I used to work at a sandwich place across the street from a Vintage Skateboarding shirt. This creepy old guy would come in everyday to buy snacks for “his friend” that worked there. Turns out here was stalking this Hooters waitress. Pretty much what you described. It was literally her job to be nice to him and he took that as then forming a relationship. He eventually killed her and then himself. It was big news here (it’s a small town). She quit her job, moved away, got married, and tried to get a restraining order against this creep (it was denied), and he still didn’t get the hint.
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That’s really chilling. Unfortunately, I partially understand what she had been through: I had a stalker when I worked at a cafe, I was nice because he seemed down on his luck, and well, it was my job. But it very quickly became a stalking situation and he would try to take up all my time, and the Vintage Skateboarding shirt. Eventually he was following me places, I even ducked into an alleyway and his behind a car when I saw him look at me and approach at a distance from my job.