Are you relatively new to this bustling metropolis? Don't be shy about it, everyone was new to New York once upon a time, except, of course, those battle-hardened residents who've lived here their whole lives and Know It All. One of these lifers works among us at Gothamist—publisher Jake Dobkin grew up in Park Slope and still resides there. He is now fielding questions—ask him anything by sending an email here, but be advised that Dobkin is "not sure you guys will be able to handle my realness." We can keep you anonymous if you prefer; just let us know what neighborhood you live in.

Dear Native New Yorker:

I find your city's holiday tipping practices to be a perplexing ordeal. Where I come from, a holiday tip was a plate of cookies or a thoughtful card. But here, it seems like every single service professional you interact with has an expectation of some year end palm-greasing. I get that you've got to tip your super if you want to get your sink unclogged next year. But where does it end? Do I have to tip my Laundromat lady? What about the guy who cuts my hair? Doesn't he get like a tip already for each cut? What about all the city employees, like the mailman who lugs all my Amazon packages, or the garbagemen who took my old mattress away?

Please give me a simple rule to follow and ballpark suggested amounts so that I can move on with my life.

The Grinch Who Sucks at Tipping

Jake Dobkin has kicked this week's question to Jen Chung, who keeps records (okay, her husband keeps records) of holiday tips for her building dating back to 2006.

The short answer is yes, you should tip everyone who has made your life easier and more pleasant over the year. Your apartment's garbage doesn't get to the sidewalk by itself!

Obviously, there are some real variables, like how generous you can afford to be this year and who to include. But here's the rule: If you receive regular service from someone who seems potentially underpaid, you should tip them, unless you tip them regularly already, or tipping is specifically forbidden. However, tips should be kept proportional to the amount you pay for the service and your own ability to pay.

Figure out how much you can spare for a total tipping budget (which might not be easy, given all your other holiday spending). Then create a list of people you'd like to tip, prioritizing the most important people and work from there.

For those who live in smaller buildings, you could give your super around $40-100, and, if you have one, give a porter $20-60. Obviously you know who does the actual dirty work, who fixed that leak quickly—you can adjust the amounts accordingly.

If you live in a bigger building, some more thinking/budgeting is required. Last year, a friend of mine moved into his first doorman building and was overwhelmed by having multiple people (doormen, porters, super, etc.) to tip. Think about how many deliveries you get, how many times a year you have friends over, do they hold your mail, do you vomit in the hallway, do you secretly Airbnb your apartment and need to stay on their good side, etc.

If you don't tip during the year, and you have multiple people in the same building to tip, I think something between $30-100 per staffer is great. For higher-maintenance residents, with dry cleaning deliveries, grocery deliveries, packages and so on, you should give more. Feel free to give little extra to building staffers who may have been exceptionally helpful during the year.

Brick Underground's exhaustive tipping guide is very helpful, with more suggestions for other categories:

- Cleaning person/housekeeper: One to two weeks of pay.
- Cleaning service: Tip 15 to 20 percent throughout the year, as a portion of their earnings goes to the cleaning service. If the same crew cleans your apartment each time, a holiday tip (one week) is appreciated.
- Full-time nanny: One week's pay minimum, or two if you can afford it. Or, one week's pay and one week's vacation.
- Regular babysitter hired occasionally: Consider $25 to $50 in cash or a gift card
- Regular dog walker: One week's pay
- UPS delivery: Since UPS assigns drivers to specific addresses, $25 to $50 if you have a lot of packages delivered. More if you have a lot of business-related deliveries.
- Mail carrier: By law, mail carriers can't accept cash or anything worth more than $20. In reality, some (but by no means most) residents do tip in the $25 to $50 range, especially if they receive a lot of deliveries or a lot of mail that requires signatures. For a fuller discussion of the postal carrier tipping question, click here.

Also consider giving a tip to some other important people—like your dry cleaner (some of us have very serious dependencies on reliable dry cleaners!); a manicurist (seriously, tip them well); a hair stylist if you're not tipping during the year ($25-50); newspaper delivery person ($20; yes, some of us still get newspapers); personal trainer (cost of one session); the coffee cart guy who is there through the hot days, the bitterly cold days and times in between ($20); the parking garage attendant ($20-$25).

Invest in those holiday tip money cards and write a brief note, like "Thank you for everything you've done this year!" and sign your name; include your apartment number if it's for a building staffer.

Local militant (and notably generous holiday tipper) Jake Dobkin says, "Remember, tipping is only necessary because capitalism exploits certain classes of workers-minorities, the working poor, those with the least ability to organize. The practice allows the relatively well-off to feel less guilty about their place at the top of the pile, and allows the oppressed workers to be slightly less immiserated around the holidays, but it’s no replacement for revolution. Or, at least, the support of policies that would help the working poor, such as a higher minimum wage, and national paid sick leave."

Also, apparently you have until February to give holiday tips, so if you're strapped for cash now, a tip will still be appreciated in a few months.