Me and my friend know each other for about 4 years now. We met in High School, and we always had a very special connection since we met. We both had a crush on each other, but at different moments, however, since we never told each other at the time, nothing happened between us, he thought I couldn't possibly like him, and I tried to tell him, but I got so nervous that I messed up and he understood something totally different.

We both moved to the South of the country for college, and now we always return to our hometown to spend Christmas with our respective families. Last year, we got to see each other for about a week, and ended up discussing how we both had a crush on each other during High School, but we had little time, so we didn't dig deeper into the subject. As soon as he left though, we began texting all day, every day, until our classes began. We usually talk every once in a while, sometimes we can go without talking for months, but every time we do talk, it's very special and meaningful, on holidays we usually spend the night on a call. I trust him very much, and so does he. We frequently tell each other things we usually don't tell other people.
Over the course of this year, we've both been in failed relationships, and discussed them with each other. We both share some difficulties when it comes to dating, people usually don't understand our way of showing we care, we frequently don't know what we're supposed to do or what the other person expects of us, and we overall just feel too awkward about it.

I hadn't thought much about him, until some time ago I realized he was one the few people I didn't have to be constantly talking to for them to know I care. I also realized how much I trust him and how we always got along so well. Then, over time, I realized I'm in love with him. Thing is, what to do now? I want to tell him, but I think it might be better to do it personally, but for that, I'll have to wait until Christmas this year. Not to mention that he's not in a relationship right now, but what if it's too late if I wait until Christmas?
Also, in the beginning of this year he admitted to still having some feelings for me, though he didn't make it clear if it was more of a "friends with benefits" kind of feeling, or if it was more like something to build a relationship on. Not to mention that was before he got into those relationships this year, so maybe he doesn't feel the same anymore. In any case, I can't be sure unless I ask, but should I? He's one of the best people I've met, and it would be kinda sad to lose him, if telling him how I feel would destroy our friendship.

Friends should be able to talk honestly, so talk now and lay the ground work. Just bring up the subject of dating and as a caution, leave the sex out of it until you are very clear romance has a chance. See what he says and keep it real (No expectation of romance). Give yourself the chance to find out if this friendship can stand the rigors of romance, or is it just a band aid for wanting romance. Or seasonal lust not at all unusual with friends between romances or just coming out of one.

Dating is about having fun and getting to know a person and seeing if the risk of building more is possible. Is it possible your feelings for this friend is just a safe secure place to be during a hard time in your life? You're feelings are so normal for a person, let me guess, a person without enough social activities outside of family and few friends and work or SCHOOL.

That alone would make your friend all the more attractive. Hard not to build a fantasy romance in your head that has little to do with reality. Find that reality by talking honestly NOW, but you should be actively building a life that you enjoy with friends and family and activities that make YOU happy without him. I mean he seems to be actively dating others and doing his thing, and I wonder are YOU doing your thing?

Please clarify since this is about YOU. Got close female friends? I think it a healthy thing that people date and have fun before they decide to pour their hearts out. You don't really know a person until you interact with them on other levels besides the phone or social media, or the occasional in person chats.