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AlfredoTurkey said:

This means that when the first Pokemon craze hit the US, I was roughly 19 years of age. This meant that I would completely miss out because, you know, image, girls... you get the picture.

I know, I've been there xDDDD. I feel very stupid right now, because I missed some great games just because of coolness. It took me a while to admit that I'm not cool and not designed for the popularity, and I prefer to play Pokémon at home than go out on dates and parties XDDDDDD.

OT, I think you can start with the new ones (X or Y), since you have Pokémon from each gen, and then, if you're interested in a particular gen, move to those games.