My first game was Pokemon Blue, when I was about 8 or 9. Then I got red, then Yellow. When Gold and Silver came out, I bought SIlver first, then Gold a few weeks later.
I skipped R/S, as the pokemon looked like something my little brother drew, picked up LG for nostalgia and then came back to Gen 4. I got pearl, and then HG, and SS. I let my girlfriend have my Pearl, so she could play with me (now she's obsessed, and also has my SS) So I got platinum. I recently went back and bought Saphire, though, I want to find emerald and can't find it in any stores.
I still feel like gen 3 is the one where they were lacking in originality, but they're still fun. I enjoy the region, if not the story/pokemon within it. It's okay, as I pretty much exclusively use 1st and second gen pokemon only.