Some guy on the street asked me if I knew where the nearby salad restaurant was. There was only 2 ways this could go. Either he wanted a salad for lunch. Or, as you suggest, he was testing me. Was I apart of this fabled salad group or one of the forsaken "others"? The pressure was on to say the least. I don't normally believe in a higher power, but I said a quick prayer for help to get me through this challenge. I gathered all my strength and told him "just a block that way" as I pointed down the street. Now, I could only wait for what felt like a millenia. Finally, he let slip the words "cool. Thanks" as he headed in that direction. I think i passed his nefarious test. But the only thing I'm sure of is that I barely made it out of there in one piece.
Edit: originally, the comment I replied to said that no question was innocent
This situation sounds like what restraining orders are designed to help with. IANAL, but restraining orders generally cover all types of communication, including social media. Showing that he has continued to harass you even after blocking him is good reason.
Out if curiosity, have you ever tried calling his bluff? Reply with how would he improve it by saying any constructive criticism is appreciated. Something like
Depending on how you're feeling, you could incorporate tagging their company. Use the same language they used. Something like
That said, it seems like the time to reply like that has past and it's best to ignore/block him at this point.