Toronto

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Toronto just wants to be liked, although it would probably settle for being notorious. It's tough being the largest city in the smallest member of the industrialised world; nobody really cares that much. Even other Canadians can't really be bothered to despise Toronto, they merely mildly resent it. Actually the only people who really like Toronto are the people from Detroit, for whom Toronto is a cheaper, closer and cleaner version of New York. Granted it's not as exciting, but at least it's safe to take the kids; after all, they're better-armed than the muggers are.
Even worse, except for the people in Detroit nobody else has ever heard of Toronto! Most people have heard of Canada, if only because Canadians are always so very careful to explain that they're not Americans, but asking them to keep track of cities? That's a bit much, isn't it? It's not like Toronto is pretty or memorable; contrast Vancouver or Montreal.
At least you can always count on being able to find somewhere interesting to go for dinner.

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