Photograph by Sylvia Plachy

For so long, I'd dreamed of becoming the Ideal New Yorker—one of those fabulously pulled-together soldiers of the street for whom every living minute moves in seamless perfection. My life would appear as if it had been ripped out of the pages of a fashion magazine; a DKNY ad with Mark Vanderloo rollerblading down Fifth Avenue, briefcase in tow. I'd get in a cab without agonizing over the driver's efficiency, or whether I'll be out of cash after I pay the fare. I'd meet a friend for dinner without first sprinting down the street to get there, barking breaths of apology into a cell phone. My fantasies of cosmopolitan cool buffered me against feelings of inadequacy, when I'd come home, thumb through spreads in Arena Homme Plus, and think to myself that eventually I'd be accomplished (or at least fabulously dressed) enough not to worry about my flaws. In the past chaotic weeks, though, none of the gloss of the brazen, pristine fabulons in Vogue or i-D could console me like flesh-and-blood people. I received a storm of calls from long-lost friends inviting me to impromptu hang sessions—all organized in ill-fitting jeans, none of which I've made on time. And honestly, I couldn't care less.

What I appreciate now are those actual New York moments when magic rises out of random situations. Moments where nothing is planned, no chic ensembles are worn, and almost no cash is on hand. They are so enchanting they bear repeating, and ideally, my perfect day would re-create those memories, emotions intact. Something like this:

It's early spring the year I arrived in New York. Some mornings, I would walk with my friend George to 169 EAST 71ST STREET, the townhouse that Audrey Hepburn would traipse out of in Breakfast at Tiffany's. Today, George sits on the stoop and scrawls away in his journal, imagining that some swan in pigtails and a Givenchy shift is cascading down the steps and flashing a quick smile on her way. I've seen many similar creatures on the street, but not here. It'd kill.

Mid-morning winds into a summer Sunday of last year, when two friends visit from California. Unfortunately, one manages to ruin the weekend with constant long-distance-boyfriend drama. We ditch her for a jaunt along Fort Greene Park, which is relaxing until heavy rain forces us to duck into trendy CHEZ OSKAR (211 DeKalb Avenue, Brooklyn, 718-852-6250). Looking like two wet cats, we manage to provide the smug buppie diners with plenty of laughs. We find the humor only after munching on pancakes and bananas with chocolate syrup. Best meal ever.

I guess in honor of my dad, the next cut is an afternoon pilgrimage to the farthest eastern reaches of the Bronx to THE SITE OF LA LUPE'S GRAVE (grave 88, row 7, St. Matthew section, St. Raymond's Cemetery, 2600 Lafayette Avenue, Bronx, 718-792-1133) to pay homage to the throaty, scratchy voice I remember from my family's living room as it wailed on the Boses. It's pretty out here—just below the green expanse of Pelham Bay Park—and I get to cancel out those variables of time and space in the midst of a quiet alignment of plots and stones, solemnly darting my eyes at corner markers until I come to hers. A photo of La Lupe stares out jubilantly from the upper left of her stone, ready to cry into song for her audience of mourners. Her presence is received with humble offerings of bouquets and fruits. I've got a single rose.

It's now late fall, and as leaves turn yellow in the hills high into FORT TRYON PARK (190th Street and Fort Washington Avenue, 795-1388), Dominican teen-agers play touch football at the foot of the Cloisters into the early evening while I munch on the salty tang of a piece of fried chicken from one of the chimichurri places below, watching the sun stroke the ripples of the Hudson through the trees.

Last selection in the set: a rainy night I shared with a friend at Chelsea's WILD LILY TEA ROOM (511-A West 22nd Street, 691-2258). Outside, a hint of fluorescence radiating from the Comme des Garçons store across the street creates white spots of light on the tar and cobblestone. I sit and watch the display, inhaling the aroma of inventive teas strained from rice and floral extracts, as Chet Baker warbles above me. Two carp play some wayward game of catch in the shallow pool at my feet, and we stay until the place closes and the Baker CDs end their run, and the warm haze of the night drifts on.