if they have a gen one pokemon keychain, backpack, sticker, plush or whatever on them, don't bother; you arent get an interesting conversation, let alone friendship, out of them as a pokemon fan
if they have literally, i mean it, ANY other gen's pokemon merchandise on them, you will likely find them worth your time and you might even make a friend or two
I dont say this because "KANTOOOOOOOOO" or whatever, but it's pretty much 99.9% likely that if they have any/only gen 1 merchandise they're likely just being trendy and you'll just end up embarrasing yourself if you talk about pokemon beyond gen 1 to them, hell they might not even know other gen 1 pokemon like vileplume or kangaskhan if they only mention charizard or pikachu
at least you'd have a chance at socializing with somebody who has something beyond the "surface" of pokemon