Dear Urban Diplomat: Do I have to follow this restaurant’s large-party rules?

I recently spent a week looking for a half-decent downtown restaurant that would reserve a table for 11. When I finally found a spot, which shall remain nameless, the staff recited a list of caveats: a minimum spend of $990, an automatic 20 per cent gratuity, a two per cent administration fee and hefty penalties if I cancelled with less than 48 hours’ notice. It was like they were punishing me for giving them my business. Are these conditions normal? Or can I push back? —Table Scraps, Flemingdon Park

Built-in tips and cancellation fees are standard practice for large parties, with good reason: big groups can be a pain for servers and no-show resos can wreak havoc on a restaurant’s bottom line. Beyond that, reservation conditions vary widely by location, party size and even date (booking a table during TIFF can involve more fine print than signing up for a timeshare). If you’re thinking of haggling over the admin fee or minimum spend by, say, threatening to take your business elsewhere, I’d say go for it. But be prepared to get shot down: restaurateurs know how hard it is to nab a table for 11—and they’re likely to call your bluff.

Dear Urban Diplomat, I take a taxi to and from my office in the Financial District during the winter. More than once, my drivers have completely ignored the new rules on King Street, cruising straight through intersections. I feel bad—I cycle during the summer and know how irked I’d be by a rogue cab if I were on my bike—but it gets me to work in record time. Am I just as bad as the cabbies if I don’t say something? —Lying King, Niagara

You’re not pressuring your drivers to flout the rules, and there’s no guarantee you could convince them to obey them either. Nor would you face the potential consequences: the cabbies and their companies would have to deal with the $110 ticket. But you’re not off the ethical hook. Standing (or sitting) idly by makes you complicit. If you feel guilty enough to ask the question, you already know that speaking up is the only way to clear your conscience.

Dear Urban Diplomat, Last weekend, on the Danforth ­subway, my train got delayed between stations. I was sitting next to an attractive woman who looked about my age, so I tried to chat with her to pass the time. She was reading a book, and I asked if it was any good. She said yes and went back to reading. When I followed up to ask what it was about, she went off on me, telling me I was making her uncomfortable and needed to leave her alone, which earned me some dirty looks from other commuters. I was trying to be friendly, not creepy. Was that so wrong? —Train Wreck, Greektown

When she made it clear she was more interested in her book than your banter, that was your cue to stand down. Her reaction may have been excessive, but try to see things from her perspective. Women are routinely bombarded with unwelcome male attention. And at a time when news of a new groping TV star or pervy politician breaks every few hours, if women feel empowered to speak up, I say more power to them. It’s not a crime to be amiable, but for god’s sake, read the room—or, in this case, the train.

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