I think the concept of a story about a character going through the early stages of his transitioning is really fascinating and does fit in with the whole rebirth theme of this game jam. The execution itself was pretty good if not for a few caveats. The dialogue can feel pretty stilted at times. For example, it's a tad awkward for the mother to come into the scene just to say, “You’re still going on about this gender stuff?” unprompted with no context why she said it in the first place. A lot of the dialogue follows a similar format to the example I provided. I feel like if the characters had more of a (pardon the pun) transition into their lines it would feel a lot more natural.
Aside from that, the writing is good, I can see it striking a chord with other trans people who see themselves in Oliver. The soft background noise is also a nice touch as it makes you feel like you're part of the scene. One last thing to note, the art style of both the characters and the textbox clashes a bit. It's odd seeing an RPG styled text box in a heavily illustrated game.
Overall, a pretty nice game with a sweet story.