Confessions of an Upper West Side Private Eye (Whom You May or May Not Know)

By Anonymous

I’m a private investigator. Before you picture a trench coat, fedora, and a half-empty flask of whiskey, let me quash that cliché — I wear jeans and t-shirts, and I might be standing politely behind you at Zabar’s while you buy nova.

I live on the Upper West Side. I have a graduate degree, and a mortgage on a co-op. To protect my career and my clients, I’m keeping my identity to myself.

Friends are fascinated by my detective work and press me for stories at parties. They want to hear glamorous tales about rooftops in Rome, car chases, and switchblades at the ready at midnight. My reality is far humbler and often more amusing. Most days, it’s about using the phone, searching the Internet, and watching perfectly ordinary people do perfectly ordinary things.

My first assignment, eight years ago, was a trial by anticlimax. I spent twelve hours in a parked car waiting to see if a man would leave a building. That was it. Actually, the man did leave. He went to the gym, had lunch with a friend, and bought things at Duane Reade. Thrilling, right? Because I had a lot of time, curiosity, and a smartphone, I figured out who he was and what the case likely was about. The truth turned out to be juicier than a Duane Reade run.

Field work requires methods that you don’t see in movies: protein bars for sustenance, creative bathroom-break strategies, and a high tolerance for sitting still staring at a door — I once sat so still for so long outside a construction site that a large rat came out and ran right across my toes. Audiobooks and language-learning apps are essential for battling boredom.

Best practice is to have two investigators on stakeout, so while one handles bodily functions the other can keep “eyes on” (that’s the lingo). Clients, however, don’t always want to pay two agents. So after a few solo stakeouts, I learned some tricks: rent a car with tinted windows, bring a blanket for extra discretion, and master the ability to multitask.

I’ve tailed a marathoner-in-training in Central Park (during their workout), posed as a potential nail-salon customer to get inside a building, and pinpointed someone’s whereabouts by tediously advancing one screen at a time through Google Streetview for 6 hours.

My work has recovered a small fortune in nanny-swiped jewelry before a pawn shop could resell it, discovered an unauthorized press-leaker in a city department, and unfolded one scandalous cheating-spouse situation that a soap opera writer wouldn’t be able to sell because it would have sounded too improbable. Once, I posed as an apartment hunter to extract secrets from a real estate agent.

Why did I become a private investigator? I had a successful first career and wanted new adventures and challenges beyond a desk. Childhood fascinations with Encyclopedia Brown and Sherlock Holmes never entirely left me. I love a good puzzle. There’s also moral motivation: I only accept case assignments in which I think I’m on the side of the “good guys.” Call it corny, but my ultimate client is the truth. And sometimes the truth needs a hand up. That conviction keeps me honest and makes my cases more compelling to me; if I’m chasing what’s real and helping someone right a wrong, I have extra energy and resourcefulness for getting to the goal.

My path to P.I. work was an anomaly. In 2017, I met a senior P.I. working on a close friend’s divorce case. I seized the opportunity to ask him: how do I get to be a private detective? The bald, unsmiling ex-cop (who actually did fit the cliché pretty well) said P.I.’s, who are mostly retired cops, learn on the job, by being assigned alongside more experienced investigators. He admitted my unique, non-law enforcement background could be useful to his agency, and later agreed to take me on as an apprentice. (He sardonically but affectionately nicknamed me “006” — “Because you ain’t quite 007” he enjoys reminding me.) Investigators must be licensed by the state, but to keep my name out of the publicly viewable NY Dept of State database of licenses, I work under my employers’ agency licenses. Clients hire the agency, and the agency assigns and pays me by the case. But compensation almost feels like a bonus on top of just getting to be a real-life private detective.

People ask if I ever worry about danger. The answer is yes — but the danger is rarely physical. It’s awkward conversations, staying within legal boundaries, and the risk of being “made” (more lingo). It’s also the ethical weight of what I uncover. You see into people’s lives and you carry their secrets for a while. That can be heavy. It can also be reassuring: a missing friend found, a fraud brought to justice, somebody’s peace of mind restored.

Why share any of this? Because Upper West Siders assume they don’t personally know any detectives — that they exist only in movies or live in other boroughs. The truth is more interesting. We’re your neighbors. We could be the person who waves hello at the mailbox and notices things.

Next time you’re on Broadway buying bagels, remember: that ordinary person behind you might be watching for a living. Not because they’re suspicious of you specifically, but because they’re curious about life’s mysteries — and can’t resist solving one.

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