Dear Urban Diplomat, My roommate wants to host a house party on the night of the American election, and I’m dreading it. Forgive me, but it’s hard to make merry when the future of democracy is on the line. She already bought streamers and printed off memes to hang around the apartment. She also plans to fly the stars and stripes across our balcony, which I’m sure will freak out the neighbours. We’re not even American! Am I a bad roomie if I veto this sad event? —Party Politics, CityPlace
Sharing a space is always a negotiation, no matter how simpatico the occupants. But, before you begin debating the merits of this party with your housemate, consider a few things: like it or not, what happens in the States affects the entire planet. If things go south on November 5, there’s camaraderie and catharsis in a bit of collective grief. Now imagine your preferred candidate wins. Wouldn’t it be nice to celebrate the momentous victory en masse?
Dear Urban Diplomat, Ever since we met in university, my friends and I have picked one week a year to go on a group trip. Most of us are pretty chill about splitting bills, but one friend now insists on tracking our expenses in an app—right down to the coffees and Ubers. We just got back from a fantastic vacation in Mexico, and every few hours, he keeps sending alerts, imploring us to declare our purchases like some officious CRA auditor. I’m still working off my hangover. The last thing I want to do is rifle through receipts. What’s the move here? —Penny Wise, Fashion District
Unless your friend actually is an officious CRA auditor, he probably doesn’t enjoy tallying up receipts either. Examine the feelings behind his insistence. Maybe he doesn’t make as much money as the rest of you and feels the bite of vacation extravagance. Maybe he doesn’t drink as much and resents splitting the bill evenly for cocktails or bottomless mimosas. If it’s the penny-pinching that bothers you, for the next trip, you could set a minimum dollar amount—say $20—for logged expenses. But, if he refuses and wants to continue hounding you all, you have my permission to delete the app forever.
Dear Urban Diplomat, Over the summer, my teenage son fell in love with cycling—to the point where he’s saying he won’t get a driver’s licence. I support all the health and climate benefits, but now he’s gearing up to ride all winter. He bought new tires with heavy treads and a high-vis vest. Toronto’s streets seem more dangerous than ever, and I’m concerned about him riding around when the city turns into a hellscape of ice and slush. He’s a responsible kid in every other way. How can I help him see the risks? —Road Wary, South Hill
It sounds like your son already understands the risks. I can’t recall ever seeing a teenager proudly rocking a high-vis vest. But I will say this: while 2024 has not been a banner year for Vision Zero, Toronto’s cycling network is more robust than ever. Besides, winter riding can humble you fast. One look at that grey curbside sludge may send him running for his Presto card.
Dear Urban Diplomat, My husband and I saved up a down payment for a condo, but given the oversupplied market, he’s now eyeing a semi-detached fixer-upper with a backyard instead. He says he’s watched enough YouTube videos to manage a basic renovation, but I’ve never seen him so much as lift a hammer. I refuse to go through years of reno hell in a house I never loved in the first place. Who’s right? —Reno 911, Leslieville
A DIY reno can be empowering, but only for the truly determined. Try testing his resolve (and proficiency) by finding something that needs fixing in your current unit or some friends who could use a hand. If his competence claims don’t translate into actual skill—or will—you’ll have persuasive ammo for your argument.
NEVER MISS A TORONTO LIFE STORY
Sign up for This City, our free newsletter about everything that matters right now in Toronto politics, sports, business, culture, society and more.