Well here is the deal I’ve know this girl for a couple years, we’ve become pretty close friends but nothing more. She started hanging out with me and my group of friends and just became on of the guys, so to say. It comes very natural for me to be able to talk with women, but with her it is very different I cannot even innocently flirt with her. She in every aspect is innocent. While me on the other hand I’ve “been around the block”.
My question is what would be the best approach for my situation? And, without the line I dred to hear her say “I wouldn’t want to risk our friendship”
The old “club 'em over the head and drag 'em off by the hair” routine always worked for me.
I think your query would recieve a better response over here…or you could just wait for Manhattan or your cousin Nickrz to do it for you.
Nicklz said
She in every aspect is innocent. While me on the other hand I’ve "been around the
block
You sound like she is 12 and you are 30. What is your age difference.
To Quote Sheena Easton
If you love somebody you let them know. There ain’t a lot of time before it will snow."
It may sound trite, but sometimes it’s better to make the wrong decision than none at all. If you’re going to be pining for her everytime you meet, or miserable anytime she’s with somebody else, then you have to ask whether you can accept that unhappiness for the rest of your relationship. If you can, fine. If you can’t, tell her. It might all go pear-shaped, but at least you’ll have tried.
I’ve been there - said my piece - got knocked back. I watched as she went out with some really dodgy characters, but bit my tongue. In the end I was lucky; we remained friends despite my admission, and I moved on eventually. I don’t regret it; at least I didn’t have it eating away at me on the inside.
Good luck.
Once, a long time ago, I saw an old book called something like “101 ways to say I love you.” You know, say it with flowers, put it in a note under their windshield-wiper, etc. My favorite was “Carve it in balsa wood and leave it floating in the toilet.” I told myself that someday I’d find someone who could see this as a token of true love. 
Your Quadell