(Not book-related, and more dating sim with actual game elements than visual novel, but the trailer made me laugh so I thought I'd share. Looks like it's available for Windows and Mac at the moment.)
I started playing the free version over the weekend out of morbid curiosity, and it turned out to be way more entertaining than I expected. Everyone's horrible in their own unique way, but none of them are horrible in a puppy kicking kind of way.
There's Nate (uptight and expects everyone to be as good at everything as he is), Shiloh (enormous suck up), Everett (abrasive and can't think for himself), Bae (snarky and annoying), Pran (refuses to hold a conversation), and Jeremy (so very emo). And then there's the heroine, who doesn't care how annoying, frustrating, or difficult to like any of the guys are, because they're hot and there's maybe a chance she can date one of them. She flat out tells them this too - one of the things I'm loving about the game is that nearly all of the characters are completely aware of the things about themselves that put others off and don't try to hide those aspects. There are also a few fun non-dateable side characters. My favorites are Lynn, the school nurse who tries to force everybody to get along, and the little con artist/luck manipulator in the shopping district.
I've put about 5 hours in so far and still haven't finished my first playthrough. Future playthroughs might not be quite as much fun due to scene repetitions, but thankfully there's the usual "skip" button and one unusual feature the developer kindly included, an in-game spot where you can enter cheat codes. During my second playthrough, I plan on using the one that'll let me avoid having to constantly check and maintain my reputation with all the cliques, because one full playthrough of having to do that is enough.