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?

Hi Dan (Dan Druff ~ Interesting name there )

As you feel so comfortable together you could say something like:

'I feel that I want to talk to you, about something which might 'weird others out', but which shouldn't be awkward for us, because we talk about everything. However, I am terrified that this might bother you, and that you might find it awkward, after all. Can you just hear me out and give me an objective response, please?'

Just put it into your own words.

If she is co close to you, and has no other boyfriend, then it is possible that she feels the same way you do.

Good luck

You know what, I am going to take this advice. I mean, from outside looking in, it is easy for others to say what they would do in this situation. Most never will take any advice from others, but they sure do like to hear it. I think that the best thing to do is to just ask her about all of this. Some people tell me that back in the eight grade that she liked me, while others say she didn't. I am going with MY viewpoint on this, not others, and will do what has been needed to be done from day one. If it doesn't work and she looks at me with the strangest face I've ever seen, then I will laugh probably, and discontinue these feelings as best as I can. After all, we are both really really REALLY weird, awkward people and that is why we get along is because we do not mind it. If this works and she really does like me, then I know who I am going to marry already; I am that confident. Tank you.

Hi Dan

Honesty and clear communication are usually the best way forward.
I do realise, though, that it isn't necessarily easy to do the best thing
I hope that you will get the response that you seek & that you will both be happy with it.

Good luck!

my opinion is to tell her how you feel and say that you want to try to be more than just friends. i hope everything works out sounds like the two of you are good together so why not give it a try