Oh this will be a tough one, but who doesn't like a challenge? Winters is a serial murderer from his world, was on death row for a bit, and then was enlisted to basically fight in a war with the weapon he had in exchange for being released. He likes to fight a lot, but honestly I wouldn't mind putting him in a setting beyond his usual comfort zone to change it up.

He could be anywhere in person, so running into her in the park is something or at her shop.