Thanks! The issue I have is nothing indicates to go back through there and talk to him. I would have never done that naturally if there wasn't an achievement for all of Ross's skills (I'm on xbox). After beating the boss of the dungeon I usually 'warp' out since there's nothing else to do. You would only ever get this if you backtrack through the dungeon after beating him, and even then he's just sitting in a corner with no indication to talk until you walk up to him, or do like I did and go back through it looking for stuff you missed. I think the subquest giver did mention that she thought he was lonely and might need someone to talk to when I went back and talked with everyone though which is why I went back through there.
Anyways, big shout out to this community for being so helpful and friendly to us xbox folks!
Red Reaper achievement
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