Take a tip from me

I heart New York as much as the next guy, but I've never mastered the whole tipping thing, which is such an important part of everyday life in that city.

(There's a reason they call it the Big Apple; everybody wants a bite.)

Oh, I'm fine in restaurants and bars. The waiter hands me a check, I figure the tip and deliver the correct amount. Better yet, I hand over a credit card and let somebody else do the math. I'm okay in cabs, where I can watch the clicking meter as I near my destination and do my calculations. And I almost always contribute to tip jars.

Where I fail is in the quick handoff -- the tips that reward doormen and bellhops and room-service waiters and shuttle drivers. There's that moment of social awkwardness where I say, "Thank you," then try to pass them a couple of bucks. I never know which hand to use or where to look or whether I'm tipping the right amount.

If I mess up the exchange, I feel like a goober. If it all goes smoothly, I still feel weird, like some gold-chain Vegas high-roller mobster type: "Here's a little something for your trouble, pal …."

I'm uncomfortable with the whole social convention. You help me with something, just doing your job, and I'm supposed to slip you some extra money? We're acting like friends -- "Let me help you with that bag, sir" -- but "thank you" isn't good enough. Suddenly, we're not friends anymore and it's strictly a commercial transaction.

Wouldn't it be more honest if the rate was set out at the beginning? "Let me help you with that bag for two dollars, sir." Ah, that would make it simpler, wouldn't it? "Hold the door open for a buck?" Gotcha. "Deliver your incredibly overpriced pot of room-service coffee to your door for only five dollars." Never mind, I'll stumble to Starbucks.

Even when I'm mentally prepared for the transaction, my money often won't cooperate. I have to unbutton a pocket, dig out my wallet, desperately thumb through it for the correct denomination. Is anything more inelegant than tipping somebody and asking for change? I know Tony Soprano would handle it smoother, peeling bills off a roll, saying just the right thing.

(Of course, Tony Soprano probably hands out twenty-dollar bills. That's typically all I have in my wallet because that's what ATMs dispense -- yuppie food stamps. Anything smaller ends up in the grubby hands of my kids.)

Tip recipients probably don't care how they get our dough, as long as we cough it up, but I can't get over the notion that they're smirking on the inside, watching the big gomer fumble with his money.

Maybe this discomfort stems from the fact that I've never been on the receiving end of tipping. I never worked in food service or at a hotel. I worked in a couple of clothing stores when I was in high school, then went right into the newspaper biz.

Now I work at home, all by myself, and it's not like I've got a reader looking over my shoulder, saying, "Whoa, nice verb! Here's a little something for your trouble."

I suppose I could put a tip jar on my desk in hopes that visitors would drop in the occasional buck. Might make a nice source of side income.

For my kids.