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Ask a Native New Yorker: Hard-Earned Advice on Surviving and Thriving in the Big City
Ask a Native New Yorker is Jake Dobkin’s essential guide to the Big Apple’s culture, people, and lifestyles.
As a third-generation New Yorker who was born, bred, and educated there, Jake Dobkin was such a fan of his hometown that he started Gothamist, a popular and acclaimed website with a focus on news, events, and culture in the city, and Ask a Native New Yorker became one of its most popular columns. This book version features all original writing and aims to help newbies evolve into real New Yorkers with humor and a command of the facts.
In 48 short essays and 11 sidebars, the book offers practical information about transportation, apartment hunting, and even cultivating relationships for anyone fresh to the Big Apple. Subjects include “Why is New York the greatest city in the world?,” “Where should I live?,” “Where do you find peace and quiet when you feel overwhelmed?,” and “Who do I have to give up my subway seat to?”
Part philosophy, part anecdote collection, and part no-nonsense guide, Ask a Native New Yorker will become the default gift for transplants to New York, whether they’re here for internships, college, or starting a new job.
Includes black-and-white photographs
As a third-generation New Yorker who was born, bred, and educated there, Jake Dobkin was such a fan of his hometown that he started Gothamist, a popular and acclaimed website with a focus on news, events, and culture in the city, and Ask a Native New Yorker became one of its most popular columns. This book version features all original writing and aims to help newbies evolve into real New Yorkers with humor and a command of the facts.
In 48 short essays and 11 sidebars, the book offers practical information about transportation, apartment hunting, and even cultivating relationships for anyone fresh to the Big Apple. Subjects include “Why is New York the greatest city in the world?,” “Where should I live?,” “Where do you find peace and quiet when you feel overwhelmed?,” and “Who do I have to give up my subway seat to?”
Part philosophy, part anecdote collection, and part no-nonsense guide, Ask a Native New Yorker will become the default gift for transplants to New York, whether they’re here for internships, college, or starting a new job.
Includes black-and-white photographs
- GenresNew YorkTravelNonfiction
256 pages, Hardcover
Published March 12, 2019
27 people are currently reading
170 people want to read
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Displaying 1 - 21 of 21 reviews
December 3, 2019
I have mixed feelings about this book. I am not a Native New Yorker, though have lived here long enough to be considered a Real New Yorker according to the author. Perhaps it's just that my experience is different than the norm, having moved here as an adult with a child, but so many things don't ring true for me. Do I love New York? Yes. Do I think there's no other place in the rest of the the world as fantastic? Not really. I see this best place in the world attitude with a lot of Native New Yorkers and personally find it quite humorous. They consider themselves quite worldly and they think their opinions are correct because they are so worldly, but when push comes to shove, they know very little about life not only outside of New York but outside of their own tiny neighborhood. I understand that this book is meant to be humorous, though personally I didn't find it that funny, but really it comes off as very patronizing. Most transplants I know have experienced vast swaths of the City that a Native New Yorker has never even heard of. Most transplants I know, myself included, love leaving their own neighborhoods to explore other places in the City. And obviously these transplants have, at some point in their lives, managed to live elsewhere. Most of the Native New Yorkers I have known barely leave their own neighborhoods, especially those who live in Manhattan. They definitely don't have much interest in exploring the so-called outerboroughs. They have little desire to leave New York to experience the rest of the country (West Coast excluded) or the world (Europe or Israel excluded). Obviously this book is meant as some sort of love song to New York but the tone certainly would not have convinced me to move and stay here, had I read it over a decade ago when I was considering it a a potential place to settle. Yes, New York can be a tough place to live but it seems to me that basically the theme running through this book is just be tough and it will be ok. Let's just say that being tough isn't going to help anyone succeed without some cash to back it up. Which leads me to my last point. This book is written from a very privileged point of view. The author's experience of growing up as a white, Jewish boy in Park Slope and going to one of the best high schools in the country is vastly more privileged and therefore vastly different that the experience of, say, a Native New Yorker who also happens to be a minority boy growing up in Red Hook. The author's parents owned a home in Park Slope where the author could move back and save money for his future home. I'm guessing that this is a very different experience than the minority kid growing up in a NYCHA building in Red Hook has. I know this is a vastly different experience than most transplants have, even those who are doing relatively well financially.
