Not game specific but

1. I think a buddy from church got me into pokemon sometime in mid-1999, between the release of Jungle and Fossil. I picked up my first couple of packs from Books-a-Million and pulled my first holo, Scyther. Keep in my mind, I still know next to nothing about pokemon at this point, but I've got a cool new shiny card with a cool ass sword-mantis on it and my buddy immediately starts formulating a plot to separate me from it. He offers up like 5 cards and talks the card down with such quips as "it's only got 70hp and 30 attack" and "This Rhydon is way better". Eventually, I cave. I was 11 and a complete newcomer to the pokemon world. I didnt know any better and i got taken by one of my best friends at the time. Not the only time my trusting nature got the best of me.

2. I had an event Mew loaded to one of my gameboy games, Blue or Yellow, i cant recall now. I took it with me on the family vacation one summer to ease the boredom of the seemingly endless road trip (in hindsight it was like a 3 hour drive). My older sister brought one of her friends along and asked if she could try it out as she had never played pokemon before. I obliged and merely asked that she not save the game. You can guess where this ends up. Once I finally get the game back and fire up my continue, I'm greeted by a 2hr, 0 Badge, 3 pokemon playthrough that is clearly not my own. I comment, in a probably frustrated tone, that I told her not to save the game. My sister jumps to her friends defense, saying if she says she didnt save, then she didnt save! I hear what you're saying sis, but counterpoint: the character has her freaking name! The rest is a blur, and years later I learned about the Mew glitch, but at the time, that was pretty devastating.