Someone somewhere at some time wrote the rules of tipping. Someday something will drive me to study said rules. Until then, I blunder forward in ignorance.

A little person (I don’t know what is the politically correct term; I just know I can’t say dwarf or midget) packed my groceries last week. She was so short she could barely get the bags into the boot of my husband’s SUV. So I ended up helping her.  Short on change (no pun intended), I gave her all I had – the magnificent sum of TT$3 (US 50 cents). She gave me a look, which quite clearly registered her disdain, and I shrank to two foot six.  Sheepishly I got into the car and drove off feeling guilty. I had committed a tipping offence. I am a repeat offender.

A few years ago I shared a van from Toronto’s Pearson Airport to my hotel downtown with other travellers. At my destination I offloaded some Canadian coins my father had given me on the van driver. He studied them, looked up at me and remarked sarcastically “Haven’t seen one of those for a while!” Oh, the shame…

I have a vivid memory of exiting a London black cab aged 11 or so with my mother and hearing the cab driver shout at my mother ” Don’t you people give tips?!” That sharp rebuke stung me to the core and left me with a morbid fear of being considered cheap because I am black.  I’ve gone so far as to apologise to taxi drivers when I don’t have enough money for a tip. But is an apology enough? Is it ok to express your regret and move on, leaving the other party disgruntled? Or should I hand over my vex money and hitchhike home?

When it comes to dining I firmly believe it is unwise to piss off the wait staff, particularly if you intend to visit the establishment again. Bad tips leave bad memories.  I’m convinced an uncomfortably large number of disenchanted wait staff would cheerfully leave a DNA imprint in my entree should I be regarded as miserly.

My husband, who clings to a dollar tighter than Cersei Lannister holds onto a grudge, thinks differently. As far as he’s concerned, people are paid to do a job. What do they need tips for? I try to always leave something. Memories of that cab ride haunt me.

I live in a country where tipping is the exception rather than the norm, so I am always a bit flustered when persons demand a tip. On a recent trip to Panama, a taxi tout actually chased my husband and I to the car and opened the door to demand his reward for pointing us in the direction of the taxi stand.  Fearing cab cartel reprisal I hastily handed over five bucks.

Contrast the Panamanian tout’s attitude with my T&T experience last month in the car park of a doctor’s building. After helping me fold my mother’s walker and get her into the car in pouring rain, the security guard refused a tip, insisting I was making him feel guilty for doing his job.  I cannot win.

Why can’t Trip Advisor or Lonely Planet publish Country Tipping Tips? That would prevent idiots like me from annoying the natives. Who to tip? When to tip? And how much? I’m not ashamed to admit I need help distributing small change.

Until the Tip With Confidence bible is written, perhaps you guys could help me? Share your tipping advice and mishaps in the comments below. You have to be better at this than I am.