Have you ever experienced something so unpredictable you questioned reality?

yes often

Yeah. Usually it involved people doing things I never expected them to do and made me change my whole preception of humans in general

Everything about this world is so wild, how could I not question it every second that I spend in it?

Trump winning the election was the only individual situation that did that to me.

Everything happening with Trump's administration makes me question reality, the sanity of my countrymen, the Constitution and all I was told that my government supposedly stood for.

Absolutely. It was more my own sanity, though. It was bad for about 5 minutes.