New York doesn’t have to be that hard—just ask Jake Dobkin


Resilient to gentrification, aggressively opinionated, and proud to a fault, native New Yorkers can’t help from imparting their wisdom to anyone, with or without this asphalt obstacle course embedded in their DNA.

Jake Dobkin, a lifelong New Yorker and co-founder of Gothamist, took this affliction a step further and recently wrote an entire book, Ask a Native New Yorker, based upon his long-running advice column of the same name. The new material expands upon the reader questions he fielded in his original columns and offers plenty of encouragement to stick it out. (If you make it a decade, he points out, you have what it takes to stay.)

I sat down with Jake and asked a few questions, one native New Yorker to another, about growing up in this city, change, and hometown pride.

What made you start the ‘Ask a Native New Yorker’ column?

I never realized my attitude problem could be harnessed. I’d talk a lot of smack to the younger employees and the editors said that could get some pageviews, why don’t you try writing it down.

At first it was super sarcastic, riffing on whatever. After I ran out of pure vitriol I switched to trying to be a little more helpful. I kept seeing these young writers get absolutely wrecked by New York and after two years they’d leave. New York is hard but it doesn’t have to be that hard. People just don’t know who to turn to when they arrive. Nobody knows shit about shit, the chance of meeting a real New Yorker and getting any real advice is pretty small, there aren’t that many of us, and we tend to be pretty tribal.

You never moved away?

One summer during college, 10 weeks in Spain was the longest I’ve been away. Salamanca and Madrid. The one thing New York doesn’t have is ancient ruins. [But] pretty only gets you so far. I would start to miss the action and all the stuff I love about it here. I’ve never felt bad about being trapped here.

You grew up in Brooklyn?

Park Slope.

What high school did you go to? We’re gonna have that New York conversation.

Oh, the status seeking ‘Who’s realer?’  Usually it’s the high school question, that’s how you tell. I went to public school, Stuyvesant. Binghamton for a turn, dropped out and went to Columbia.

What was your usual cut-off point? You know the whole, ‘Oh, I don’t go above 14th St.’ claim.

The old Stuyvesant was on 15th and 1st, so like 23rd St. The new Stuy was on Chambers, so…everything above 14th, especially on the West side was like ‘There be dragons.’ I remember one time when I was 15 a girl invited me to study at her apartment on the Upper West Side…Like all awkward teenage boys, I really would like to have gone…

Wow, you just tapped out? As a Brooklyn boy that was just ‘too far’?

‘What train goes there??? No! I can’t do it.’

What to you is the most painful shuttering in New York, other than Gothamist for that brief moment?

(Laughs.) I think the vitality of the city is in its constant reinvention and newness. Are there bars that I used to go to, dive bars in Brooklyn…this one place down on 9th St. by McDonald’s called CJ’s which was the dirtiest, cocaine-dealing-in-the-bathroom, dive bar I’ve ever been to. Now years later, I look back on it and sort of miss it. But, you know, that kind of nostalgia doesn’t get you very far.

Neighborhoods change so drastically…

When I was a kid Park Slope was much more lower middle class/working class, at least on my block. I miss those old families where it would be like, two elderly sisters and their crazy sons, one who works for corrections and the other is a car thief. Every house a crazy sitcom in it. Now, it’s like every house is owned by a single couple where one of them runs a hedge fund, and is a millionaire. An immaculate five-story brownstone by themselves.

It’s not like New York’s vitality has gone, it’s shifted around. Neighborhoods that used to be dead when I was growing up, like Gowanus, which is one neighborhood over, is now very vital. So maybe the action just moved, it didn’t die. So I don’t feel bad about it.

How deep into a conversation with another New Yorker is it appropriate to ask how much they pay for rent?

That’s a really interesting class conversation, you wouldn’t ask somebody how much they paid for their apartment, right? That would be like ‘Holy shit! That’s very intrusive.’ But somehow asking what somebody pays for rent is a lower level of nosey.

But it feels like a really common thing. People ask each other how much they pay for rent all the time.

Yeah, and you know that even when they don’t ask they’re Googling your apartment on Streeteasy. Every New York problem, ultimately if you follow it down the rabbit hole, leads to housing and how expensive it is. That’s why we’re all so stressed out and crazy. That’s why there are often no feelings of security for young people; everything ultimately is a housing issue.

Is housing or the MTA a bigger anxiety trigger?

The reason for so many MTA problems is you’re living three neighborhoods further out than you’d like—because of housing.

They build on each other. People who’ve never been here and see the MTA for the first time don’t understand why nothing is running, and they have to change trains four times. I’ve had to explain, ‘New Yorkers aren’t rude, they’re just really in a hurry.’ We’re just late all the time.

So late.

When you need to compose yourself and get away from the chaos of the city, what’s your go-to?

