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My wife and I recently bought a cottage. It’s a charming two-bedroom with a bunkie near Orillia. Unfortunately, my university buddies, with whom I’m still close, have decided it’s their cottage, too. One even circulated a Google doc so everyone could lay claim to the bunkie this summer. How do I break the news to my friends without offending them?
—Former Frat Boy, Moore Park
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Dear Urban Diplomat: How do I tell my friends that they can’t come to my cottage every weekend?
Dear Urban Diplomat: How do I stop guys from pestering me when I’m jogging?
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I’m a 31-year-old woman, and I jog every day in and around Little Portugal. The older men in the neighbourhood feel compelled to cheer, catcall and sometimes run alongside me for short distances. It’s harmless but incredibly annoying. I’d like to arm myself with a comeback that will make it stop. What do you suggest?
—Fuming on Runs, The Annex
Dear Urban Diplomat: I found $100 in the back of a cab. What should I do with it?
I got into a cab a few days ago outside First Canadian Place and found a $100 bill on the floor. I quickly stuffed it into my pocket, but I’ve been feeling guilty ever since. I’m a manager at PwC, and I definitely don’t need the money as much as my cabbie probably does. I ended up spending it on overpriced martinis that night, making me an even bigger heel. What would you have done?
—Taxi Cab Confessor, Harbourfront
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Dear Wedding Diplomat: Too many guests RSVP’d for our destination wedding. What can we do?
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My fiancé and I are having a destination wedding in Cancún in April. We reserved a villa for 40 guests but sent out 60 invites, assuming at least 20 people—acquaintances, second cousins and the like—would decline. We were shocked when we counted the RSVPs and realized we had 66 people, including partners and kids. The rest of the resort is booked. Should we tell them about the room shortage and hope they back out?
—RSVPeeved, Roncesvalles
Dear Urban Diplomat: How do I tell my best friend that his on-court tantrums won’t fly at my tennis club?
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I’m the head of my tennis club’s membership committee, and my best friend is angling to get in. Unfortunately, his tantrums make ’80s-era John McEnroe seem like a cooing turtledove by comparison. If I allow him in, I risk being ostracized by the club. If I turn him down, I fear it may end of our friendship. What should I do?
—Enter at My Own Risk, High Park
Dear Urban Diplomat: My neighbour roots through my recycling bin. Can I ask her to stop?
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My neighbour is a total eco-Nazi. She leads an enviro group and hosts a regular Skype chat on carbon footprint reduction strategies. The other day, I put my blue bin out for pickup, then watched through the blinds as she wandered over, plucked out my hair dryer and some vinyl records and placed them on our porch. My husband had to restrain me from flinging open the door and throttling her. I want to say something, but how?
—Recycling Rage, Cabbagetown
Dear Urban Diplomat: How do we tell our otherwise perfect babysitter that drinking on the job isn’t cool?
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My wife and I discovered the parenting Holy Grail: a babysitter who’s punctual, affordable and amazing with our kids. Last time she sat, we told her to help herself to anything in the fridge. When we got home, she was a bit chattier than usual. We paid her and she drove home. Then we discovered a bottle of wine sitting empty on the counter—it had been three quarters full when we left. Was she drinking while playing with the kids? Was she driving drunk? We want to keep using her, but we don’t know how to broach the drinking issue. Help!
—Parental Guidance Needed, High Park
Dear Urban Diplomat: Can I stop rude drivers from budging at a lane-closure queue?
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The left lane is closed about halfway along the off-ramp from the Bayview extension to River Street. Yet every morning, despite the lane closure signs, one in 10 drivers speeds past the queue and squeezes in at the bottleneck, making everyone else’s commute even more excruciating. One morning, I’d had enough, so I positioned my car over the dotted line, blocking the left lane. Some guy in a black BMW drove up behind me and laid on the horn. I held my ground. I think everyone else appreciated it—in fact, another driver mimicked my move. I was right, right?
—Vigilante in a Tercel, Davisville
Dear Urban Diplomat: Am I obligated to provide a gluten-free option at my kid’s birthday party?
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Last week we sent out e-vites for our son’s 10th birthday. The RSVPs started coming back, and in two cases, parents wrote “gluten-free preferred” in the space for allergies and dietary restrictions. What the heck is that? I’m not asking for preferences—I’m asking if their kid will keel over if he catches a whiff of chocolate icing or offend Allah by consuming non-Halal pepperoni. I’m disinclined to accommodate these requests, but my husband thinks we should, to avoid any social awkwardness. Am I out of line here, or are they?
—Let Them Eat Cake, Streetsville
Dear Urban Diplomat: Are bidding wars on rental condos socially acceptable?
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I went to a viewing of a rental condo recently—a great place with an office, a fireplace, a gym downstairs and cheap rent ($1,200). It seemed perfect until the seller said he’d be accepting blind bids. I know bidding wars are common in home sales, but this was a rental! I felt cheated, and said so before storming out. I’m sure I was right, but my friends think I’m a nutbar. Can you settle it?
—Bidding Warrior, Dupont and Spadina
Dear Urban Diplomat: I find the skateboarder memorial outside my building upsetting. What can I do?
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A skateboarder was killed by a cab outside my building, and six months later, the sidewalk memorial is still there. I realize that this is not the politically correct thing to say, and I’m not a heartless troll, but I don’t want to be reminded of the awful event every day. It’s public space, not a graveyard. Short of dismantling it, what are my options?
—Death to Death Memorials, King and Jarvis















