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I tried some more times and ways of doing it, but I'm starting to think that maybe what's making it not work is that I don't have the orc living with me anymore. I progressed with other quests and left the Country Road quest for later... But i appreciate your help! 

Guys, I'm having a problem with the quest Country Road, the first task is to sleep until morning, at home, I do it, but it doesn't progress the quest

This game is so cute I almost died playing it. All the routes are awesome and I'm very excited to know Nasir better.