Hello. I would like to share a story and to have someone possible help me out with this because nowhere have I found a story similar to mine.
So, I have known this girl for 5 years, more or less. Long time, eh? Most of these stories I read were that they had known the woman a year or so. Well anyways, when I first met her, I had a huge crush on her, but I was only in 8th grade. I had no idea of the dating world so I sat silently every time my other best friend wanted to talk about the situation. Because of this, I stepped out of the "date" zone and into the "friend" zone. I did this because in 8th grade, I had no idea how to flirt or even if this girl liked me or not. One other person said that she liked me but I was stubborn and let the situation ride.

Since then, me and this woman have been great friends. She even likes me more than her woman friends, so I hold a high status with this girl, and I feel the same; screwing this up could be drastic. Well we are the type that don't flirt. I take this no differently because she doesn't even date guys. Her last boyfriend was before I knew her. She isn't good with flirting either because of this, and she hasn't even kissed a guy yet. So in all honesty, I do not know how she would interpret my disposition towards her.

My goal is to ease into the conversation and talk about this whole mess. I know it wouldn't be that awkward because we talk about everything, so talking about this wouldn't weird her out. But then again, it might and I am terrified. What steps should I take here?