Address: 500 E. 9th St.
Mayors Bloomberg and Giuliani did a great job of making the homeless seem invisible. Any reports you read about New York prior to their administrations tell tales of sleeping bags and cardboard spread across on sidewalks up and down the island. These days, you'll pass a down-and-out man pushing a shopping cart through Central Park or a couple wrapped in a filthy blanket in your building's lobby, but generally the homeless are kept out of the public eye. Tompkins Square Park is one public area in Manhattan where you less fortunate still congregate. Yes, you can see the remnants of Occupy Wall Street and dog-loving gutter punks pretending to be homeless in Union Square, but if you want to spend Valentine's Day with the genuine article, head over to Tompkins Square. Just be sure to put a brown bag around your bottle of Mad Dog or you might get rousted.