How to Be An Undercover Hooker


Disclaimer: I have never been an undercover hooker (or a real one). But back in 2005, I begged my way into the New York Police Department’s training class for Operation Losing Proposition. Part role playing, part rote learning, the class taught fresh-faced cops how to fake the world’s oldest profession (hint: come on too strong, and it’s entrapment).

After a few short hours, I’d passed a multiple choice test and earned the right to tell my proud parents: If I were a cop, I could be a hooker.

Armed with a 46-page handbook (complete with glossary) from the class, I’m now prepared to share the best – and worst – tricks of undercover hooking so you, too, can get a leg up on New York’s finest.

Jessica Bruder


I’m a curious-minded storytelling junkie, an Oregonian reporter, and the author of Burning Book: A Visual History of Burning Man. I’ve also written for The New York Times, The Washington Post, and The New York Observer. When I’m not writing, I enjoy tossing myself downhill on a snowboard, playing electric guitar, learning how to make things from steel, wood, and propane, wearing goggles, and nestling plants into antique coffee cans.