I just read her bio! He's spent very little time up north, only a short stint in NYC which he hated, so the most likely overlap is if he ever passed through Georgia during his vagrancy. It could've been a 5 minute interaction that left an impression and now they're truly meeting in Boston. He gets into enough fights to land in a hospital eventually or depending on her neighborhood, he could move in across the street. We could do a common watering hole, too, or maybe she volunteers, I'm flexible if you want to give them an excuse to hang out regularly.