WASHINGTON—A businesswoman whose lifestyle brand is struggling with liberals. A liberal-multilateralist prime minister who needs an in with a conservative-nationalist president.

Diplomacy is rooted in interests. And Ivanka Trump and Justin Trudeau both have an interest in hanging out with each other.

“It is just so Game of Thrones‎,” said John Higginbotham, a former Canadian diplomat in Washington, referring to the television show in which warring family dynasties strike strategic alliances in ruthless pursuit of power.

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