significant improvements when it comes to my interactions with women.

I do need some help though with this HB8 that I work with.

She somehow found out that I liked her, so then I had a mutual friend of ours talk to her and she has kind of been guaging where I am at . The interesting part though is that she knows that my friend is trying to help me out. The first time my friend brought me up, this HB8 said that "I was cute but that I was too sensitive" So, throughout the rest of the day I had her and everyone else at work cracking up because I was "jokingly" trying to be a badass, to qualify myself to her. I then flipped it on her (HB8) saying that I did think that she was cute but I only did this was just a way to make the day go by faster,but that it was hilarious, and we should just go with it. I did this because I realized that If i legitimately try to be a certain way for her that I would lose her . This also takes the pressure off of the situation So at that point, I am just a funny guy who isn't taking this too seriously. This isn't the textbook approach by any means but it has kind of been working.I was very careful in my word choice so that I made it clear that I was not just a friend. So, then a few days later she said to me that she really wanted to see this new movie coming out. So i negged her by picking out this reallly strange guy that we work with "I could hook you up with him! If you are too shy then I could probably ask him out for you blahblah" instead of just asking her out directly. Then, after making fun of her for a while I said "Do you really want to go to that movie? I'm busy Saturday but I could probably make room for you on sunday" then she says "I wish I could but i cant im working all day sunday." (at her second job) , which was totally a legit excuse. At this point I was like "F****K"

So now I'm not sure what to do to keep things moving in a positive direction. My big joke about liking her and trying to be "her type" is over . But I need a way to transition into actually hanging out with her outside of work.

Should I ask her again ?

or should I try for something with a little less up front pressure like going out to lunch from work together? which is actually more risky because then I might become her "lunch buddy". buddy = bad.

I have been keeping at a distance because I don't really want to get in over my head and make a mistake. Obviously I need to do something because if I do nothing now then I will just dissappear from her field of view, so to speak.

If you guys can think of a good way to ask this chick out again without compromising her perception of me then I would be very grateful. I'm friends with her on FB and I have her #. I know I need to ask her but It makes it a lot more difficult when she doesnt say something like " wow this (insert activity) sounds awesome" How do you ask someone out without losing that power that you had while being CF. Doesnt asking someone out contradict what the whole play hard to get thing is all about?

just my advice:

I think at this point you need to give it a few days just so you dont seem too desperate and then ask her again, but make sure she takes it seriously, dont joke around with it. I think this will show confidence. If she still says no I think you gotta be done with her unless she gives lots of signals in the future.

Lemme know what happens