I had a Game Boy but when I saw a friend's Game Gear I wanted one *so* bad. Had to give up my Game Boy for it. I guess I mostly regret that choice, but I did also have a lot of fun with a handful of Game Gear games.
C64/DOS games at my cousin's house, and then Mario Bros./Duck Hunt on another relative's NES. Died right away but I was hooked My folks bought me an NES shortly after that first experience with Mario.