How I started playing Pokemon:
Just before I entered high school, my brother and I were still subscribing to Nintendo Power and checking out previews for upcoming games. During this same time, the toy craze was to get virtual keychain pets, so we tried Tamagotchi. Pretty fun, but kinda lame, so my brother got a Digimon keychain, but that still wasn't what we were looking for. When we read about a new game, called Pokemon, coming out for the Gameboy we thought this would be the best of them. Raising critters to battle with, and we didn't have to clean up their poops.
After school started I wound up in a circle of geek friends and many of them wound up being fans of the funny new game too. One (who is now my boyfriend) spoke of creative ideas on how to use the TM items, such as teaching Haunter Counter and Fissure, or how powerful Gyarados could be despite spending 500 for the Magikarp. Unfortunately, my other friends discovered cheat devices, and I lost interest when all they wanted to do was make teams of six Mewtwo. In this way, I lost the point on why breeding was awesome in Gold/Silver, and lost interest in series entirely when Silver's story was pretty lame and the new Pokemon hard to raise without breeding.
How I started playing Pokemon again and found Smogon:
A few years later, I rediscovered the handiness of having a Gameboy when traveling on the bus to work and school. Thinking it'd be nice to have a long game to play with, I decided to pick up LeafGreen since I always liked Grass types. Trying to remember how to do this and that, I simply went to GameFAQs where I usually go for game tips and found blueshirt32's and strawhat's moveset and teambuilding guides. They were very fun to read, since I wasn't very familiar with all the Pokemon yet, and it was fascinating to read on advice that spoke "do this if you'd like to win".
I mostly used the guides at first as a reference to how to build my in-game teams in LeafGreen, and later Ruby. My Ruby team consisted entirely of Pokemon I thought were the weirdest, but it was rather helpful to know that giving Exploud Shadow Ball was a good idea in case I ran into Ghosts.
As I became further interested in this "metagame" they were yammering about, I decided to figure out just what this "Smogon" was that these ideas came from. I was far from being able to play a multiplayer battle and didn't even have the right operating system for NetBattle; however, by the time Diamond/Pearl was available I was able to comprehend enough about how the game worked to hold my own in WiFi.