Im in need of some help. I have this friend who I see as more than a friend but that's all we've been since we met. During our freshman year, he confessed that he actually had feelings for me back in middle school. I didn't know how to react at the time, but after some thinking I came to the conclusion that I felt the same. Some days later I brought it up again but before I could say I felt the same, he said that his feelings were something of the past and he didn't feel the same anymore. I felt shot down before I even started, and so I went with it. That he didn't feel the same anymore. Even so, he was the best. I loved talking to him, he was the only one who truly understood me. Spending time with him and talking were the best of my high school life. Deep down, even if we weren't a couple I loved him.

Time skipping to about our junior year. We were texting about how another friend of ours might've liked me. And at some point he wrote that about how he used to have feelings for me too but what got me was he ended it in a "who knows, maybe I still have those feelings." But despite what he said then we still stayed friends.

Senior year, I was dating someone else. Though I thought I liked him, we didn't have the same connection. I rarely even spent time with him. Throughout the relationship I spent more time with my friend that I did my boyfriend. And during those times I felt happier than anything. But I also had a lot of doubt with myself. "What if I'm over thinking my feelings about him?" "What if he still doesn't have feelings for me anymore?" "Have I been hurting him all this time being with someone else?" I felt so conflicted that I let everything be all the way until graduation. I broke up with that boyfriend and I've had the urge to spill everything to him, but we haven't talked since graduation. And I'm scared to death that my doubts will come true if I come out to him about my feelings. I'm terrified of being rejected for over thinking what I imagine what could've been all those years ago. Even more so...I'm scared of losing him, of hurting him in some way and messing up the connection we have now, even if it's just as friends. What should I do? Do I confess and see what happens or do I let it all go? I'd die before I lose him to anything, as well as my feelings on the chance he doesn't feel the same. So how can I get through this?

Well, it really comes down to pros and cons here, I suppose. If you can't find answers to your questions, your only option is to start asking new questions.

What's more important to you: having him halfway and being unsatisfied and conflicted but not at risk, or risking the relationship to have it all? If having him halfway for this long is leading you here, it's clearly still hurting you. But people live for that sometimes, don't you think? Without fear and pain, what do we have to maintain passion? We're all really so masochistic at the base of our actions. But, I suppose I'm getting off track, aren't I. It's clear that this is hurting you, which brings me to my next question:

Is the long-term pain really less than the shorter-term pain you'd feel from losing him? Is spending an indeterminate amount of your future being conflicted and unfulfilled better than taking a risk and moving forwards? Everyone thinks that the sting of rejection and loss will last forever, but 'love' is so rarely that powerful.

Lastly and arguably most importantly, can you keep doing this forever? Can you handle having half of what you want and never the rest for however long you two remain in touch? Because if you can't, the rest of the questions don't really matter, do they? Because that would mean that you know on some level that eventually, you're going to change your mind and take that risk anyway, so why not save yourself some time, cut out the middle man, and do it now while the odds are higher in your favor?

But I suppose that's just one point of view, after all. Personally, I've never understood the appeal of having something rather than nothing instead of having everything or nothing. Oh well! I've never been one to relate well to these things, either, so you might be better off listening to some more empathetic advice. Either way, I wish you luck and would love to know how this turns out.

Doubts are killing you? Then kill the doubts.
Talk open to him and tell him how you feel. Otherwise there will always be the ghost of the past haunting you and whispering "What if I had told him...?"
It´s better to live with a "no" than to vegetate with a "maybe", you know? You won´t go further this way, you´re running in circles like a cute, little hamster in a wheel. Don´t be such a coward - you only live once.

I think I messed up. I tried talking to him again and started off slow with some friendly talk but chose a bad set of words. Now I'm nervous.

What "bad set of words" did you chose? Perhaps it wasn´t that bad at all.

I was wrong. I did hurt him by being with someone else. I always assumed he was over me like he said, but i guess not. Looks like my worst fears came true. I hurt someone i really care about and now im barging in like i reserved a spot on his mind. Shit.