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Steins; Gate might be cool, I loved the anime adaptation of that too.
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.
Some guidelines for what I'm looking for: When you say "dating sim" do you mean something like Tokimeki Memorial or Love Plus where you build up stats in order to date a girl or are you looking for a visual novel where you can date different girls?
I haven't played too many of the former definition but the Sakura Wars games are a great mix of dating sim and strategy RPG, I'd highly recommend So Long My Love on the PS2 or Wii.
The only one I've played is Katawa Shoujo, it's free. The guy you play as kinda sucks but I could connect with it a bit 'cause the game is all about these ppl with disabilities.
If you really like it, the game has plenty of replayability quality games that I liked a lot and that are free: emily is away and love is strange.