I started playing pokemon when it first came out in North America. I was 14 at the time. My friend and I bought it the very day it arrived at the local gaming store and we traded cartridges. I played the Red version.
I remember getting the Game Boy Mini, just because the original big clunky Game Boy was too big - hence conspicuous - to carry around at school, and I wanted to play that game every chance I got. I earned a lot of money doing other kids' homework, just to get the game. I traded many pokemon, won many link battles, lost many link battles, hunted the mysterious Missingno, sought the elussive Mew, and lost several game saves in the process. Eventually, because I brought my Game Boy everywhere, it was stolen, and I was distrought over all those poor lost poke-souls (not to mention the countless hours spent acquiring them).
Eventually, I got a Game Boy Colour; and when pokemon Yellow came out, I gleefully got that too. It's funny, because at the time I was impressed with the colour that was added the game; it's almost like looking back into the dark ages of gaming. That game kept me sane through a troubling time in my adolescence, and I still have that cartridge to this day. However, the only person I ever let borrow it was my girlfriend at the time - probably because I really trusted her, but most likely because she was a pretty girl and I was a teenage boy.
Eventually, Gold and Silver came out, and that was special because they were full colour games. In fact, it marks the only time (if you don't count the fact that I owned the blue version for a few minutes) that I bought all the versions in a generation, Crystal included. By this time I had changed schools, so no one I knew played the game; despite this, the game was never too uncool to play. Actually, I played the games so much that they were taken away from me by my father and I actually devised a way to go down to the United States and retreave them.
I bought Sapphire, Leaf Green, and Fire Red, and survived the lowest point in the game's generational shift. I still enjoyed the game... but eventually, I stopped playing out of bordom, and disappointment over the fact that I couldn't transfer all of my favourite pokemon trapped in the Gold, Silver, and Crystal cartridges.
...And then, Generation IV hit the market and peaked my curiosity. I bought the Pearl version and played it with a newfound love of the game. Platinum was even better, and pretty much caused me never to touch my Pearl cartridge again (I don't even know where it went). All was good, and I was happy with the series once again; sure there were evolutions that I wanted to see, but if another generation never came out, I would have been fine with generation IV.
When Soul Silver and Heart Gold came out, I was overjoyed and bought those as well. In my opinion, the best versions out of all the games in the series. Though I like generation V, I find myself still going back to SS/HG, just because it is so enjoyable.
So, I have been with the game through the entire series (there are the peripheral spin-off games that I played as well, but those don't really count), and though I am now 28 (with 30 looming overhead like a dark cloud), I can see myself buying Pokemon games well into the future. As long as they make them I will buy them whether - they're good or not. It's not about how cool it is, or the level of gameplay involved, or even whether anyone else is playing anymore; because, at the end of the day...
Gotta catch 'em all.