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the 8 or so for the anime), and there is an ending (they are relatively short so not sure if I would call them a route) for each character based on whether or not Okabe Undertale let's you date a skeleton man.
When I think about it, I haven't actually played that many dating sims, besides Katawa Shoujo, which I liked, but it sounds like you weren't digging. I don't know how much of a dating sim it is beyond (I'm guessing) selecting which route you want to go down, but it is highly regarded.
I did the Emi and Haneko routes and gave up halfway into Shizune's route because communicating with her was exhausting.
Here are dating sims listed by ranking and just visual novels in general, again listed by ranking.
In a writing sense I mean, they sure blew up after that first one, and the production quality was so much higher.
I appreciate that Umineko is good(I really liked the anime adaptation of Higurashi, though I've heard Umineko's anime is pretty bad), so I'll keep it in mind but it's not what I'm looking for right quality games that I liked a lot and that are free: emily is away and love is strange.
I only have limited experience with these titles, didn't finish them, but they are highly regarded and easily available on Steam or other official channels.
And again Sakura Wars: So Long My Love and Majikoi are very good (and Majikoi's fan translation is complete).Off the top of my head I'd also recommend Majikoi, which is currently only readable through a fan translation but will be released by JAST USA sometime in the future.