What if Jack has a cafe/bar that he goes to after every couple of deaths, he buys something small like a coffee or a beer and always leaves without paying, there has been a Do Not Serve picture of him on the wall since the bar opened (in the late 1800s) and the picture is running joke among the new employees, “oh he’s our bar ghost, he comes in gets a beer flirts with whoever is bartending and then leaves without paying” “I heard he’s been here since the bar opened in 1889!” And the employees all laugh and trade stories until, inevitably, he waltzes in, all the employees stare at him. He flirts, has a drink, he leaves. Total chaos.