> Where? In New York, Chicago, and San Francisco, the only people who do that are begging, preaching, or rambling incoherently.
Agree with the other replies to you; I've had lovely chats with people on the subway in literally all three of the cities when I've visited. Also at the laundromat, or at a bar, at a museum, and other places.
> ...did any of those people exchange contact information or form any lasting connection?
I never made a lifelong friend from these conversations (though I have received business cards or other contact info), but I got a sense that I mattered to a stranger, even if only for a little bit. That's certainly part of what the article is talking about.
> The mood afterword is "can you believe that creep?" not "wow aren't we so connected!"
I can genuinely tell you that many conversations I've had did not end with either side thinking the other was creepy.
Of course, I've avoided conversations with people who I felt were creepy. Typically, these conversations happen when the person is speaking to me and I've given pretty clear body and vocal language that I am not interested in speaking.
I do my best to initiate chatting only with people who show interest in talking. Having an idea of who's interested in that takes practice, and some other identification skill I have a hard time describing, but which would likely fit the definition of "emotional intelligence."
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Here's a little chestnut similar to what btmorex mentioned:
A young couple moved to a new town, and upon driving up to their new home for the first time, saw their neighbors outside. After a few pleasantries, the young couple asked, "So, we're wondering, what are the people like around here? Is it a good place to live?"
The neighbor paused, then said, "What were your neighbors like at your last town?"
The young couple agreed, "they were great!"
The neighbor, audibly relieved, said, "well they'll be great here, too."
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What you look for and expect from others will greatly color your experiences. I figure most people are generally friendly, and I tend to be able to recognize when someone wants to chat... and they likely see my desire for a friendly chat, too.