The notion that the door to hell is situated on upper Madison Avenue -- tucked behind a pillow at Schweitzer Linens, in a secret panel at the Merton Simpson Gallery of primitive arts, or even cannily hidden at Gymboree -- has never been conclusively disproved. My particular pit opened at the corner of 89th Street. There, kitty-corner from me, stood a woman to whom I'd once been engaged. We'd come to our senses in the nick of time. No hard feelings, just: no. It was proof of the city's ampleness that even though we both remained here and had common friends, we'd barely had any contact for twenty years.

Now there she was, walking down Madison. Looking good, too, in a Saks-style long green coat with a fur collar. With her were three other similarly attired women and a passel of well-turned-out kids -- Madison Avenue moms out for a stroll, a snapshot of The Good Life. Across the street, I cowered in the doorway of a Timothy's Coffees, Jets stocking cap pulled down, crazed-Vietnam-vet-style. Dirt-caked and beer-sloshed, I didn't see this as the optimum time to have my former fiancée ask, "So what have you been doing?" I mean: I could have had a whole other life with this person.

Ah, the counter-me, that ever-ripe chestnut of the middle-aged male -- one more obsessive re-deal of the existential portfolio. A moment to reflect, to consider one's life, one's times, one's place. After all, my three children are fourth-generation New Yorkers, following in the lead of my sainted grandmother who came here in 1901 after escaping murderous Cossacks by hiding in a potato sack. For a century, our family saga has played out upon these unquiet city shores, where my uncle Larry, the gambler, once won a Mott Street chinese restaurant in a crap game. Those days, it was great to be a Jacobson in the New Land. Even now, with all but a few of our robust pantheon of founding gods and goddesses -- Aunt Rosie of Lenox Road, Uncle Louie of Long Beach, Cousin Harold of Yellowstone Boulevard, Aunt Celia of Kings Highway -- lying beneath the dirt of the Elmont family plot, it was hard to imagine that our epic reign in this place would ever end.

That said, I'd just passed by my younger daughter's "middle school." The school was surrounded by scaffolding. In fact, I can't remember a New York City school any of my children has attended that wasn't surrounded by scaffolding. It appears to be a signature of Giuliani-Crew management style. Even on the brightest day, the latticework of the ever-diligent School Construction Authority sheds a Dantesque darkness: Abandon hope, all ye who enter here.

This is difficult to accommodate. After all, I am a product of this same system; both my mother and my father taught in city schools for 40 years. For us, the separation between school and home blurred, each spare piece of scratch paper bearing the bd. of ed. watermark, everyone off at three, with summers free. Public education was the family business, how I was brought up. I believe in it. Except now there is this scaffolding, this metaphorical gallows, and 35 kids in every classroom. Of course, there's private school -- those children are getting ahead. I mean, the fifteen grand aside, I'll send my kid to a private school if I have to -- I have sent my children to private schools. But I don't believe in private school. It offends my dream of New York, sullies the empire of classlessness. It makes me heartsick.

Standing on Madison Avenue waiting for the woman I almost married to turn the corner and fade out of my life for the next twenty years, I could feel the sense of place erode, and it was stunning thinking of a New York without me, a me without New York.

I had to get to the Waldorf. I'd booked myself in a week earlier. It was part of the initial walk-the-city agenda: sleep in the park one night, the Waldorf the next. The high and the low, outhouse to penthouse. Originally, the prospect of arriving at such an iconographic seat of NYC Mammon in my stinking clothes and mud-cased boots tickled me. Screw them: I had a reservation. Now I sought to fit in. I'd have to purchase a change of clothes, and it couldn't be one of those Grambling U. sweatshirts sold at the flea market outside Mount Sinai hospital. Barneys was out, too; an expense chit for "$2,000, costuming" would not fly. Banana Republic, erstwhile clothier to the colonial oppressor, now Seattle-daywear provider, would have to do. In brown cords and beige sweater, backpack in suitcase mode, I entered the muted plush of the Waldorf lobby, scanning for spies.

My mother has often mentioned the weekend she and my father spent at the Waldorf-Astoria soon after he returned from the war. Two nights in the lap of luxury: They had it coming to them, for beating the Nazis. The Waldorf was the top, famous world-round. But now $400 (!) gets you a Days Inn-style room with banging pipes, all of it crammed into space notably smaller than the room I'd occupied the night before at the Deegan, an establishment never owned by an Astor. They could at least have thrown in a waldorf ashtray to steal. But it was just unmarked glass, see-through, throwaway.

No matter; I was safe in my seventeenth-floor bunker. No chance anyone would recognize me here, I thought as the full moon rose over the office buildings on Lexington Avenue. Out there were a thousand squares of light, several filled with someone typing. Once upon a time, you could walk through the city's financial canyons at night and find solace, the great engines of commerce stilled for the moment. Now the global economy pumped ahead around the clock, without allowance for regionalized distinction between day and night. Time had become relative, a profane, endless stream.