I can understand why trans vriska and trans june egbert are incongruous and certainly also pretty damn cynical. It is way too easy to categorize these reveals as post-canon attempts to earn Woke Points, which may or may not be the case. I can certainly see it with Vriska because I don’t have a strong emotional connection to her nor do i think it goes against anything she has ever done or said in the comic.
June however I have a problem with, because John was always a prime example of non-toxic masculinity. He was a boy who loved his dad openly, and his dad loved him back. He baked with his father, he played rough with him, he was excited to wear a grown up suit just like his dad, he modeled himself to his dad and in turn he became the prime source of emotional connection and the heart of the team. He was a very powerful representative of a Boy who is masculine, but SECURE in it to the point he doesn’t struggle with his identity in the comic but rather acts as a bedrock for others. He was, ironically for a character associated with the wind, a stable and nonjudgmental fixed point, who could reach out and pluck his friends away from dark paths. He did this with Rose, he did this with Dave, he did this with Jade. He encouraged them to believe in themselves and love themselves, because HE loves THEM. This portrayal of masculine-flavored friend love was a huge part of my concept of the character, so it’s tough for me to imagine June could be a plausible iteration of this hypothetical person who exists in my mind.
Eridan may not be trans, because I agree that jumps the gun. He is at the very least a questioning person who needs to do soul searching and self reflection before coming to a conclusion. In my mind, it’s likely that he will conclude he is still a boy, still wants to be referred to as he/him, but he happens to enjoy being a fabulous crossdresser and being a gender nonconforming badass no matter what anyone says. GNC is probably a label that suits him best, but he’s a fictional character.
There’s also the fact that sometimes gender and sexuality headcanons are purely wish fulfillment. There is nothing wrong with that. We are talking about people who only exist as pictures and words on the internet and a system of memories and personality that exist within our minds. They are real because we made them real, and there are infinite ways you could discard or warp or turn over or copy the character you have in mind to make yourself happy. It is a valid thing to do, because nobody is getting hurt, and it makes the one making headcanons happy.
It is different for a creative team actually connected to the source material, because these are supposed to build upon all the rules stated before. When you put out a work publicly, you come up with rules for the world the characters live in, and part of the fun is imagining and pretending that these people are real and had a life before the events of the story. Unfortunately, once you put something down explicitly in the work of art you made, the expectation and good storytelling form dictates you stick to the thing. In the words of a youtube reviewer, the audience attitude is this:
You came up with these dumbass rules and I expect you to follow them to the letter.
Now there can be some wiggle room. You could keep a part of the story deliberately vague so you don’t have any solid rules to break. You could keep something a secret and not reveal it until much later on, creating a shocking swerve and make an unbelievable plot twist that changes everything. You could introduce the superpower in-story to change reality so that any errors never happened. You could end the story entirely and then reboot it, this time with a clearer idea of what happened and what didn’t within the context of YOUR story.
When you try to say “actually this character was always secretly X the whole time!” That gets frustrating, because it breaks the rules in a really lazy way to get all the benefits of getting the audience’s attention but at the detriment of audience goodwill. This is why Gainax Endings piss people off so much. If your deep and deconstructive mecha anime ends with the main character talking to a penguin, you get angry people demanding their questions be answered. If you suddenly reveal that Dumbledore was gay the whole time, it’ll be hard for people to take you seriously and it will make those who wish for more gay rep outside of stereotypes really mad because it’s a toothless, shitty reveal.
If, as the result of a lottery, someone wished for the main source of healthy masculinity and stability were to become a trans feminine woman, and God grants that wish but makes no effort to demonstrate it anywhere, in any of the media revealed so far, and won’t even show it in the Deliberately Shitting On Canon Pesterquest... well. I hope that the transition and explanation for June Egbert shows up sometime soon.
In real life, June doesnt need a “reason” or to “explain herself” of why she is herself. But June is not real, and all evidence that the audience agrees is true points away from June being a thing. Unfortunately, I am attached to John, so June will need to give me a lot more convincing before I start to feature her in my stuff. That’s really the extent of the debate, though. I like John as he is. I’d rather keep him around for all he means to me. That’s just me personally though. I have no right to demand others do the same.