I am always afraid I am about to become one of those bitter New Yorkers. Someone with a constantly sour expression on his face and wrinkled, yellowy skin like an old front page. That person you see in the deli who screams: “Eight dollars for grapes? This city is for yuppies!”

Not long ago, in 2009, I went on a trip that sort of put me on the fast track to becoming a bitter New Yorker and I need to tell you about it before you find me raving on the street corner and nervously pass me by.

This story needs to be told without much fictionalization or allegory, from my point of view. It’s not like I want to do it this way. I wish I could transmute my middle-aged gay pain into some teen vampire drama. But I do need to bend the truth a bit or I will get into even more trouble. So think of this as a memoir with a fictional $3,000 sheer Thai silk veil lightly draped over it.

Let me just launch into things: I am a freelance writer, and I have been living in the city for over fifteen years. Around 2007, I started writing the Retail Reviewer – a popular column which appeared in the Thursday Styles Section of a major newspaper which, for legal reasons, I will call The New York Paper. I was a freelancer for them. I didn’t get any health insurance or pension plan or expense account or office space. I wasn’t even invited to the Christmas party.

In October of ’09, I was invited on a trip organized by a shopping website for men that I am going to call Dudester. Dudester invited 150 writers, editors and bloggers to get on a plane and go to an undisclosed location. A “Mystery” tour. It was co-sponsored by an airline I will call TripBlue and would promote a new TripBlue destination as well as fifteen other brands that had attached itself to the trip like fungus. We were all to meet at the TripBlue terminal. At the gate, we would find out where we were going. And when we did, we writers, editors and bloggers would all clap enthusiastically, trying to exude excitement that this whole campaign meant something to us.

Let me explain. If you haven’t been to Manhattan in the last ten years, you should know that it no longer trades in durable, fungible goods except for artisanal cheese and celebrity cupcakes. These days, the city is a marketplace of intangible ideas and the internet efforts that promulgate them. Now people make millions by crowd-sourcing, aggregating and hedging funds.

Dudester is one of the city’s new internet success stories. It’s a website that aggregates information and gives tips and updates on shoes, gadgets, and clothes for men in the much sought-after 26-35 age demographic. The start-up started with three people in a downtown office. It now employs eighty and is bleeding precious ad dollars from print journalism, speeding up the collapse of traditional newspapers like The Paper.

Dudester was founded by two straight guys in their late twenties named Peter and Dan who are friendly and hot in a frat-boyish way. They have good bodies and cool spiky haircuts and are making money as easy as a sneeze. Peter and Dan of Dudester are studs of the city’s internet culture. Every brand wants to get in their pants so they can appear on their shopping website and get sought-after attention from their consumer guy-niche. In their inevitable profile in The Paper’s Business section (“Dude, Where’s My Internet Phenomenon?”), they have this look of incredulous, doofy wowness on their faces, similar to the way Matt Damon and Ben Affleck looked when they won their Oscars at the ages of twenty eight: “This award is for me? Wow, I can’t believe how easy it is to be successful! The world is so cool!”

I wish I had their naturally lubricated ability to make money but I’m the opposite. Instead of creating a lucrative web venture I decided to write poetry and feel suspicious about capitalism and my place in it. I moved to the city and became a performance artist/comedian/poet/writer. Ka-ching!

I spent my youthful leveraging energy in downtown gay bars, getting in good with the drag queens and club promoters so I didn’t have to pay a cover for Sperm night at The Cock. Instead of working my way up the socialite ladder, I achieved minor downtown clout in the alterna-queer scene.

I was a drug addict butterfly in my friend’s experimental opera, I sat naked on a fake rock in a gallery for a friend’s friend’s art opening, I portrayed Joseph in a live nativity scene, gazing over the rippled abs of a nude gogo boy Jesus, and, perhaps one of my proudest achievements, I helped create a naked, glitter-smeared amateur dance troupe. (There are about twelve of us, we dance in skimpy outfits and then get naked. We usually get paid in drink tickets. To be fictitiously consistent, I will call it The Sparkle Squad.)

I also perform wherever I can: comedy nights or variety shows or storytelling gigs in bars or art galleries or clubs or cabaret spaces, sometimes in actual theaters. I’ll get a free drink or—if I am lucky—a bit of money. The side room in my apartment is full of wigs and costumes, as well as a plastic gun, a purple dildo, a baby doll, along with a myriad other props necessary to poke fun at our slutball culture. For a while now, I have dressed up in a pink bikini and pumps so as to portray one of those annoying and loud cellphone girls I see now, everywhere in the city, screaming about sushi and shopping.

I don’t make much money doing this. My one paying skill has been writing for magazines and newspapers. And now I am watching the value of that one skill plummet like a condo in Florida.


The trip Dudester organized was truly cosponsored by TROJAN Brand Condoms, Gillette razors, and Cold-EEZE; and sounded so gross and crass and American, I had to go. I was tickled and repelled at the same time. Also the heat wasn’t working (again) in my apartment and would take days to fix because my insane, paranoid landlord had conveniently disappeared (again) after I paid him rent (in cash, again).

I knew this wasn’t going to be a glamorous vacation. In fact, it looked quite cheesy. Why did I want to go? Because I was invited. I have to say yes to everything. I don’t have the luxury to say no.

I am not a drug addict, I am not in a shame spiral, I don’t need to find the love inside myself. I am just poor. And a writer, stupidly. Instead of a brain surgeon or broker or reality show star I decided to become a writer. I have been doing it so long that I have developed no other skills so this is what I am. Now I was invited on a Mystery tour, into the weird new world of internet entrepreneurialism, where everything was an opportunity, and everyone was mysteriously cashing in.

The rest of The Junket is available for purchase on Amazon as a Kindle Single.