It's so insane how different tone-wise pages 37-54 ( and 42, 43, 44, and 50 especially ) are to the rest of the comic that I think it functions as some real unintentional storytelling about the author. Shadman never really grew out of his shock, edgy, "anti-cringe >:(" phase that made him who he was in the mid 2010's and you can see that plenty throughout the first 36 pages. The constant mockery of Jaiden's eccentricities, her mannerisms, the way she speaks; making her act like a baby with her mom; calling an "autist" over and over again.
Then, all of a sudden, it's none of that at all. It's an ambient, moon-lit night. It's a POV from Shadman (or at least his self-insert) having a date with Jaiden. She still talks like he usually makes her talk but there isn't really that contempt that was there before. For the next 16 pages, Shadman seems to have some real moments with his simulacra of Jaiden's online persona. We see him watch her act without a care for how "immature" it may look, completely sincere about everything she's feeling at that moment. Here with her, he can put his guard down. Here with here, he doesn't need to be the "Shadman". Here with her, he can be who he is.
There's a sense of yearning that comes from these pages. A sort of envy of someone like Jaiden, untethered to need of having to come off as "serious" all the time. This is the common thread of the entire comic. The reason why Shadman decided to characterize Jaiden the way he did, initially, was because this envy persisted in a way he did not want to admit. As a result, that envy manifested itself as contempt as a way of belittling her to him feel better about himself. At some point, however, he came to the realization, consciously or not, that he wants to, in some way, be more sincere, let go of larping as his permanently disagreeable persona. This is how you get his fictophile fantasy at the end.
This is all very armchair psychologist i know but I can't help but read it in this way.
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I puked a little on page 31