I used to intern at an organization on the dividing line between the nice and the rough edges of town. I was walking from our parking lot to the building and this guy walks up and starts chatting with me, asking me somewhat personal small talk questions — do I like my job, where did I come from, what do I want to do next, etc. I gave him curt answers and tried not to reveal too much information, but he keeps walking with me for a couple of blocks and I’m starting to get super creeped out, especially when he follows me to the front door. But then he got out his access card and it all clicks into place — he’s actually someone who works at the company that I’d briefly met and didn’t recognize. I apologized, we laughed, and ended up becoming good friends that I still keep in touch with.

All this to say — if you treat a legitimately well-intentioned guy like a creep, he will understand, because he is a legitimately well-intentioned guy.