My brother was five and I was six when he got Yellow Version and a Game Boy Color for Christmas. (I got Furbies or something... idr). Neither of us had touched a video game controller or handheld before, but that moment basically got us hooked. A childhood-defining moment, I guess. We played through it together. We struggled so much with Brock, I still maintain Yellow Brock is harder than GSC Whitney (unless you think of getting Mankey, I guess?). Then we went to our grandparents' and my three or four-year-old little cousin restarted our game, so we had to restart it and do it all again T_T We used a Pidgeotto to do it lol, always. We don't play video games together anymore, but until I got my own GBC and Crystal Version, we always played Yellow and Gold.
I remember I was so terrified facing down Champion Gary, the pressure was immense and the music scared me, and when I finally beat him I felt the most overwhelming relief. Then the credits played and it finally went black and said... THE END. So I thought the game died or something and we'd never be able to replay it. I almost cried with joy when the game restarted and I could play it. ^_^
Mt. Moon was hard... people in the school playground were all stumped trying to get out of it lol let alone Rock Tunnel.
Sadly my brother's Yellow Version stopped working years ago, so my brother actually bought a new one from eBay and replayed it heh
I really loved RBY, but I have so many memories of GSC as well. A lot of you might have heard this story but there was this kid at school who wanted my beloved lv. 70?ish Politoed, and offered me a cloned lv. 100 Dragonite. Well, trading wasn't big at my school and I thought that Dragonite was so damn badass, so I did it. Then I went home and missed my Politoed and cried my eyes out. I rushed to find him during lunch the next day and begged for the Politoed back. He agreed and I got to keep the Dragonite too since it was cloned. It has been claimed that my Politoed was cloned, but look, when you share a bond with your Pokémon, you know these things...
I used to totally own my brother with that Politoed (it knew Hypnosis) over link cable.
Good memories of the TCG as well. Said kid didn't want his trading cards anymore so he smuggled bundles of them into the playground in elastic bands and hairbands and whatnot and split them up between my brother and me. I still have a million Grass Energies from that. We didn't own a rulebook or damage counters or anything, so I made up the rules as I went along (since I was also a disgusting little cheater as a kid lol) to suit me. Like oh this card has a higher Lv., so I get to attack first. Then if my card had a lower Lv. than his, I'd say this Pokémon is OBVIOUSLY faster than that Pokémon, or it has more HP, etc. etc. And if we wanted a card we'd just look through our decks to find it. I bought one of those official decks during the EX era and tried to teach my brother but he didn't like playing with rules and ragequit.