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I struggled with that one at first too!
Here are the steps to unlocking it:


-Start human/witch route
-Pick either: Just hiking / Came to meet you / Studying magic (doesn't matter)
-Ask about his pack
-Pick either: Keep going / Stop somewhere closer (doesn't matter)
-Ask him to stay
-Offer him any food
-Pick either: It's lovely / It's too cold!! (doesn't matter)


And there you go!! 
Hope this helps :-)
Have a nice day  (*¯︶¯*)

hey, you can find a «timeline» button in the settings that shows you the dialogue choices you haven't made yet + what dialogues you should choose to find a certain ending :]