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Gen 1: discovering that for some reason I could solo giovanni with an ivysaur by spamming solarbeam the whole time. For some reason he only ever used growl, tail whip, or some variant
Gen 2: Discovering Suicune existed. "Well I mean this is like the 5th Entei I've found, if I faint it and get the massive exp from a legendary then I'll just find another one." Running into Suicune that same day I thought it was the angry ghost of Entei
Gen 3: Catching a Ralts after a day's worth of effort. I hated that wally caught one before I'd even seen one for the first time
Gen 4: Taking out the league with a Deoxys my friend hacked for me in Ruby. Yeah it's stupid but I loved that alien
Gen 5: Catching Victini and making it part of my first ever Gen 5 team. Making a simple legendary like Victini available early one was a great move on their part and I wanna see them do it again
Gen 6: Catching a shiny Budew 30 minutes into the game, my first legit shiny ever