Hi there!
I have made a little Valentines Day special on my gaming channel, playing four games that somewhat fit the theme, and I gotta say... this was a lot stranger (and funnier) than I thought it was.
Much of a laugh as I got out of it, I do feel like it could give some manner of hint as to where to find each character, considering it pretty much left me up to the luck of the draw based on where I went. Granted, that does tend to be somewhat normal for dating sims, but for one where the scenarios can be so potentially short (and subversive), it'd be nice to have some indication of how to reach the things you WANT on a second playthrough. I played this twice without even realizing Grace can be dated at all, for instance - which was a bit frustrating, since I didn't consider Zane or Sheldon particularly likable from their first impressions.
But once I dug deep and got to some of the funnier sides of the game, I really started to enjoy myself, and I can easily see myself playing it again to try and see where else it can all go and how much weirder things can get, so you definitely got me hooked. And the art is pretty friggin' adorable to boot. So good job!
Your game starts at 40:17, if you are curious.