Just as a heads up for anyone else checking out this game: since it's made in RPG Maker 2k3, you can press F5 and toggle "Allow uneven pixel sizes" to enable pixel stretch widescreen.
I really love the art style and gameplay concept. Unfortunately, that SSD crash you mentioned seemed to prevent as much content and polish from reaching this release, so it's a bit too clunky for much of its gameplay to be enjoyable. I did enjoy the library minigame though!
I would suggest not implementing any reflex-based minigames in the more complete release, since the engine doesn't seem to respond well to those challenges. The running physicality minigame might be better handled as just a dice roll with a nice animation alongside it.
The dialogue is very charming! As someone who is experiencing the misery of dating apps right now, I found a lot of the lines about not getting romance extremely relatable.
I'll also add that I'm very glad to see 2k3 representation in the jam. That's been my go to choice of RPG Maker for a long while, so I'm happy to see its pixel art aesthetic and "Show Picture" command strengths being shown off here.