There were things I liked about the book, don't get me wrong. For instance, I love to ride a bicycle in New York, which the author mentions a few times as a good means of getting around. I enjoyed his anti-car bias and his view on the state of climate change. I enjoyed when his love affair with New York had a less superior and cynical voice.
I'll end with this, if you're considering a move to New York, don't approach it like you're moving to some magical fairy land but also don't approach it like it's the hardest place in the world to succeed. It is a hard place to live, just like many other places in the world and the country but it's not like try to survive in, say, Kolkata! If you move and decide that it's not for you, unlike the author insinuates, you haven't failed. You've succeeded because you realized that there's somewhere else in this world where you can be happier and you've chosen to go chase that place down. In my book, that's winning at life, not losing.
There were things I liked about the book, don't get me wrong. For instance, I love to ride a bicycle in New York, which the author mentions a few times as a good means of getting around. I enjoyed his anti-car bias and his view on the state of climate change. I enjoyed when his love affair with New York had a less superior and cynical voice.
I'll end with this, if you're considering a move to New York, don't approach it like you're moving to some magical fairy land but also don't approach it like it's the hardest place in the world to succeed. It is a hard place to live, just like many other places in the world and the country but it's not like try to survive in, say, Kolkata! If you move and decide that it's not for you, unlike the author insinuates, you haven't failed. You've succeeded because you realized that there's somewhere else in this world where you can be happier and you've chosen to go chase that place down. In my book, that's winning at life, not losing.
May 20, 2019
As a native New Yorker, my biggest question picking up this book was "will this be something I can give to friends?" Short answer: ABSOLUTELY.
LIKED: There is a lot of really good advice in here for someone who is either visiting NYC or going to live in NYC. Even if you've been living in NYC for 10yrs -- you should read this. Because anyone who didn't grow up on these streets could absolutely benefit from a lot of this info. There are some things you just look at/experience differently when you grow up here, and this book speaks to a lot of that. If you aren't molded by NYC from a young age you miss out on a lot of the instincts that those of us who are born on the streets (A METAPHOR) have.
DISLIKED: The only thing that I, again, AS A NATIVE NEW YORKER have as a pet peeve is when people refer to ALL corner stores as bodegas. A bodega is a corner store in a latino community. If you are not in a latino neighborhood, then it's just a corner store, or simply "the store." I feel like that is such a common error that drives me absolutely nuts. Even people in the yuppiest neighborhoods, like Park Slope, call their corner stores bodegas and it baffles me. Just say "the store" and we will know what you mean.
LIKED: There is a lot of really good advice in here for someone who is either visiting NYC or going to live in NYC. Even if you've been living in NYC for 10yrs -- you should read this. Because anyone who didn't grow up on these streets could absolutely benefit from a lot of this info. There are some things you just look at/experience differently when you grow up here, and this book speaks to a lot of that. If you aren't molded by NYC from a young age you miss out on a lot of the instincts that those of us who are born on the streets (A METAPHOR) have.
DISLIKED: The only thing that I, again, AS A NATIVE NEW YORKER have as a pet peeve is when people refer to ALL corner stores as bodegas. A bodega is a corner store in a latino community. If you are not in a latino neighborhood, then it's just a corner store, or simply "the store." I feel like that is such a common error that drives me absolutely nuts. Even people in the yuppiest neighborhoods, like Park Slope, call their corner stores bodegas and it baffles me. Just say "the store" and we will know what you mean.
Want to read
March 11, 2019Guhhhh I have such complicated feelings about Jake Dobkin, but holy god I want to read this IMMEDIATELY.
