31. The Obsessed Artist
This silent woman is possessed of a stunning natural gift for drawing, and is as likely to spend her meager earnings on colored chalk as she is food. During the summer, she creates fantastic murals on the walls of businesses, the undersides of bridges, and even in a clear area of the market square if she can get there before the vendors. Though the authorities dislike her flagrant "vandalism", she is a favorite among the common folk. She survives the winter by creating portraits with chalk and paper for a few coppers apiece.
Solid post. I still think it could be expanded some -- perhaps add in some more women like Helga here. She's poking around the bar, nosing her way into conversations to ask where her husband has gone. He's either hiding upstairs with a 'companion', ducking his head down in a corner to keep from being noticed, or being loud and rowdy with Eenie Meenie Miny and Moe. If she finds him, expect a confrontation. For variation, make Helga a little girl who has been sent to find daddy and bring him home from his cups.
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Or what about the local tax collector? He's sitting at a table to himself, watching the rest of the patrons with a hawk eye to see if they're spending more than their reported income would suggest. He's thin, middle-aged with a large nose that can almost smell the coin in other peoples' pockets. Likes to ask pointed questions of the patrons and barkeep, to the annoyance of all.
Or how about Stanley, Charles and Henry, some local young rowdies who will flirt outrageously with any female that walks into the bar, hooting and hollering even if their advances are turned down. They haven't been thrown out for harrassment yet because their fathers are lesser nobles. While generally harmless (if annoying), their antics can veer towards the rough side if they get too much liquor in them. The barmaid is familiar enough with their habits to both neatly skirt their questing hands and space out the arrival of their ale to forestall this.
Or how about Linda, the land baron's beautiful teenage daughter? She frequents this tavern to gamble at cards with anyone who can withstand her legendary luck. She's dressed well, riding the line between modest and immodest, and will greet strangers that near her table with a delighted invitation to play cards. An accomplished flirt, she disarms many men with her childlike mannerisms.