After the initial conversation (running through all options), re-initiate conversation.
I saw an option then, which was "You seem to come around here a lot" or something like that.
Then these happen:


I have 125 Speech/CHA 10, Good Natured, MagPers... don't know if that helped.
I wonder if age is read in as a variable. Monocle is a bit old.
Was wearing leather jacket.
Had all the Outdoors Perks, stepped on almost every grid square on WM- there might have been a few corner peices bt the ocean that are really tiny that I missed, also entered every named area except Glow and Raiders.
Been to all rail stations.