Pokemon X/Y

[Vampyr]

Originally Posted by Angrist

I'm a few generations behind! I just might start playing Pokémon Diamond.

I would say skip Diamond and play either Black/White ( 1 or 2, doesn't matter) or HeartGold/SoulSilver. Both of those are pretty decent upgrades over Diamond/Pearl. Specifically, Black/White let you use TM's as many times as you want. HeartGold/SoulSilver has an amazing PC management system and you can have a pokemon follow you around on the screen. Not to mention the world is just huge and it has that nostalgia factor.