Dear Urban Diplomat: My rich friends are using me to avoid the Vacant Home Tax

Dear Urban Diplomat, I’m friends with a wealthy couple who own a gorgeous Victorian in the east end, and they’ve presented me with an offer that’s too sweet to pass up. They plan to spend 2025 travelling the world and want me to house-sit until June. With this year’s reporting deadline for the Vacant Home Tax coming up, I think they’re using me to avoid the levy. The city needs the money, but living rent free is a dream. Should I swallow my ethics and accept? —Artful Lodger, Kennedy Park

Six months occupancy is the minimum for property owners who want to avoid the tax, so the timeline of their offer is indeed sus. But the point of the tax is to incentivize owners to increase the housing supply, and they’re not doing that unless you offer your current place up to someone who needs it. I’d suggest listing your place as a short-term sub-rental, then see if you can weasel your way into house-sitting for the whole year. Two birds, ethically killed.

Dear Urban Diplomat, There’s an elderly woman in my building who always asks for a hand crossing the street. I’m happy to do a good deed—but she’s so rude. Every time I help her, she berates me about how I’m moving too slowly or carrying her shopping bags wrong. I often see other neighbours on her arm, grimly enduring her verbal abuse. Last week, on a promising first date, the lady approached me and I waved her off. My date looked at me sideways and never texted me back. Am I a bad person? —Double Crossed, Flemingdon Park

No, but your date wasn’t wrong to think so. How we treat senior citizens is an indicator of our character. Your date’s would-be affection may have been worth five minutes of indignity with the resident curmudgeon, in a mercenary sense, but that’s for you to decide. As for the more general matter of indulging a rude neighbour: you shouldn’t have to ruin your day to make someone else’s. The next time she snipes, remind her that civility is a two-way street.

More Urban Diplomat

City

Dear Urban Diplomat: I’m dreading my roommate’s US election party

City

Dear Urban Diplomat: My cousin used AI to write my father’s eulogy

City

Dear Urban Diplomat: Speed-demon cyclists are taking over High Park

Dear Urban Diplomat, Google Alerts sent me an email about my own surprise wedding (yes, I have an alert for my name, for business purposes). And I was completely floored. My partner and I have talked about marriage as a distant possibility for years, but the expense, the churchiness, the eye-rolling banality of being capital-M married has always been a mutual deterrent. Or so I thought. Isn’t a house and two kids enough legal entanglement? How should I break it to my groom-not-to-be? —Unholy Matrimony, Wellington Place

No one should have to RSVP “no” to their own wedding. You need to make it clear to your partner that it’s unacceptable for him to cast you as a bit player in your own life. Then you need to figure out if you can forgive his colossal lapse in judgment. In the meantime, be thankful that your narcissism (or, if you insist, your business needs) saved you from a public anvil-dropping on your relationship.

Dear Urban Diplomat, Planning outings with my friends is more complicated than achieving consensus at the UN. No matter what location, activity or time I propose, someone has an issue. Skating on Grenadier Pond? Too cold. Bar-hopping on College? Too undergraduate. Buck-a-shuck? Someone doesn’t like seafood. Two p.m.? Too early. Nine p.m.? Too late. I feel like millennials have been coddled into thinking that every opinion and preference, no matter how slight, must be accommodated. How do I tell them that I’m their friend, not their social convener? —Party Trooper, Dufferin Grove

Organizing group hangs is a thankless job. I’d suggest letting your friends initiate the planning—they’re likely just lazy, not ungrateful—but I suspect that you’d never end up hanging out. My advice is to make the plan firm and specific before you present it. Leave no room for a veto. Pick a date. Book the table. Rent the skates. Text them the time and place. There’s a strong chance that their quibbling will conveniently turn into compliance.

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