Rooftops. You’d be surprised how many of those ‘Do not open alarm will sound’ [doors] are actually disabled because supers like to go up on the roof to smoke. Pretty much every apartment I’ve ever been in, the rooftop has been an amazing sanctuary. A zen palace. A fortress of solitude.

How do you feel about fire escape ladders though?

I’m always a bit nervous about corroded fire escape ladders. At least once every few years, one collapses on pedestrians. When I was a younger and more adventurous kid we would do urban exploration on all these abandoned factories, I had a few very hairy scrapes where a fire escape ladder would start tilting backwards or you’d put your foot through…that metal is never as strong as it looks.

That’s definitely my major fear in New York. Other than the basement doors.

It’s the same fear though. Corroded iron.

Corroded iron and falling into New York oblivion. How has your relationship with New York changed being involved with local news?

Honestly, I feel like reporters are New Yorkers taken to the nth degree. Most New Yorkers are pretty sarcastic and unflappable. But a reporter, after listening to the police and fire lines for years, see every type of corruption and depravity at a clip that most people never have to ingest. Most people can ignore the news if they want for a few days, for almost 20 years I haven’t been able to. That does something to a person’s brain after a while. Sometimes I worry I’m becoming too jaded. On the other hand, the collection of people I work with, whether they grew up here or not, classic…just central casting New Yorkers and their crazy accents. 

What percentage of the office is native?

I’m gonna say less than 20% I can only think of one kid in the newsroom that I know is from New York. I mean, there are a lot of people from the area.They’re pretty New York. Most of them have lived in the city since college, but at some fundamental level, unless you’re truly native we cannot understand each other. We are separated by a vast chasm of history.

You have advice in your book about natives dating transplants, but can natives date natives? Cause I feel like there’s a certain friction.

That vast gulf of history is in some ways larger between me, who grew up in South Brooklyn, and somebody from Sunnyside Queens. I didn’t go to Williamsburg til I was 25…Queens was like a black hole.

But then again, my parents are from the Bronx, and lived happily in Brooklyn. I think New Yorkers, because of our cultural heritage of being a melting pot, we’re probably more flexible than we appear. But you have to be a certain type of person to be willing to date a native New Yorker. An exceptionally tolerant person.

It’s fantastic, I feel like when two natives get into a fight it’s an argument that nobody else can really decipher and…

It’s always so stupid. In the book, there’s this part that I talk about how New Yorkers always try to out real each other in terms of where they live like, “Oh, you’re from Park Slope? That’s not a real New York neighborhood. I grew up in Bushwick.” Yes, I will admit that your experience had elements that mine didn’t, but also you didn’t grow up around, let’s say, a thousand crazy communists. We can’t out New York each other. We must ultimately just respect each other’s New Yorkness.

What do you think is the most important thing to keep in mind, to keep you going here for the long haul? Is it just humor?

Yeah, obviously you have to have some humor for when you slip in garbage juice…but I think you just have to really be certain of the idea that even the worst year in New York is better than the best year anywhere else. Fundamentally, New York is the greatest city ever created, and probably ever will be created in the history of the world. And we are so lucky to get to live here.

How did it make you feel when Brooklyn became this trademark commodity on every T-shirt in the early 2000s?

At first it was really confusing. When I started at Columbia, Brooklyn was this whack backwater, the Manhattan kids made fun of you. And suddenly when I graduated, like 98-99, it was like ‘Oh shit! You’re from Brooklyn?!’ And Park Slope has never had the cache of say, Red Hook or Boerum Hill, but now, especially that I have kids, and all my acquaintances have kids, there’s a recognition [that it’s] fucking lucky. So then they say, how much do you pay for that apartment? And I say well, I get a little discount to market, but I do have to share a building with my parents. Which, you know…

Oh, that’s a very old school thing.

Yeah, we still do that thing where my parents live on the bottom two floors and me my wife and two kids live on the top two. And it’s like ‘Everybody Loves Raymond,” but with much crazier Jews.

That’s kinda nice, it’s a built-in babysitting element.

It is, if I trusted my parents for more than two hours with my kids. My parents are like hippies. They might just forget that they’re babysitting. Or I come home and it’s like midnight, and the kids are just watching inappropriate Netflix movies.

Were your parents smokers growing up?


Did you ever get sent to the store to pick up cigarettes?

No. They only smoked weed. And they got their weed from an uncle..well, my dad’s friend. He lived up in the Catskills and everyone said his job was rebuilding old barns…But his main job was the 200 acres of marijuana plants that he had..There was a closet in the house that was Cool Whip containers, there were 20 containers of weed just stacked up.

Who’s eating that much Cool Whip!?

I don’t know. That’s a really good question. Was there a Cool Whip factory nearby? Like maybe they got them for free? But it’s always Cool Whip. Anyway, they had more than enough.

