As far as I can tell, You need to talk to everyone when in both instances in the town.
The dream you can't avoid talking to both venders there. You have to have the purposes of moving forward.
After escaping the sewers, you have a few conversations to gain the trophy. It appears to be glitched too, so I'll tell you how I got around that.
Far left hand side. Kid cleaning the floor with a mop. After conversation, try talking to him again.
The noodle vendor the opposite side of the path to him.
Then the trophy gets a bit weird here, after this step, I'e heard of people unlocking the trophy and others not.
3rd person is the kid eating fish in the noddle bar, eavesdrop on the conversation.
4th person is the guy on the bottom right of the map that offers you tell the "Noodle lady" of your situation.
If it doesn't unlock still.
Return to the 2nd person you talked to and go through the dialogue.
If it still doesn't pop:
Go back to the kid cleaning the floor and annoy him a couple of times.