When you like someone you want the best for them, someone who has a low view of themselves will think that they aren't what's best ,and will believe, sometimes with reason, that others see them in a bad light.
It's easy to say "don't worry about how others look at you" when you're from a high...
You just earnestly talk about how the way the work approached and developed certain themes impressed you, then you show scenes that left a big impact on you.
Stop that. Don't limit what people can and can't think, do or be.
The goal of gender nonconformity is to make society a more accepting place, to give people the permission to be what they want to be, without having to care about others judging or trying to force them in small boxes.
Some people...
Many men want to be Moe girls, not because they're trans, but because they think that life would be easier if they were cute. Naturally a scary looking guy who doesn't have friends and love Yuri would believe that being a girl is better than being a boy