I love this premise. I remember reading a book along the same lines where all the characters were the same person across multiple universes. Using different "you"s is a great way to have a diversity of opinion while being applicable and non-confrontational when dealing with personal questions like this come up. Also seems like a good introduction to gender identities, and how one could discover their own feelings towards them. As for nitpicks, the messages come a bit fast at points, and scrolling back isn't an option until the flood stops. Also, the scroll bar goes under the header so that's a thing. But those are pretty minor criticisms for a fun little self-exploratory story.