Yeah, this is a tough one! Lily doesn’t really work for sparring since she fought with magic in canon and even then, she wasn’t good with fighting magic. It was more brewing, chanting, drawing magic circles and focusing powers to cast demons out. When she was a teenager, she ended up in jail for a few weeks. The people in her hometown tried to blame three snakebite deaths on her after they tied her up and set poisonous snakes on her but at worst, that was her magic being out of control rather than her actually trying to kill anyone. Her grandmother managed to get the charges dropped with magic but Lily was forced to leave town after that. But it’s not exactly something she would admit easily, especially in Death City!

It wouldn’t be too hard for them to run into each other somewhere but the bigger question is where it should go from there. I could kind of see her mistaking Winters for a demon or something of the sort from his appearance.