I was initially very apathetic about Pokemon, being from a rather pacifistic family who frowns upon references to battling or fighting. However, my experiences in secondary school changed that, and I was more comfortable with the notion of battling/fighting (I was bullied in my one year there, before transferring out). Furthermore, my new schoolmates kept referencing Pokemon in school. Even so, I ended up keeping my apathy towards Pokemon until my final year in high school, at the tender age of 18. During that time, they used my ignorance to make nasty jokes about me by putting my Pokemon avatar in the school jacket as a Bidoof (It was too late to change it to a Gyarados once I found out what it is. Until Pokemon Dream World unleashed the Moody Bibarel. I would have opted for a Crobat nowadays.)
This is where things get weird. During that year, my graphing calculator had a massive FUBAR that required me to get a new one (It somehow managed to reset itself to normal afterwards. I now keep it as a backup). The new calculator is a TI NSpire CAS CX, the calculator you may remember as the one that can play GBC games if you visit 9gag. Since Pokemon was the only GBC game that I have heard of extensively, I decided to play it. I brought up the most advanced game that the GBC (by extension, the calculator) could support, Pokemon Crystal. Turns out it was a good choice. I later found out that the game mechanics of the original GB games were so messed up (to my standards) that I would have stopped playing Pokemon if I had started from Generation 1.
Pokemon Crystal was the beginning of my journey, and with all journeys, it is really messed up. I had absolutely no knowledge of the EV/IV system, and therefore I ended up only caring about type advantages. Many times in the Battle Tower there (I have never won a 7-streak once) I have ended up in defeat, caused by Pokemon there somehow tanking what my legendary team (Raikou, Entei, Suicune) could throw at them and managing to destroy them in one strike. This was the only version that I had actually used a legendary in the game playthrough (because I could not give two hoots about finding a Water-type Pokemon and teaching it Ice Beam, instead of using the Aurora Beam already on Suicune. I also like Fire-types, if you are wondering why I don't have a water starter).
With the end of Pokemon Crystal (having completed the Ndex, occasionally through questionable means), I moved on to Generation 3. I started out with LeafGreen, because I wanted to experience Generation 1 with more modern and familiar mechanics, then to Emerald. Emerald was the start of my strategics, though it kind of sucked. The motivating factor was Battle Frontier. I found out, with a handphone that could emulate GBA (and save states), how stacked the odds are against you the further you got in the Battle Tower, again using the legendary Johto beasts, even making 100% accurate moves (by right) miss at the most inconvenient times (by left).
Upon the advice of my friend, I move further on to Pokemon Platinum on a computer-based emulator. I found the updated mechanics better to use, and with it a new dimension in battling. Some Pokemon that were useless (to me) in earlier generations (like Gyarados, which has the typing but not the special stats to abuse it in Gen 3) became useful, and the additional new moves made it easier for me to hit hard off the bat. Despite being super effective in normal gameplay, my strategy is almost useless against other humans or more robust AI. I was very impressed by this new generation that I ended up buying a beat-up DS Lite specifically to play that generation. My first real Nintendo cartridge was Pokemon SoulSilver (my Pokemon Platinum was in flash cart because I could not find any copies left in any game store in my country); it was in a way symbolic because it was a return to the beginning of my Pokemon journey. I later bought White and White 2 (with the money I got from my holiday job), the latter too late for the worldwide Genesect distribution. I managed to get the Keldeo though.
I graduated from high school and became a military clerk (military service is compulsory in my country, and I have been deemed unsuitable for weapons and explosives handling). My first real paycheck ended up in my shiny new 3DS XL to connect to the WPA-secured WiFi in my house; it was worth every cent I spent. This also marked the further development of my tactical skills, with new Pokemon, new Abilities to abuse (that's why I am seeking those DW females in my sig) and new tactics. However, my tactical skills fall short of many of my contemporaries, single or double battle wise. (I ranked 7061st in the March VGC, half because my entire team revolved around single battles which I still suck at.) As to what the future holds, I remain unsure, but given that I am not so free nowadays due to my work, I guess things will have to slow down.
My age and maturity is starting to catch up with me, so I am starting to watch the anime (Japanese with Chinese subtitles; I couldn't stand the fact that Ash sounded whiny in the dubs) before I find the anime too illogical to continue watching. My current interest in the anime was also spurred on by the Shippers Community (namely the AdvanceShipping and PearlShipping communities) here, so I am watching the ones they are referring to first.
The most surprising thing about this journey was that what I just told you from start to now was only 1 1/2 years in real life.