There are moments in life, in some lives, in my life, when one becomes unmoored. Something or someone cuts the bond between anchor and ship, and the sailor is cast adrift. Perhaps a violent squall snaps the tether; perhaps a villain slashes it in the night; perhaps you sever it yourself in a drunken flourish of enthusiasm or at a tranquil moment of lucidity; perhaps you simply wake up one morning and find that you've drifted out to sea.

I sailed into New York harbor in January of 2000, bright with the hope of a new century and intent on ending my itinerate ways. I loved the city instantly and passionately. I marveled at the buildings and the bars and the buses and the bagels. It seemed as if a hidden choir roared Ode to Joy while I grinned my way down the tumultuous avenues. I would often stop suddenly to absorb some new experience--the morning sun reflecting from shining skyscrapers, crowds swarming through a rumbling subway station, a saxophone singing softly in the park at dusk. Elation would flood through me, and I'd imagine throwing my hat in the air like Mary Tyler Moore. My New York moments.

I found a tiny burrow of my own in the beautifully gritty East Village. I'd loll on the fire escape at the foot of an urban forest with a beer in one hand and a glowing red-tipped cigarette in the other as Tom Waits sighed from my stereo. I discovered a buzzing, eclectic cafe around the corner where I'd sip tea for hours as I worked or wrote. Sometimes, I'd strap on rollerblades and fly along the rusting, industrial East River; dodge the Chinese immigrants who fished in the proud shadow of Old Man Brooklyn Bridge; roll cautiously over fish oil leaking from the stinky old Fulton Fish Market; shimmy past ogling tourists under the passive gaze of the Liberty Statue as I pivoted around the tip of Manhattan; glide along the pretty brick plaza beside the Hudson River slipping nimbly between afternoon strollers and upset yapping dogs; then cut through the Greenwich Village and dodge the traffic crawling past elegant brownstones.

Brimming with optimistic fervor, I started a software company for fashion e-commerce. I met pompous investors, beautiful models, ambitious entrepreneurs, and old Jewish men from the "shmata" (Yiddish: rag) trade. I excitedly shared my progress with friends and family and looked forward to what would come next. But then, the market collapsed, and the investors' internet enthusiasm washed away, taking my poor hopeful startup along with it. I awoke one morning to a call from an ex-girlfriend. Some planes had crashed into the World Trade Centers. From my roof, I saw them writhe and burn and fall fainting to the ground.

I struggled to find work for a time and fretted as rent costs threatened to force me from my new haven, but New York and I persevered together. I found a job; the city began to rebuild. I turned 30 in a cabin in the Catskills with fifteen friends toasting my age. My early thirties were happy. I was still young but confident now with friends and girlfriends and money and hope. A friend of mine found a sunny, smiling apartment with low rent and a roof deck overlooking the tumble of the East Village. We moved in together, and our parties were "fabulous." It's true that I began to take the city for granted, and my New York moments came less frequently, but they were replaced by a deeper love. My first experience of New York was a lusty embrace; later, the city and I held hands sweetly.

At 35, something changed. My friends married themselves off in a sudden rush; there were four weddings one happy, poignant June. At 36, most of them had new babies. Some moved deep into the outer boroughs, and I would see them less often. Others left the area entirely. My roommate moved to Chicago where she could afford to buy an apartment and settle down. I found a new roommate. He was pleasant and interesting but wasn't really my friend and left nine months later owing me money. I found another roommate and then another. They were friends but didn't stay. I had a couple of romantic relationships, weighed down by uncertainty and indecision. I didn't stay.

I have become tired working in technology. I enjoy the freedom and flexibility of my freelance job, but I work too hard and don't earn enough. The thrill of creation has subsided, and the dream of entrepreneurship has lost its glow. I started blogging, not with any grand plan in mind, but because I felt as if I had lost my voice. For the past year, writing has been for me like a hot fire in a cold dark room. It keeps me warm.

I'm 37 now. My last roommate just moved out. I cast about half-heartedly for a new roommate, but in this economy, there are no applicants. I decided it was time to live on my own, and I've been prowling for apartments. What I have seen has been cramped, dark, and expensive. Some places might suffice, but I can't commit. Perhaps it's time to follow my brother to Philadelphia, where costs are lower, and I have family and a friend or two. Philly will never ignite my passions as New York has, but it is old and pretty and proud. Yet, I worry that my brother will not stay, and it will be more difficult to meet with my clients or find new work. I have a new lover in New York. I like her, the relationship holds promise, but it progresses slowly. Philadelphia is not so far, but perhaps it's too far for a fragile new relationship.

I went rollerblading again yesterday. The sky was gray and the air chilly. The path along the East River is closed and has been for five years. The work was supposed to have been completed two years ago. The alternative path, along the highway, is rutted and crumbling. Fulton Fish Market has moved to the Bronx. The industries along the river are being replaced by condos. But the Chinese immigrants still fish, the tourists still ogle, and the Liberty Statue stands serene as ever.

My ship has been quietly slipping from the harbor these past two years. I can't stay out here in the open sea. Shall I tack back to port or sail on? Even the idea of leaving makes me miss the city, but I cannot even remember my last New York moment.