HOW I SEE THE MAIN DATEABLES EXPERIENCES WITH THEIR GENDER (my own headcanons, me being silly)
Karen: I believe she doesn't exactly feel like a woman, not in a trans way, but in an autistic way. All of these feminine things and gender labels don't make sense to her. She knows she's a woman, but she doesn't have that same connection other women do. We don't know when she got her diagnosis, if it was late then that'd explain why Karen would feel different from the rest of girls since she was young, why, despite acting like one, she doesn't feel entirely like a woman. (I could be projecting at some extent). Still uses she/her
Oliver: we know he canonically is a trans man, but what if he was transmasc? A version I have of him is a super masc looking, but not exactly a man. While Oliver was transitioning, he said Dickens taught him how to be a real man, leading him into having a toxic masculinity mindset for a short while, perhaps due to dysphoria or insecurity, or both. Later on he relearns we all should do whatever we want whenever and be happy and reconsiders his gender once more. Perhaps deep down Oliver doesn't identify as a human, and more of a secret fourth option, but still likes using masc clothes, labels, looking manly, etc. I don't want to label this experience of his, FOR NOW, but he doesn't mind it/they pronouns used on him
Randy: trans woman in denial (uses he/she....FOR NOW). Because of how Randy was raised, he never had a room to experiment with his gender, and every time he brought that to the table, the conversation was completely denied and his family judged him harshly. These feelings and identity have been buried deep down for years and years. As far as I know he's not religious, but perhaps had some guilt for having this wish and seeking freedom, kind of seeing it as some form of sin, and his family's influence strengthened that. Only after Gingi meeting Randy, he realizes people truly care for him and as much as he's scared of being laughed at again, he opens his heart. Can't see randy having surgeries nor changing her appearance much, outside a couple of more feminine outfits
