Oooh, a lot. I got Silver at a particularly bad time in my life and it (and Red) were pretty much all I had at the time until I was able to access my things again. I remember playing it well after its hay day and still enjoying it so much because it just looks so nice. I still to this day think it's a really nice graphic style, especially the Pokemon sprites. A lot of my favorites come from gen II as well, aha.
Anyway, some of my favorite moments were doing the glitch to get all the starters, raising many Furret, evolving Eevee into Umbreon (still my favorite Pokemon and ofc I had no other means of getting it at the time aside from Colosseum, so having it in a handheld and evolving it myself was quite the achievement!), getting stuck in Morty's gym for a while (both the puzzle and the battle), and late summer nights in 2004 watching that weird summer camp show on Disney Channel and training my team to beat Red. I remember I beat the game completely for the first time around like midnight or 1 AM? Ahaha. So I like...had no one to share my joy with and then I didn't want to tell my mom I was up so late that night so...RIP. But yeah, I have a lot of great memories with Silver, and GSC as a whole, and continue to make them. I really hope these games make their way to the eShop!