Dear Urban Diplomat: I just found out that my roommate is pro-Putin

Dear Urban Diplomat,
I recently found out that my roommate, who’s originally from Russia, supports Putin. Up until then, we got along great, but I can’t get past this. His position seems unjustifiable, especially for someone living beyond the reach of the Russian propaganda machine, yet he’s steadfast in his devotion. I’m seriously considering moving out. What should I do?
—Seeing Red, Waterfront

UD: In any domestic situation, each party needs to maintain a certain level of tolerance, putting up with all sorts of unseemly behaviour, like laundry left in the dryer and dirty dishes in the sink. That type of stuff is inevitable, and a little give and take is necessary to keep the peace. But, when your roomie supports a dictatorial war criminal, the relationship is beyond repair. Start searching for alternate lodging, citing irreconcilable differences, and put a moratorium on political talk in the household. Don’t bother trying to change your roommate’s views—if that fails, I fear it’s too late.

Dear Urban Diplomat,
I live on a street with permit parking, and it’s never been difficult to find a spot, until recently. One of my neighbours started a big reno, and the construction workers have been blocking off half the street with pylons, reserving spaces for their trucks. Now I can never find parking. I complained to their contractor, but he basically told me to piss off. Any ideas?
—Tight Spot, Dovercourt Park

UD: Talk to the homeowners directly, and ask them to take up the matter with their contractor—he answers to them, not you. They might be able to reduce the number of hours the spots are blocked off or even save you a space. Otherwise, call parking enforcement at 416-808-6600. Unless those trucks have a permit, they’re parked illegally. And nothing says “piss off” right back better than a bunch of yellow flags on the dashboard.

Dear Urban Diplomat,
I’ve worked at the same recruiting company for the past decade. Recently, my boss hired his daughter, who’s fresh out of university, with a BA in sociology and a bit too much self-confidence. She’s just a couple of months into her tenure and already oversees some of our most lucrative accounts, with the commissions to match. It’s annoying for everyone, but I’m not sure my boss is aware of the effect it’s having on team morale. How do I broach this without sabotaging my own career?
—Not the Boss’s Daughter, Midtown

UD: Sadly, there’s no law in Ontario against nepotism. Challenging your boss’s decision and, worse, questioning his daughter’s worth is career suicide. Plus, you’re not going to change his opinion—his assessment of her skills will always be distorted by familial love. My advice is to sit tight and wait things out; if she chokes, her dad will have no choice but to rethink the distribution of accounts; if she excels and blocks opportunities for the rest of you, polish that resumé.

Dear Urban Diplomat,
I recently had coffee with an old high school friend who just moved to Toronto. It was fun catching up, but I never really expected to hear from them again. Well, in the few weeks since, they’ve been messaging me constantly, suggesting we hang out. It’s like they think we’re best friends. I’ve turned them down on a few occasions, but they don’t seem to be taking a hint. It’s maddening to keep seeing their name pop up in my phone. Thoughts?
—Friend-Zoned, Roncesvalles

UD: You did have fun with them the first time. Before you cast this person into friend purgatory, try hanging out with them a few more times. But set boundaries—keep it to once a month, in a setting where you feel comfortable. That should limit the number of texts you receive. After that, if you really can’t imagine slotting this person into your social calendar, see if you’ve got a friend with whom they might have something in common and arrange for them to meet. And just like that, you’re a networking genius.