Very good, loved almost everything about this. Let me get a couple of nitpicks about the art style out of the way first: I really wish the backgrounds didn't go as crazy with the dithering. I feel like it's usually best used with restraint and limited to transitions between colors; instead of a deliberate texturing choice, though, the game treats it as a way to expand the palette, which just looks too messy to my eye. The restaurant's windows in particular are some real pixel gore – I would not have complained about just forgoing the self-imposed limits and picking new colors for them if it really felt necessary.
Second, though I kind of do like the backgrounds and the sprites having different pixel sizes as a means of separating them, I'm not a fan of the UI being all over the place, especially the fact that it's not even consistent with itself (see: the text box and the other boxes). If the dithering thing saw the art maybe stick too close to the limitations inherent to its inspirations, I think this represents the opposite case where being more diligent and faithful might have paid off.
But I would call those minor gripes, especially considering the visuals fare pretty well otherwise. Alan's character design that puts detail in all the right places and the (thankfully dithering-free) sprite are nice to look at, and in a story that is already weaving several high concept gimmicks together astonishingly well, I like how much meaning there is to the pixel art style. Like all the other game-y elements, I think it's a fun way to show formally how much online gaming drama continues to haunt Saul even as he tries his best to enjoy the date.
Speaking of, it's a pretty enjoyable thematic core in general. Depicting dating culture as gamified and transactional is one of those messages that resonates every time because it's simply true, and there are a lot of additional angles to make it even more interesting. With how the time travel powers work, it's one of the VNs that manages to make the jarring discontinuity of navigating a complex web of choices feel purposeful and, paradoxically, in fact more immersive; the framing of being in control of a character who can rewind time accounts for even modes of reading like "I want to see what this funny option does". It works so well that the story doesn't have to underline the uncomfortable aspects of treating reality like a game too hard to make it satisfying when they're eventually brought up in the story.
The character drama with delightfully soap operatic twists is another thing that would have enough juice to propel the story all by itself but is expertly integrated with everything else that's going on. Though it's ultimately not the most major thread, I like everything about how the game depicts the different yet interlinked worlds of online and offline; there's a lot of good nuance in there about internet wars and the people behind them.
As a game jam submission, the VN also impresses with its management of scope. There's a lot of game design complexity involved with how complex the structure really is, but none of it ever compromises the storytelling, and the finished product looks and feels polished enough that you wouldn't guess it was made only in a month. Really, High Score Hyrax was simply a blast to read and likely uncontroversially among the jam's best.