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Ha, interesting question, really cool answers all around.
For me, it was many years ago when I went with a friend to visit a common friend that was studying in Vermont (we 3 are from Europe), and using the occasion we went to visit new York as well. One night we went to have a walk around Times Square and took the subway to get there. I was just standing there checking out the map to keep myself busy when this huge black guy wearing an even bigger fur coat that was sitting started talking to me and asking where I was going and if I needed help.
At first I awkwardly said that I didn't need any help, I was just looking at the map to keep busy. He insisted asking where I was going, to which I answered to have a stroll around times square. He got quite cheerful and said he was going in the same direction and he knew a shortcut. At that point I got a bit suspicious but the guy said changing the train we would get there faster, I confirmed that indeed the other train was going in that direction and he told us to follow him. Despite my suspicion as long as there was plenty of people around I decided to trust him and go with him.
After the change of train he told me he knew another trick about that station, everyone was going to the normal stairs but he told us if we go a bit further we can avoid those stairs. He took us to an escalator that took us into an exit straight at Times square.
In the meantime we started talking with him, he told us he was going that night to have a guy's night out with his friends and they were going to Atlantic City. He started telling us about his life, he was a music editor, and was married, and loved to help people visiting new York. By the time we got out into the street it felt like we were quite close friends and we stayed there a bit still talking, he was one of the nicest random people I have ever met, we took a photo together and he gave me his contact card in case I ever returned to NY (which I didn't).
I've thought about him ever since and wondered how he was doing. It's a great memory I have of such a simple random encounter.