Free Don't Get Too Comfortable by David Rakoff

because they can.

J.D.V., M.I.A.
    T hey say New York is a Twenty-Four-Hour Town. I suppose that's true, if by Twenty-Four-Hour Town they mean you can probably get a plate of eggs somewhere or wander bleeding into an emergency room for suturing. But in the wee, small hours, it can be a very quiet affair. It is not the round-the-clock party it purports to be. That's why stories about staying up late in New York so often seem imbued with a gin-soaked wistfulness, even this one about an exuberant late-night scavenger hunt through the streets of lower Manhattan. Or maybe it's just the memory of it that makes me want to reach for the bottle.
    This escapade is called Midnight Madness, named after an apparently crummy 1980 movie about a scavenger hunt starring David Naughton of Dr Pepper commercial fame. A sporadically annual affair, it is the brainchild of Mat Laibowitz, a monomaniacally brilliant young electrical engineer who has seen the film dozens if not hundreds of times.
    I am part of the White Team, an apt color for us, since in comparison to our thirty-odd, twenty something opponents, we are snowy-locked geriatrics. Jaime, our team captain, reads the preliminary instructions for how the hunt will work: “Each clue will lead you to the location where the next clue is hidden, and so on. When you find one, call into HQ immediately. This starts a one-hour timer. If you haven't found the next clue after one hour, you can call again for a hint.
One hour!?!?
Oh my god . . .” His voice trails off with a what-have-we-gotten-ourselves-into weariness. Or perhaps I am projecting. Anything that calls itself Midnight Madness by definition means we won't be going home anytime soon. It is scarcely eight o'clock in the evening. It has been a good while since 12:00 a.m. held much attraction for me beyond being a perfectly lovely time to be ensconced in the comfort of my own home, sitting in my underpants, contentedly worrying about something.
    Our playing field is the eastern half of downtown Manhattan, a vast area comprising Battery Park, Wall Street, Chinatown, the Lower East Side, the Bowery, Little Italy, and NoLiTa, a term used to describe the neighborhood to the north of Little Italy, a few city blocks positively metastatic with handbag stores. It will be an evening of more than seven hours' duration and two hard-won insights, the first of which is that I am not a facile puzzler. Scratch that: it goes deeper than that. I both suck and blow at puzzles, riddles, and games of all sorts. I am a reasonably intelligent guy, but when called upon to bring to bear strategic thinking, a competitive nature, and smarts all at the same time, I don't show myself to be just an idiot but the very worst kind: the voluble dolt who has no idea how stupid he is. Case in point, the first clue that kicks off the game:

    Clearly this means that we are to hie ourselves immediately to Manhattan's nearest outdoor Frida Kahlo painting. Even though I have never seen anything in the city that might remotely fit this description, and a Frida Kahlo painting would more fittingly have “One Eyebrow” as its clue, I say it like only a moron wouldn't know this, as though the slip of paper actually had “Go to the Frida Kahlo painting!” written on it. My voice is almost exasperated at how much time we're wasting just standing there
discussing
. One of our team members—thankfully a mathematician who does this sort of thing for a living—steps in and points out that the shape of the clue, the way it is written, might indicate something. Could it be referring to a street corner? Also, the shared “E” probably suggests that rather than looking to the meaning of the words themselves, perhaps we should look to the letters. An anagram, maybe, of Bowery and Hester? It takes him as long to solve it as it took you to read the preceding four sentences. But he is kind in addition to being clever. “Or we could,” he says, looking at me politely, “go looking for a