To tip or not to tip?

When I was deciding between two apartments in NYC, one in Manhattan and one in Fort Greene, I had a lot to consider. Did I want a view of the skyline from a fifth floor studio, or did I want to be in the skyline from the 15th floor? That kinda thing.

Though the apartments were very similar, one major difference was that the Manhattan building came with 24/7 doormen on staff (and it is all men, so I’m safe in the classification) and a live-in super. Friends who’d lived in doorman-less buildings saw that as the deciding factor right there. “You’ll never have to worry about getting a package delivered,” they said. And I could tell they were speaking from experience.

But now I’m in a pickle. A tipping pickle.

When are you supposed to tip your doorman? How often is often enough to stay in their good graces? If I tipped them each time they hand me my mail, each time they push the elevator button because they happen to be standing there, each time they open the door when they see me coming with my hands full of grocery bags, I’d have a doorman tipping budget bigger than my monthly cellphone bill.

Am I being stingy if I don’t tip all the time? Am I supposed to fork over a few bucks to each of them on a semi-regular basis? What’s expected? Are they looking at me with disdain when I walk by because I’m not tipping the way the old ladies who’ve lived here for decades do?

And what about the holidays? I’m already trying to figure out how to budget enough so they all get something. If I give each of them a decent holiday tip, I’ll be spending as much to cover their gifts as I do to get my own family their presents.

As I was getting settled, I had furniture shipped to me several times per week; once, a couple of the guys even used my spare key to bring the three huge boxes my 5-foot-tall dresser came in up to my apartment. I probably should’ve tipped them for that, huh? But they were off work by the time I got home, and I was broke because I’d just bought a 5-foot-tall dresser, and, well…I’ll try to make it up to them in their holiday gifts.