I hear ya.
Back in the 70's, my dear friend and I (at the ripe ole age of about 18) lied to our mothers about where we were going and went to NY for a couple of days. We stayed at this run-down old hotel in Times Square (complete with a bell-boy we immediately christened "Igor"),made the rounds of bars and coffee houses, met the most interesting people including a guy who offered to show us around - he was completely harmless.
We learned a lot, had a great time and never felt threatened. We had our guide, after all. :-)
It was a wild and crazy time in NYC. The only time I lost my courage was when a college friend (a nice young lady) insisted we go to a show in Times Square that was in some cellar someplace that featured a fire eater and assorted freaks of nature. I hightailed it out of there, heading for the wilds of New Jersey. As someone once said, there are minerals as well as bacteria in soil.