Dear Urban Diplomat: Do I really have to tip for takeout?

Dear Urban Diplomat,
Every day, I visit a café near my office to get a takeout lunch, usually a bottle of water and a veggie sandwich from the refrigerated display. When prompted by the debit machine, I always skip the tip because, well, I’ve done all the work. Here’s the thing: whenever I pay, I notice the staff behind the counter giving me dirty looks, clearly because of my no-tip policy. Should I really be tipping even where there’s no service to speak of?
—Gratuitous Silence, Midtown

A tip should be awarded only for good service, so you’re technically off the hook, but try to see it from the staff’s perspective. They’re probably making minimum wage, scrambling to earn a post-pandemic income. In a sense, they are providing a service by opening up the shop, stocking the fridges, cleaning the floors and taking out the trash. If you can afford it, tip next time. If you can’t, learn to live with the glare.

Dear Urban Diplomat,
About a month ago, I got rear-ended by my next-door neighbour, an elderly woman. Nothing major, just a bit of damage to each vehicle. When I suggested that we go through insurance to fix my bumper, she begged me to pay with cash, fearing she would lose her licence. I agreed, partly out of sympathy, partly to avoid the headache of dealing with insurance people. I paid $1,200 in cash with the assumption that my neighbour would reimburse me. But, every time I approach her, she mumbles something vague about the money arriving “soon.” Then nada. What’s the best way to handle this without putting her licence, and independence, in jeopardy?
—Hit and Run, Guildwood

Kudos for being so neighbourly. A lot of people would have gone straight through insurance with little consideration for the lead foot next door. But nice people can get taken advantage of, even by little old ladies. To make things more manageable for your neighbour, offer her the option of paying the debt in monthly instalments. Be sure to set a hard deadline. And, if she still doesn’t deliver, ask kindly but firmly for her insurance information.

Dear Urban Diplomat,
I’m a young hairdresser trying to build my clientele at a salon in the west end. My clients often spill about their personal lives, which makes me feel like their de facto therapist. One particular client recently revealed that she’s cheating on her husband—and having the time of her life doing so. She’ll give me updates during our monthly appointments, and I’m routinely horrified by her behaviour. I’d like to drop her as a client, but I need the money. Any advice?
—Can’t Cut It, Lambton

In any profession, you’re bound to encounter people you find morally deficient, whether it’s the anti-vaxxer at the office or the philanderer in the salon. It’s part of making a living and getting along in the world, so this is a good exercise in learning to coexist. The next time she launches into a monologue, steer the conversation elsewhere: work, friends, the latest Netflix release. The best stylists are adept raconteurs, so consider this an opportunity for professional development.

Dear Urban Diplomat,
Ever since university, I’ve been a big drinker, and booze has always been beneficial to my work life—I take my clients out on the town, and I close more deals than my non-drinking colleagues. But my wife is pregnant, and we agreed that I would go sober in solidarity until the wee one arrives. It’s now been three months, and I’ve noticed a huge drop in my ability to close deals. Have I made a horrible mistake?
—Off the Sauce, Davenport

Earning a consistent income in this economy is important, especially with a baby on the way, but maybe your wife is trying to tell you something about your drinking habits. Talk to her about the financial fallout of your sobriety. If her request was really about solidarity—and not about the state of your liver—she may let you off the hook. Even if she doesn’t, you only have six months to go.

Send your questions to the Urban Diplomat at urbandiplomat@torontolife.com