You have to go straight to talking to the guy after sorting the mail. Don't click on anyone else's dialogue. Otherwise you don't get his introductory conversation.
I had the same issue, if you talk to anyone before going to talk to the guy who fixes the walls, you won't get his little hello speech and you never get to end the day. You have to go straight to talking with him once you leave the tavern. Don't click anyone else's dialogue until you do.
