I think I kind of understand what you mean, but your similes don't really make sense. Far too old to be a Twitterer? Donald Trump would beg to differ. Quake (1996) and Half-Life (1998) are also not far enough apart to be generation-defining. In the end, if you fail to be accepted by a community, you can always find reasons for it, but you can never be sure if you're correct about them...

BTW, I find this (mostly) American tendency to divvy up people into strict categories by their age very strange: boomers, gen. X/Y/Z, millennials etc., each with their own stereotypes. Which leads to even more alienation when people look at these (and other) stereotypes and think that they don't fit in because they don't recognize themselves in them. Of course they don't, because every person is unique!