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What are your favorite "gotta go in blind" games?
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Dwarf Fortress, probably.
That one's tough. I went in blind when the steam version released and had a blast. The actual "game" part is not challenging once you figure out the basics. The fun of it is the stories that spring up that are mostly out of your control.
So, I'd say going in blind, but being open to asking questions or googling specific things is a great way to play it.
I think the Steam release definitely makes it easier, especially with the tutorial. I tried to get into the original version about 10 years back and let's just say going in blind was a very different experience.