Walking up Park Avenue this sunny afternoon, I noticed a homeless man with a standard cardboard sign. A business card, a billboard, a resume. For many homeless in New York City, these signs are their voices, their pleas, and even their stories (truth be questionable). And unlike so many other similarly scribbled placards, black marker on dirty brown cardboard –this particular one actually penetrated my stubborn, all too often closed-minded, pre-determined, sweeping generalizations. His sign pleaded, “I’m all alone. I have NO ONE.”

Something about his loneliness spoke to me. Like he was looking to relate to someone – and figured everyone can relate to being lonely (not necessarily everyone could related to being hungry or homeless). He was using loneliness as an “empathy driver” that would potentially have someone feel bad and contribute some money to his money-collecting vessel. (I didn’t.)

But I am too much of a jaded New Yorker. I trust no one and doubt everyone. So I started thinking of this homelessness of a kind of business. It’s like Homeless Marketing 101. Get inside your target market’s head and appeal to them. The bums with the signs “Need money for beer” could be panhandling on the Lower East Side, where they attract young hipsters to give them a laugh and a buck.

There’s the crippled man on the 6 train with the festering, exposed gangrenous leg. He wheels himself between the trains day after day showcasing his diseased limb for all to see. My boyfriend said, “Well he wouldn’t get anything without the leg.” I guess that’s true. His marketing is appealing to our sympathy for his physical pain.

This particular lonely soul chose to market on Park Avenue and 32nd Street – hoping to connect on a different kind of a pain – loneliness. So I wonder, how many of us did he touch?