Huh, could've sworn I posted in this thread months ago.
First Pokemon game was Red back in 1999, back when I was 5 years old. I still remember the big Pokemon craze taking over pop culture in 98-99, so I was quite familiar with a handful of the original 151 before I ever got the cartridge myself. What finally convinced me to ask my parents for the game was going to a friend's Pokemon-themed birthday party, where all the guests got a little bag of nick-knacks and candy. I remember getting a little cheap tape-measure modeled after Poliwhirl.
Of course, me being barely able to read at the time, I had quite a share of derp moments playing through the game. Took me weeks to find out how to leave the house, took me several months to make it past Viridian Forest because I didn't know how to save the game, and I even had to restart the save later on because I only trained my starter (Squirtle), and ended up trading it for a freshly caught Magmar. RIP.
For some reason, I didn't pick up and play Gold/Silver until around the 2006 holiday season, so my next game after Red was Ruby. That led to even more facepalm moments, like not knowing what to do with the Wynaut egg, or freaking out and shutting off the game over seeing a Shiny Pokemon, thinking my game glitched.