Dear Urban Diplomat: My buddy owns an Italian restaurant on the Danforth. Should I lend him money?

Dear Urban Diplomat,
A buddy of mine owns an Italian restaurant on the Danforth, and business has been predictably slow. Recently, he reached out to ask if I would be willing to lend him $10,000 to help him stay afloat during the winter, with a promise of 10 per cent interest once sales increase again. Our friendship aside, I can’t help but feel like this is a bad investment. Thoughts?
—Cheque, Please, Upper Beaches

Even if your buddy makes the best bolognese in town, businesses centred around indoor dining are unlikely to thrive in the near future—at least not until everyone gets a double shot of vaccine. That said, friendship is measured during times of hardship—not prosperity—and it sounds like your pal needs you now more than ever. If you’ve got the extra cash to spare, do it, in exchange for the aforementioned interest and a lifetime supply of lasagna. But be prepared for it to be a money-losing venture.

Dear Urban Diplomat,
I went to the LCBO last week to buy some wine for a holiday Zoom party. At the checkout, the cashier asked me to remove my mask to verify my identity. I’m 57 and haven’t been carded since the early ’90s. I begrudgingly obliged, just to get on with my day, but requiring me to remove my mask indoors seems like a moronic policy. So I made sure to give the cashier a piece of my mind on the way out. Was I way out of line?
—Mask Ask, Rexdale

Even with a life-threatening virus in our midst, verifying identification still falls under the LCBO’s security protocols. The purpose, of course, is to prevent every teenager in the province from borrowing their older sibling’s ID to get liquor. Given your advanced age, this sounds like it was an overzealous application of the policy, so I don’t blame you for being annoyed, but maybe take it up with the ombudsman next time, instead of a front-line worker.

Dear Urban Diplomat,
My mother has been getting those asymptomatic Covid-19 tests at Shoppers at least once a week, claiming (falsely) that she needs them because she’s visiting a relative in long-term care. Instead of just staying home and self-isolating like the rest of us, she’s using the consistently negative results to mitigate her anxiety about the virus. It’s clearly become a compulsion. What should I do?
—Negative Reinforcement, North York

The government is paying Shoppers $42 for every test, so your mother’s neurosis is costing taxpayers a tidy sum. Her actions are wrong for a couple of other reasons: lying on her questionnaire, taking away slots from others, wasting the communal swab supply. This little ruse needs to stop immediately. Buy her a handheld thermometer gun so she can easily monitor for symptoms at home. And get her an apocalypse-worthy stock of masks and sanitizer—anything to keep her physically and psychologically safeguarded against the virus.

Dear Urban Diplomat,
My friend, a lifelong slacker, got fired from his job a couple of months ago because of poor performance, not for anything related to Covid-19. Still, he applied for CERB, with, from what I can tell, no intention of finding a job anytime soon. He already collected both rounds and said the government will probably never find out because they have such a glut of applications to process. It’s obviously wrong on so many levels. What should I do?
—Unemployment Benefits, Little Italy

As the old saying goes, there’s no such thing as free money—and that applies
to Canadians who tried to scam CERB. The feds are already reviewing past applications and considering penalties for fraudsters. You could report him using the Canada Revenue Agency’s leads program, which is essentially a snitch hotline, but I can understand why finking on a friend might not be that appealing. Given his obvious lack of ethical integrity, try appealing to his self-preservation instincts: tell him he could be charged for fraud under the Canadian criminal code. Hopefully that deters him from continuing his lawless lifestyle.