I Realized I'm In Love With A Friend After Years, Should I Talk To Him About It?

[InohDiskts]

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.

[Old_Geezer]

Tell him if you wish, but don't get your hopes too high. You seem to have slipped into a good friends scenario so there's a reasonable chance that the possibility of a romantic liaison has slipped by. So don't build it up in your desire for the future, tread carefully and see how it goes if you casually mentioned that you've feeings, if you do decide to do so.

[enfable]

Why don’t you arrange to Meet up one weekend, there’s a bank holiday in August. You could test the water by saying something along the lines of ‘I wonder what it would have been like if we’d dated’ and see what his response is.

If you do not approach the subject you may end up regretting it for the rest of your life.

I don’t regret doing things I’ve done only things I haven’t.

[Ringlet]

Catch yersel on!

[BagPussAA]

I think enfable's advice is very good. Go and see him around the bank holiday when you can spend a day together. Tell him how you feel. If he is a good a friend as you have indicated then it wont affect your relationship even if he doesnt feel the same. It might just bring you closer as friends. You indicate that you can talk to each other about everything so... go for it and tell him how you feel. You will only regret it if you dont.

[Bobbisox1]

Not sure I understand the 'our way of showing affection'
What is your way?

[GymLadTim]

My advice is to seize the day and just call him and tell him how you feel. Life is too short not to tell people how we feel.

[mibn2cweus]

I'm no expert on romantic relationships but I wonder what would happen if you just came out and let him know precisely the nature of the relationship you would like to pursue should he happen to share your interest?
Seems to me a waste of life worrying that you might lose something that was never there to begin with.