Seems like it was premeditated! Incredible to think that he is well known. I think that the flagging and downvote is a good tool but like many things, depends on the user and its intended consequences.
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I 100% agree! When I replied with "not interested" all of his replies literally came within the span of 30 seconds. It definitely seems like he was ready in case I wasn't "flattered by it".
I totally agree about it depending on the user and situation. The flagging system has a lot of flaws... like a lot... but this was a moment where it would have been helpful - so I thought it would be interesting to point out. :)