I'm pretty quiet, and reserved, but for some reason I always end up meeting people during my night walks and have had all manner of conversations, offers, and interactions. I think some people just need someone to talk to that won't judge them.
My recipe is the following: grab a drink from the nearest convenience store (ideally alcoholic), and set out into the night towards the busiest area you can find, and just watch the hustle and bustle.
Just a sample of the adventures I've had: spending a couple hours wandering the streets of Tokyo with a couple Danish tourists during their last night in the city.
Talking for a few hours in a park with an off-duty US military servicemen, after which he suggested we start running drugs from Mexico across the border -- no thank you.
However, one of the most interesting, jarring, and thought provoking interactions I had was with a young man, of obvious African descent. This took place in Bangkok. I was out on one of my night walks, and as usual stopped by a convenience store to grab a drink. I noticed the young man, sitting on the curb, if I recall correctly, having a smoke.
At the time, I was working in Bangkok as an American on a relatively cushy salary and high on life. So I walk over and strike up a conversation, expecting to hear about the adventures that led this gentleman to Thailand. So we chat for a bit, and I tell him about life in Thailand and working as an expat. I then ask him, "So what brought you out here?" He gave me a one word response, that made me realize how privileged I was. That word and his answer was, "war".
He went one to explain that his country undergoing some internal conflict, and he had fled to find a better life. Here I was, a relatively happy and well-paid American -- I really had no response other than listening to his story. We sat there a bit longer just talking about life -- two people from vastly different experiences, sitting on a convenience store curb and enjoying a chat and a drink.