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As I came around the corner of Chase, walking north on Maryland, an older man carrying some shopping bags crossed my path. He stopped immediately upon seeing me, saying “You live around here?” “Um, no I don’t”. I tried to keep walking, but then I heard “Huh, you look familiar. I live real close, I think I’ve seen you”. I tried to be polite, since most street harassment I experience doesn’t start with such get-to-know-ya tactics. “I guess I eat at City Cafe sometimes”, “Oh, maybe that’s it. I’m about to go home and watch a tennis match, you like tennis? Want to come over?”
This is where I finally realized that this was not just a neighborly interaction, it was a little predatory. Still not wanting to be rude (that’s female socialization for you) I said “No thanks” and turned to walk away. He continued his original path of walking the opposite way, but I heard a “You look pretty today” WAY after our interaction stopped. He said it while far enough that he didn’t have to risk me responding negatively, but it was so obvious to me that he ALSO said it loud enough that I would hear him.

It wasn’t until I got to where I took this picture that I thought, “Wait, was I just harassed?” What is the point of stuff like this? Getting the last word? Letting me know that he’s entitled to judge my appearance whether I’m interested in him or not? Does he think he’s being nice?
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Here is my take on it, from a guy’s point of view. The point of it, IMO, is the aggressor is trying to exercise control over you, mental control. He was hitting on you, got you to engage in conversation, then you clearly indicated you wanted nothing further to do with him. He probably said the last comment very loudly in a fleeting effort to continue the conversation, to regain control. You made the right choice in leaving once you realized it was becoming a creepy encounter.