Drifted apart from two really good buddies I'd hung out with for many years back in my high school days. In one case it was kind of a personality burnout, we hung out so much it eventually got to a weird point where we couldn't stand each other. In the second case my buddy was changing a lot and I was in a very weird, rough patch in life. I regret how that second case went down especially. Nobody was trying to be an ass about anything in these situations but they just gradually developed to the point where I, especially, was acting like an ass. I've never really seen either of those guys since but I sent them both an awkward email apologizing for how stuff happened like a year or two later. First guy responded positively, apologized himself, and it was cool. Second guy never replied. It sucks, man, but it's a part of life. What happened with your bud? (It's cool if you don't wanna get into it.)