I just remember being a kid and getting sent to the store by my dad. And that’s how I knew how much they cost. He’d just say get me a pack on the corner.

It was weird cause cigarettes were seen as really bad in Park Slope. Nobody smoked. My mom, she was a nurse, sometimes when she’d be visiting patients she’d get so stressed out she’d smoke in the car, and she’d never admit it. But weed..everybody’s parents smoked. It was totally normal. It was really confusing when we got the D.A.R.E don’t do drugs talk.

What’s your favorite memory of childhood in New York?

I have a lot of good memories of just running wild, unsupervised. Just throwing snowballs at cars and getting chased by drivers. We once shot out all the windows on the block with a BB gun, and then had to replace them. You know, it was a different time. In some ways the city was much more dangerous, but parents were much more chill. The idea that you’d be leaning over your kids to make sure they finished their homework was just not the environment that I grew up in. And I’m grateful for that. In some ways maybe we could’ve had some more supervision, but Park Slope was a great place to grow up.

Do you think it’s laughable that some people still think of New York as a very dangerous city?

Yeah. As a reporter, I know the stats. I always tell people, East New York, which is one of the most dangerous neighborhoods in New York, is now safer than the Upper East Side was when I was a kid.

What do you want people to understand about the book?

Some people think it must be a guide for new New Yorkers, and some of it is. There’s helpful advice for new arrivals, but a lot of it is topics that my native friends argue about. Like, what is the best slice of pizza? Or the correct way to ride on an escalator? And a lot of natives would enjoy reading the book, talking about how full of shit I am.

Oh, I saw your list of what every native should be carrying with them and I was like ‘Hand sanitizer?! I need to build my immune system!’ What is this hand sanitizer bullshit?

(Laughs.) Yeah, it’s true. There’s an essay in the book, ‘Should I wash my hands after I ride the subway?’ And I say no, New Yorkers don’t have to wash their hands after they ride the subway, because we don’t touch anything. (Laughs.) When’s the last time you touched something on the subway?

Yeah, you don’t even realize you’ve acclimated in that way. I had my niece on the train about a year and a half ago, she was about 11 at the time. And she was completely wrapped around the pole and pressed her face against it. She said, ‘What’s the problem?’

Kids don’t know…

I literally saw a woman gripping the pole with her asscheeks the other day. This is not a place to put your face EVER.

When you have little kids in New York they’ll throw themselves down on the pavement. You realize, native New Yorkers don’t get sick that much, we spend like 30 years getting exposed to like, Ebola.

We’ve gone through this renaissance and it seems people are now leaving, which I’m perfectly fine with, because rent is insane. What do you think is the next frontier for New York culturally?

New York state loses population, and NYC might even lose a little population, but we’re constantly revitalized by immigrants coming in. For thousands of immigrants from all over the world New York is still like a paradise [comparatively] and the place they’ve always wanted to be and they’re happy to settle here in all sorts of neighborhoods, and yeah, for upper middle class people who want very large apartments in Brooklyn Heights, maybe the ship has sailed. And, too bad. You know? But all four of my grandparents grew up in the Bronx,  some of them very poor. My mom grew up in the projects in the Bronx. If my grandkids move back to the Bronx, that’s not a net-loss for my family, that’s just the circle of life.

Did they pull rank on you about who’s more New York?

Sometimes when I talk to my dad and we’re arguing we’ll both start taking on the Brooklyn accent, in his case the Bronx accent, his is a little more genuine than mine. And all of his friends, who are all from the Bronx, when they get going, yelling at each other, especially when they drink, it sounds like a David Mamet play. Like Archie Bunker. Comically florid accents.

Do you think the New York accent is dying out?

No, I think it’s changing. The accent we think of as the New York accent is actually a regional accent that’s kinda Italian and Yiddish, and a little Irish, maybe. It’s essentially the midcentury accent, of those groups coming over and blending together. Now, the accent is probably a Spanish accent, or Polish, or one of the African languages. So it’s gonna change. When our kids think of the New York accent they’re not gonna think of what we think of. It’s a living thing, it evolves constantly. Which is great, it’s how it’s supposed to be.

I’ve seen these sweatshirts that say ‘New York is a Nationality.’ How do you feel about that sentiment?

I’ve always felt that we should secede and join the EU, or Canada, cause New York at this point has much more in common with foreign places than any state in America, except maybe California. The gap gets bigger and bigger between us and the rest of the state, the rest of the country. When I’m really depressed, thinking about Republicans taking over the federal government, it’s bad and terrible for a lot of people but there are times when I think honestly, New York and California keep getting more liberal and more Democratically controlled. When Trump was elected it probably secured the Democrats control of New York for a thousand years. It’ll be a shame to lose the rest of the country, but I never go there.

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