It was 2004.
I believe I was around 9 at the time. That seems a bit too young for me to start something like this but my Grandpa was the one who introduce me to it.
At first, I was horribly bad at it. My Grandpa even gave me a magazine for it but unfortunately, I was too young to understand what was in the magazine.
I just played along, trial and error, until I beat it. In fact, I remember it took me about 176 hours to beat it but even then I was still far beyond from becoming a master. But I never gave up.
Over the years, rather than quitting, I continued to get better. About a decade later, I was almost a master. I even taught Luis my skills. Unfortunately for Luis, I had to be the master for him. After the torture and brutal lesson I taught him, he finally learned and was ready to join with me to the stage against the world. We never became the stars we were meant to be but at least we're not amateurs anymore.
After our glorious attempts to be stars, I decided to retire due how the series had become. Maybe in the future, I could be willing to try again.

And that's how I got into the Pokemon series. My Grandpa one day gave me Pokemon Sapphire that came along with a strategy guide (along with other games). I wasn't able to understand how to read the guide but I just kept playing the game through (countless) trial and error. I remember starting over several times because I didn't know how to save the game (mainly overwrite save data) and didn't know how to progress in the story.
I remember having a Brave nature Treeko which eventually evolved into Sceptile by the time I got my third badge. My Sceptile literary fainted several times over and over until he over outleveled other trainers' Pokemon. I didn't even know how to catch or use other Pokemon until much later in the game. Even then, I never used other Pokemon for battle. I used them for HMs but never for battle unless I had to revive and heal Sceptile. Did I at least capture Kyogre? You probably already knew the answer to that. After so many hours of trial and errors, I finally made it to the Pokemon League. By this time, Sceptile was already Level 100 and everyone else was Level 40 to 50ish. I fought my way through the Elite Four (using Sceptile mostly) but was eventually stopped by Steven completely. His Level 57 Skarmory alone was enough to stop my Level 100 Sceptile. Sceptile had nothing that could beat Skarmory and by time I could wear down Skarmory, the rest of his Pokemon (mainly his Metagross) finished my Sceptile and the rest of my Pokemon.
I gave up for a while and eventuall found TM02 Dragon Claw. It looked powerful so I decided to teach it to one of my Pokemon. I was surprised that Sceptile could learn it. Do you know what move I replaced Dragon Claw for? I replaced Dragon Claw for Earthquake. That's right. I replaced a move that wasn't effective against Skarmory but was effective against the rest of Steven's Pokemon.
After some preparations (buy revives and full restores), I began my assault against the Pokemon League. I tried my best to save enough Dragon Claw PP for Skarmory and I did. Unlike attempting to beat Skarmory with Leaf Blade or Giga Drain in the past, I used Dragon Claw. It still wasn't effective against Skarmory but it was more effective than using those Grass Type moves. Finally, I got to his Metagross. I couldn't use Leaf Blade or Giga Drain anymore so I was stuck with Dragon Claw. Guess what happened? I won. After 176 hours of play time, I finally beat the Pokemon League for the first time. Despite all those ungodly amount of trial and error, I still kept playing Sapphire.

It was like this, minus the Mega Evolution.

As time went on, I slowly became better at Pokemon. I learned type matchups, learned how to use other Pokemon (in fact I got a Salamence and Metagross), and even beat the Battle Tower 50 times in a row with the same Sceptile, Salamence, and Metagross. I even got my Grandpa to get me Ruby. I did much better in Ruby since I had more experience now. Eventually, I got Emerald and FireRed. In Emerald, I was able to get all the silver emblems from the Battle Frontier. In FireRed, I beat the game without a strategy guide or any knowledge of Kanto other than from the anime.

Then Gen 4 came. I convinced my Grandpa to get me Diamond and a DS Lite. I was able to beat the Sinnoh Pokemon League but I had trouble finishing the Sinnoh Pokedex because I had no idea how to get Drifloon. I even convinced my Grandpa to get me a strategy guide and I learned Drifloon can be obtained on Fridays. Yes, I convinced Grandpa to waste $20 just to figure out how to catch a Drifloon. As Gen 4 went on, my knowledge on Pokemon didn't improve other than learning about the Gen 4 Pokemon. At some point, a butthole in middle school stole my Diamond and I bought Pearl from a friend a few weeks later. I never got Platinum or HGSS because Grandparents destroyed my DS Lite for disobeidence.

Eventually, I got a DSi and Pokemon Black. I also found my Pearl from when my DS Lite was destroyed. Still no improvement on how I played Pokemon other than strictly catching Pokemon using a regular Poke Ball (even against legendaries).

However, around 2014 was when I improved in Pokemon. I learned about natures, effort values (EVs), and individual values (IVs). That's when I began experimenting on creating competitive Pokemon in Pokemon Black. The Pokemon I bred had the nature I wanted (usually Adamant or Modest) and 3 perfect IVs at best (Destiny Knot didn't have the breedong effect yet and I relied on Power EV Training items).

Then, Gen 6 came. When the 3DS came out, I didn't want to get the 3DS until Youtube was possible and Hoenn is actually confirmed. When ORAS was announced, that's when I began to save money for a 3DS and AS. I got AS on launch day (Nov 21, 2014) and a (used) 3DS a month before. Using what I learned from Gen 5, I was able to breed competitive Pokemon and I entered the competitive scene for the first time. However, the way I played Pokemon changed forever. Every time I obtained a Pokemon (especially legendaries), I made sure it at least had the correct nature. I would soft reset over and over until I got the correct nature and hopefully the IVs I wanted. I could never play Pokemon for fun anymore. Everything I do now in the series was competitive and trying to get the perfect Pokemon.

This is my history of playing Pokemon. How I went from being such an unimaginably bad noob that would make Twitch Plays Pokemon look like an MLG feat to actually being able to play Pokemon in MLG (or VGCs) and make a battle video of sweeping a friend's entire team with a single Dragonite then uploading said battle video to an adult site (probably got takem down by now).