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So I was browsing the favorites of an artist I recently discovered and noticed among the favorites was recent artwork done by a person I was acquainted with back during my high school years. Said person seems to have become semi-well known since I last saw them, but it feels super awkward to come across said person again after all these years because our old friendship didn't end on good terms (I heard he even even broke up with his then girlfriend not long after the two of us stopped talking).

Also about a year or two ago I checked on what became of a page on an art site I abandoned long ago, and was surprised people I knew from that time in my life still occasionally left "hey dude, where'd ya go?" messages on the wall. One of those people even being someone I used to know outside of the internet as he and I live (or maybe "lived" at this point, hell if I know if he still lives around here) in the same city.

Adding classmates to your Friends List tends to do that. It's almost as if they no longer want to associate with me. . . Well, it wouldn't be too far from the truth, honestly.

Well of course it's gonna feel awkward most of the time. As we go on in our lives, we take different paths. I'm pretty sure if the people I knew in high school found out about the kind of person I am now, there would be all sorts of awkward banter. And the same is for the people I'll meet in the future like that. It's just the way it is.

Honestly I think it just shows your evolution and development as a person, and in a way it's "growing pains" so to speak.

In my case is more awkward since some became part of gangs in my city.

Yes especially when the relationships end awkwardly and abruptly. I try to avoid interacting with real people on social media at all costs, and to be honest it usually just shows me a side to them I'll probably hate and I'd rather avoid it.

There's also meeting old online friends again which is less awkward but it a similar emotion and process.

No, not really. Then again, I've never really had a plethora of friends to begin with, so that could be part of it. That and there's really no way for me to know when I come across an old friend, especially on a site like this where everyone uses a username and an avatar. The fact that I despise social media also contributes.

Now if you're referring to people that I've met online, well then I guess not. I used to get myself into awkward situations online on occasion, but I like to think that I'm beyond that now.