Dear Urban Diplomat: what do I have to do to get my neighbour to stop being such a butthead?

Dear Urban Diplomat,
I live and work just steps from Pape and Danforth. One of the business owners smokes on his stoop near the library, which is irksome enough. Even worse is that he discards the butts on the sidewalk. This is not a smoker versus non-smoker issue—it’s about littering. The sidewalk is not his personal ashtray. How do I convey as much without sounding like a total buttinsky?

—Butting Heads With a Butthead, Danforth

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In order for bylaw enforcement officers to levy a $365 littering fine, they’d need to catch the offender in the act, which is unlikely—last year, the city didn’t dole out a single littering fine. It’s ­possible they’d fine him based on your eye­witness account in court (an iPhone recording alone isn’t enough), but that strikes me as an extravagant use of the court’s time, and yours. Before it gets to that, try talking to the guy. Get snippy and he’s liable to ash on your shoestrings, so ask politely if he might avail himself of the nearest ashtray. If there isn’t one nearby, call 311 and request one, but don’t hold your breath: the review process can take up to a year.

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