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1998: Joined the Pokemon craze, like everyone else. Was mostly into the show, and a bit too young to really get into/understand the games.
2000: NEW POKEMON!???? SAY WHAT????? My interest for Pokemon skyrocketed because the addition of new things made it seem fresh and exciting. Also started with the games here, which I thought was superior than the show.
2003: The introduction of even MORE new Pokemon was... interesting, but it was starting to get a tad old. The improved GBA graphics were nice, but I just didn't enjoy the Hoenn region as much as Johto. Plus this was the first gen where I thought they introduced some dumb designs. Interest steadily started dropping.
2007: Dropped Pokemon altogether, after seeing the horribly grotesque evos/pre-evos to some of my most beloved Pokemon. Nearly everyone I knew who played Pokemon also lost interest at this point. I thought it was going to be the death of Pokemon. The fact that I didn't get a DS upon its release also meant that I didn't try the games out at all.
2009: Was re-introduced to Pokemon through the concept of competitive battling, and fell in love with it all over again, mostly because of nostalgia's sake, and because I thought it was cool that a mere "children's game" could have so much depth to it. The gen 4 designs still bothered me, but competitive was so fun that I didn't care at this point.
2011: New Pokemon meant more variety in the competitive scene, so I was excited for this. Plus the new designs as a whole outshined gen 4 so much (though there were a few dumb ones here and there) that it completely rekindled my love for Pokemon.
2013: The added support for ease of competitive breeding/training (had to rely on RNG manipulation before, which was a bitch) made me play the games even more. This meant that more people got into the competitive aspect, which is always a good thing. I also believe that the addition of fewer new Pokemon was better for the series, and liked the Kalos region.