I'm not buying the whole Cinderella story angle that Halloween is a trans holiday because people don't care what you're dressed as.
1) That implies that it's only 'valid' to be a gender minority for one day a year. Imagine if you said that gay people had to confine their homosexual activity to Pride?
2) They're still going to care the next morning.
3) For me, it almost feels like people are mocking me. It's like 'yeah, being you for a day is fun, but I wouldn't want to live your life.'
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I wouldn't use a 1984 metaphor to describe how all this constant examination feels. It's more like being an ant being studied by entomologists, or Slaughterhouse Five.