Toronto's association with Valentine's Day stretches back nearly two hundred and fifty years, to a time before the city was even founded. In fact, it goes back to the very first Valentine ever sent in North America.
The founder of the city, John Graves Simcoe, was a dashing young officer back then, fighting on the British side of the American Revolution. He was stationed outside New York City, billeted with an American family on Long Island. It was there that he fell in love with the family's daughter: Sally Sarah Townsend.