February 27, 2020
Started reading this book to get some tips on navigating through the city of New York, not realizing that it'd end up becoming one to provide tips on navigating through life! Jake Dobkin really does provide deep insight into everything from interesting spots in the city, lifestyle choices in New York to life choices like friendship, becoming a parent, dealing with challenging careers, personal lives, dating issues, marriages and so on (I'm sure I'm missing something.) There's something for everyone in this book! The format of the chapters is interesting and the writing, wise yet hilarious, a rare combination very few authors can ace.
December 28, 2019
I do balk a little at the idea of an upper middle class white man being the authority on New York City, and I think that identity does come across negatively a few times (encouraging someone who's on the fence to go ahead and take the finance job, a cavalier attitude about being ticketed by police, a relative lack of specificity about outer borough neighborhoods and how other ethnic groups experience and shape the city); the vastness and diversity of New York probably lends itself to a more multi-faceted "Ask a Native New Yorker" concept, where a more varied team of Native New Yorkers might answer these questions and aggregate their responses.
That being said, if you're willing to accept the premise of the book, the advice is pretty sound and it's an enjoyable, amusing read that does match up with my experience as a Native New Yorker--especially when it comes to dispelling the idea that New Yorkers are rude and that the city is unlivable. It also embraces a pro-New York chauvinism that often turns off outsiders and feels completely in line with my own beliefs and those of most native New Yorkers I know.
That being said, if you're willing to accept the premise of the book, the advice is pretty sound and it's an enjoyable, amusing read that does match up with my experience as a Native New Yorker--especially when it comes to dispelling the idea that New Yorkers are rude and that the city is unlivable. It also embraces a pro-New York chauvinism that often turns off outsiders and feels completely in line with my own beliefs and those of most native New Yorkers I know.
August 20, 2021
This book is full of many good tips for navigating New York, understanding New Yorkers, and dealing with all the special kinds of trials that only come from the big apple. I enjoyed most of the book and its many anecdotes, though some sections were burdened by a heaping helping of condescension that doesn't make NY natives look great. Still, as someone moving to NYC for a job very soon, I liked hearing Jake's advice.
August 16, 2025
I’m not sure why I thought this, but I thought this was going to be a satire. It was not. It’s a book composed of people writing in to the author about all things New York City and his very opinionated, very long responses to said questions.
This is sort of hard to review as a whole. Some of his guidance was pretty sound and others the author came across as really pretentious and condescending.
This is sort of hard to review as a whole. Some of his guidance was pretty sound and others the author came across as really pretentious and condescending.
April 19, 2022
Reading this book as a New York City native, I'm happy to report that a good portion of the wisdom Dobkins bestows upon readers is relatively accurate. Some of the boundless optimism and blind allegiance to the city is easy to call into question given the recent rise in crime and failed resurgence following coronavirus lockdowns, but it comes from a good place.
As with all advice delivered with such gusto and confidence, take it with a grain of salt. I'll agree that living in New York City is an experience like no other, but falling blindly in love with it like Dobkins implies you should isn't the best idea. At the end of the day, it is just a city. It's very likely the best city in the world, but it's still just a city.
There's also a small pinch of anti-conservative rhetoric that doesn't really need to be here, but thankfully this isn't as prevalent an issue as it tends to be in other books that include it.
If you're someone moving out to the Big Apple, the book is a fairly accurate guide of what to expect and how to survive. Even for natives, it serves as a bit of an opportunity to reflect on the good, bad, and sometimes absurd aspects of the city we've known our whole lives.
All in all, it's a fun read.
As with all advice delivered with such gusto and confidence, take it with a grain of salt. I'll agree that living in New York City is an experience like no other, but falling blindly in love with it like Dobkins implies you should isn't the best idea. At the end of the day, it is just a city. It's very likely the best city in the world, but it's still just a city.
There's also a small pinch of anti-conservative rhetoric that doesn't really need to be here, but thankfully this isn't as prevalent an issue as it tends to be in other books that include it.
If you're someone moving out to the Big Apple, the book is a fairly accurate guide of what to expect and how to survive. Even for natives, it serves as a bit of an opportunity to reflect on the good, bad, and sometimes absurd aspects of the city we've known our whole lives.
