Fear is what keeps people safe, but in turn, also what makes people miss out on what possibly could be the best thing to happen to them. It's never easy to assess situations like these. I was in your situation once, about 5 years ago. There was a girl who I've been friends with since the 6th grade. Once high school was over, I was one of the only few people she still kept in touch with. We hung out a lot, went to concerts together, get dinner together, and just enjoyed each other's company. It took me a while, but I told her how I felt about her. She responded to me about it two weeks later saying that she considered it, but felt that it would put me in a bad spot (I just transferred schools and she also had a kid). We've still kept in touch, me being her counsel when she needed someone, vice versa. And, while there are times when I still wonder if it can still be given a shot. But, of course, with the circumstances we're in (over 150+ miles apart, getting to see each other only once a month, her kid), I feel like it wouldn't work. 

You learn from pain. Both parties will make mistakes along the way but regardless of whether it works or not the important thing is the experience gained from trying because you carry that with you till death and it will help you grow so later on down the road you can deal with other peoples mistakes better and try your best to avoid the same ones you made otherwise you're just delaying the inevitable which you will have to face down the line. Just like a parent should let their child go put and get shirt to learn about life in a way no one can teach, you have to be good to yourself and push yourself to take a chance despite the fear of pain. It is rational and justified fear from past hurts but you cannot escape pain no matter how hard you try and I think the pain from failure, though more intense, is more short lived and teaches you a better lesson faster than the pain of disappointing yourself and feeling empty in life. That's my 2 cents on it anyway. Don't be afraid to look like a fool, everyone on this planet is a fool in the end. 

In my experience, it's hard to stay "just friends", even if you two are far away from each other. It's so natural to progress from feelings to a relationship, and you'll keep wanting that. But if she becomes some other guy's gf, you're probably going to end up feeling hurt anyways. The only way to keep yourself from getting hurt is if you keep yourself devoid of feelings. Once feelings start, there is always the potential of getting hurt. It's your choice how you want to get hurt: try a relationship and have things not work out, or having to get over her when you see her with someone else? If you give it a try, at least you know you tried, and it was just never meant to work out, and you can rest knowing that. 

You dove anyway. *hugs*

Whatever decisions that you are gonna make, just be sure u wont regret your choice. I risked it once and got my heart broken, it really hurts, a lot. At that point of time, i regretted the choice of stepping into that r/s and I swore to never let that happen again. But now thinking back, when everything's over, that choice was not a mistake nor a regret. It meant something in my life. Changed me, and I grow up from it. If I had to do it again, I would make the same choice. 

NEAT POST,

@verified_but_still_denied - I understand what you're saying. Sometimes, I wonder to myself if I would be able to maintain a relationship if I get into one now, and while I think I might not, I also tell myself that I should be able to prioritize so that I can make time for the relationship to keep it healthy. As for worrying if something would go wrong, if you do keep worrying, something will go wrong not because it was meant to happen, but because you are forcing it to happen by worrying about it happening; in a sense, you would be the one creating the problem. One of the ways I would deal with situations like these is to not get riled up about something if it is not affecting them. If only something is of concern, they will come to you or you can go to them and communicate. Otherwise, if no one says anything and something does happen, then communication would be the thing to work on. Just remember, if you keep thinking something will happen, it will. The idea of that law is that despite it not happening yet (or if it will), you're putting yourself in the mindset that it will or already has happened. So, sounds cliché, but go with the flow of things and adapt as new things come up. 

@verified_but_still_denied - it would help if you picked up the phone =p

@Yohkom -  That is a small problem of mine...