[not sure if this is needed but very much spoilers below]
wow. I just finished the game and wrote like half a page of reviews on your tumblr before I remembered that I'm restricted by tumblr and my asks don't show up, got very sad that you didn't have any other social media available, and then remembered that this was hosted on itch.io and thus I could literally leave a comment here.
First off, Maddie's character hit so close to me, down to the conversation with the little girl. The fear masked by destructively pretending to be strong and tough was almost word for word what I went through and, to some extent, is still going through, and while reading this (at two in the morning in the dark, no less) I very much started tearing up. And this is probably my own personal reading of Maddie, made biased by me relating to her so much, but Maddie's experiences and fears felt so similar to that of the butch fear of pushing others away, especially lovers, by being too 'tough' and 'alone' and 'not needy'. (the fact that in one of the endings I got she magically gets a cool bike didn't help my baseless analysis, haha) The live show audience section really hammered in the whole 'tough performance' thing even more (again not to relate too hard and make a character that is not mine something she is not but it really really felt similar to the gender performance aspect of butchness to me ok moving on) and technical game-making wise, the jump from dark to glaring brightness really shocked me, well done. Almost felt like an actual game show spotlight as I was reading this in the complete darkness.
Moving on to a more literary comment, I replayed the game twice to look at several "endings" available (which involved a lot of save scumming), and I really liked the fact that both choose Agnes and choose yourself gave to an 'positive' ending that set both Maddie and Agnes on the path to healing. I think sometimes its easy to get worried that wanting to 'save' someone being a trigger for healing will make it easy to rely on that person too much, and to have the different endings reflect that this belief isn't actually the case was a really good choice and I really liked it. The time loop aspect was written so well too, and I sort of saw it as Maddie overthinking her every action again and again rather than an actual time loop, but even if it were read as an actual time loop it still makes sense and makes her every attempt more desperate and heartbreaking. And I know only having one choice was a requirement for this jam, but I've always liked the writing technique of using non-selectable or repeating dialogue/thought choices as a way to express a character's inner conflict. Really made good use of the jam requirements to fit this particular story, especially Maddie's pain and her slow path to healing. I particularly liked it when it came to the smoking scene, the slow difference in her choices over the four loops, how it almost seemed like she could quit before she took Seven's cigarette.
All-in-all, great story. One of those that tempts me to print out a copy so I can reread it and analyze it in detail, except this medium doesn't allow for that so I guess I'll just come back every so often to experience it all over again.