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Dumbass Pokemon moment from my youth: When I first played Gold/Silver (gameboy color), I misunderstood the rival's name presented as ??? to be a mystery that would later be revealed. When the professor asked me what his name was, I entered ???, thinking there would be some cool reveal later in the game. My siblings also had the game and named their rival, and while that should've made me realize my mistake, I stuck to my expectation. By the time I got to Lance, I fully realized my mistake.
I don't know if it was the game's font or I really had a derp moment around that time because another thing that puzzled me was when saving, the game appeared to say "DON TURN OFF THE POWER" and I'd wonder why the game was mentioning a Don and telling them to turn off the power because 'wouldn't that be counterproductive to saving?'