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i think one of the best momments for me was way back in 2017 when i was making my first playthrough on the neutral route. I had little to almost no computer knowledge back then so when flowey simply crashed my game i got so scared that i didn't touch my save for at least an entire day
art source: https://www.tumblr.com/9twoeight
I (like many others) accidentally killed Toriel and reloaded the game. When Flowey KNEW about it, I was totally freaked!