What Would You Do? : Tip Drill

[Editor's Note: Relax, this ain't another ode to black women's booties, nor does it have anything to do with that infamous Nelly video.]

I was in New York City on bidness yesterday, and as with any trip to a modern metropolis, this means needing spare money on hand for tips. Growing up, my folks never really took us to places to eat where tipping was necessary. With 3 boys, it's no wonder we usually ate out at places where you ordered your food standing up, not sitting down. I didn't learn about tipping until I was well into the professional world and summarily got myself embarrassed by colleagues when the check came. I quickly gained a reputation as a lousy tipper, which sorta peeved me because I didn't know better, but I was raised better. Now, I usually tip 20% or so for most meals, assuming the service was up to par. Folks waiting tables only make $3/hr, so don't be a tightwad. Pay the folks.

Anyways, today's edition of What Would You Do? focuses on a handful of gratuity-related situations I encountered today alone in the Big Apple.

#1 Unnamed Hispanic Shoeshiner - After getting off the Acela in Penn Station, I decide to cop a shoeshine before I hit my destination. My black Kenneth Cole slip-ons have seen better days, and while my Pops taught me a lot of stuff growing up, keeping shoes spiffy is a lesson I regrettably slept through. I'll willingly admit my shoes sometimes look turned the eff' over, when reality is they just need a little refreshing. So, I find a storefront spot just below the escalator to MSG and have a seat. The shoeshine cat clearly doesn't speak a word of English, so I dig deep in my Hood Spanlish' translation guide and mutter a warbly "cuanto es?". "Quatro." He replies. I nod my head and dude goes to work. {pause}

5 minutes later, the shoes don't just look good, they look freakin' awesome, prolly even better than the day I bought them. I mean seriously, the shoes look so good I half wanna take a camera phone pic and send it to my wife who seems to clown me everytime I slide them on. I mean, seriously, it's a great job.

So, how much money should I tip Unnamed Hispanic Shoeshiner for his services?

#2 Extra-Friendly Moroccan Obama-Supporting Cabdriver - After I get off the W train, I catch a gypsy cab in Queens. As is customary, these cats don't have meters, nor do they usually have set fees for typical destinations. You can, and should negotiate what you're willing to pay before the ride begins.

Most New York cabbies aren't gonna win a Mr. Congeniality award anytime soon. In the past I've had cabbies who damn near assaulted me verbally for merely asking them to acknowledge that they heard me when I told them my desired destination. Things have gotten a lot better of late, now the cabs in Midtown even have interactive video screens in the rear with a pretty cool internet news feature. But that doesn't make the cabbies any nicer. This is fine, I'm from the South and I like a good convo as much as anyone else, but I can do without just as easily.

Anyways, I hop in the Towncar, and the driver happens to be a brother with a thick foreign accent. I tell him my destination and he says "$12... $15... $35... whatever you want to pay, my brother!."

"$12!" I reply sternly, letting dude know I'm not playin' no shell games with the fare.

"Cool my brother. Let's go!"

Dude proceeds to drive me to my destination with the utmost care, talks politricks ("Obama. He is the man!") and business ("The Big Three, they would get nothing in my homeland."), tells me about his native Morocco, and is generally the best part of my very difficult day. If I didn't know any better, I'd swear I was in NC riding a Riderside Cab.

When we arrive at LaGuardia, the guy doesn't even try to swindle me, although I was more than prepared to go to war if necessary.

"$12 my brother!"

I'll admit, I was so impressed with the cabbie that I wanted to give him a tip. The question is, how much?

#3 Helpful Ethiopian Avis Woman - At last, I make it to my final destination of the day, and at the airport the Avis guys have my car ready when I arrive. Unfortunately, they gave me the biggest piece of automotive crap on the road today, the vaunted Pontiac SunFire. Ya'll know how I hate Pontiacs. My days been bad enough, and I wouldn't usually make a fuss of this sorta thing, but after a shaky flight and having awoken at 5am, my patience is thin.

It head to the rental office and not-so-nicely ask for an upgrade since the SunFire is on my Avis profile as I car I should never be assigned. If this sounds a bit trivial and a little picky/b*tchmade to ya'll, try spending a majority of your working days in a rental car and tell me if you don't develop a bit of a nagging preference.

Anyways, although I'm hardly nice, the Ethiopian sista behind the counter understands my agitation and immediately swaps my Pontiac Matchbox® car for a cool GMC Envoy.

Man, do I love Africans! But how much should I tip the sista for hooking me up?

Question: How big a tip should the Unnamed Hispanic Shoeshiner get in addition to his $4 service? How much should the Extra-Friendly Moroccan Obama-Supporting Cabdriver get in addition to his $12 fare? Should I slide the Helpful Ethiopian Avis Woman for hooking me up with a real car? Does how well you tip those who serve you say something about your respect for others? Have you even gotten notably bad service and been conflicted about tipping?