I see that Umineko has already been recommended, but I do want to mention it again. Higurashi (the first work by the author, a few characters are in both, though none are major) is also good, though it has more anime bullshit. No dating, but some shitty jokes. That's a lot more horror focused than Umineko. Ciconia is also good, though that isn't finished yet.

House in Fata Morgana is supposed to be fantastic, and I haven't heard a single bad thing about it, though I haven't read it yet. I've heard so many recommendations and have literally never heard any criticism that isn't 'it handles it well, but there's some heavy stuff," so I feel safe reccing it without having played it.

The Zero Escape games are good, and the Ace Attorney games are as well. The Ace Attorney games on steam are the best in the series, and you can play either without any prior knowledge.

I'll list some that I haven't played that I'm less confident in here. 428 Shibuya Scramble. Coffee Talk. Heaven Will Be Mine. Raging Loop. Spirit Hunter. We Know the Devil. I own all of them, but haven't gotten around to playing them yet.