All in all, it's a fun read.
July 3, 2019
If I could give this zero stars, I would.
Blog books and I generally don't get along. There are some exceptions, Vanishing New York: How a Great City Lost Its Soul gave me better context for and appreciation of the blog of the same name. I enjoy Gothamist but not always the Ask a Native New Yorker column, and this book did nothing to help that. It's about 10% semi useful advice that is in no way unique to Gothamist or Dobkin and 90% snark on non natives. There is a book to be written about advice for transplants, but this isn't it. While he tries to dispel some myths about New Yorkers not being friendly, he counters that by coming across as a total jackass in some "advice" like his arbitrary delineations for how far/long you can still move and not be native. I acknowledge some of it was probably meant to be humor, but it really didn't come through.
Blog books and I generally don't get along. There are some exceptions, Vanishing New York: How a Great City Lost Its Soul gave me better context for and appreciation of the blog of the same name. I enjoy Gothamist but not always the Ask a Native New Yorker column, and this book did nothing to help that. It's about 10% semi useful advice that is in no way unique to Gothamist or Dobkin and 90% snark on non natives. There is a book to be written about advice for transplants, but this isn't it. While he tries to dispel some myths about New Yorkers not being friendly, he counters that by coming across as a total jackass in some "advice" like his arbitrary delineations for how far/long you can still move and not be native. I acknowledge some of it was probably meant to be humor, but it really didn't come through.
January 15, 2022
Probably closer to 3 1/2 stars
This book reiterated the sentiment on the little zipper bag I bought near Chelsea Market - “I wish I could afford to live in New York “.
Without a really nice chunk of change there is no way I could survive living in NYC.
This book reiterated the sentiment on the little zipper bag I bought near Chelsea Market - “I wish I could afford to live in New York “.
Without a really nice chunk of change there is no way I could survive living in NYC.
July 23, 2019
As a Native New Yorker born and bred I found this book to be highly amusing and accurate (Though the extent to which he advises to go to local government for help seems a bit high compared to reality).
I'm unsure however of how helpful it would be to someone actually trying to navigate these turbulent waters. And gifting it to someone who might find it useful almost seems patronizing. In other words, the demographic for who would read this book seems small.
I'm unsure however of how helpful it would be to someone actually trying to navigate these turbulent waters. And gifting it to someone who might find it useful almost seems patronizing. In other words, the demographic for who would read this book seems small.
March 27, 2021
I thought these questions were great to read about because I've also wondered the same thing. Some of the advice he gave was good advice.
I always wonder how people survive and thrive in New York City and this book answered that.
I always wonder how people survive and thrive in New York City and this book answered that.
December 9, 2021
This book was given to me by a friend and as I am nearing my 6 month mark of living in NYC, there was a lot of tips and tricks that I will start applying to my life here going forward. Wish I knew about it sooner!
June 10, 2025
Subjective Opinions and advice
The author is definitely a NYC lover. He loves NYC too much that sometimes i think his advice is too subjective. Of course, there are no absoulte right or wrong for his advice. Readers just need to assess them carefully
The author is definitely a NYC lover. He loves NYC too much that sometimes i think his advice is too subjective. Of course, there are no absoulte right or wrong for his advice. Readers just need to assess them carefully
August 31, 2019
If you've recently moved to New York City this is a helpful, funny, and easy to read guide to thriving in your new home.
January 28, 2022
Bloggy book with information easily found online.
September 26, 2022
Cheeky and cute. I bought it on my last trip to NYC because I wanted something that actually represented NY. I loved it but I also LOVE NY so I may be bias
November 25, 2022
As a Native NYer, I adore this book for its straightforward counsel and humor.
January 11, 2024
Has all the street smarts... with a side of ego
February 21, 2025
Listened to the audiobook, a fun way to learn about an old city that is an iconic part of our country.
September 24, 2025
Possibly my favorite non-fiction book on NYC so far. Contains thoughtful insights about what has made this city great and how this city will continue to soar even if people wish it doom.
Displaying 1 - 21 of 21 reviews