A Brief History of Toronto Valentines - Dundurn
Feb 09, 2021

A Brief History of Toronto Valentines

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.

It was to her that he dedicated the continent's first Valentine. The holiday's roots laid in the days of ancient Rome, but in more recent centuries, it had been taking on romantic connotations. Simcoe embraced them wholeheartedly. To celebrate Valentine's Day in 1779, he wrote Townsend a poem — "Fairest maid where all is fair / Beauty's pride and Nature's care / To you my heart I must resign / O choose me for your Valentine!" — and attached a sketch of two hearts inscribed with their initials and joined together by Cupid's arrow.

Little did he know that he had chosen the wrong woman for his affections. The Townsend family were hiding a secret: they were die-hard revolutionaries. Sally herself is suspected to have been a member of a rebel spy ring, perhaps even to have been spying on Simcoe himself. She rejected his attention and his heart was broken. When he founded Toronto two decades later, it was with a deep-seated suspicion of all things American, as well as the democratic ideals for which his crush seems to have been willing to betray him.

As Toronto grew from the muddy frontier town of Simcoe's days into a booming Victorian metropolis, Valentine traditions boomed along with it. By the middle of the 1800s, the Globe was providing annual dispatches from the post office on the fourteenth of February. "The Post Office was crowded with the fair sex all day;" the newspaper reported on Valentine's Day in 1862, "and the smiles on their faces showed their swains had generally done the proper thing."

By then, the holiday had become big business. Thousands of Valentine's Day cards passed through the post office in a single year, some costing as much as five dollars — a truly impressive sum back then. Some weren't even sent with romance in mind: a few pranksters were known to take advantage of cash-on-delivery policies to send expensive cards as practical jokes.

During that period, the Globe invariably reported the holiday was going out of fashion, declining in popularity with every passing year. But, of course, their dire predictions never did come true. When a new century dawned, Valentine's Day was still being celebrated with gusto. The Eaton's department store, for instance, rolled out elaborate displays in an attempt to convince its customers to spend big on romance every year. By the end of the roaring 1920s, the number of cards handled by postal workers every year had rocketed to 150,000.

It was during that era that Toronto's most intriguing Valentine mystery began.

It all started in 1928, when Meryl Dunsmore was sixteen years old. She was a student at Central Commerce (now Central Toronto Academy) when she received a Valentine's Day card from a secret admirer. The next year, she got another. And another one the year after that.

It was the beginning of a tradition that lasted for decades. Even when Dunsmore grew up and got married, the cards kept coming. They were always anonymous, and no matter how hard she tried, she could never figure out who was sending them. As she grew older, they began to arrive from locations all over the world: Paris, Tokyo, Sweden, New Zealand, Barbados, Morocco, Norway... She moved six times, but they always found her.

She was seventy-six years old when she died in 1988, having never uncovered the identity of her faithful correspondent. But there was one last Valentine to come. Five minutes before Meryl Dunsmore's funeral began, a final gift arrived: a basket of yellow and green flowers accompanied by a card, one last message from the secret admirer who had wooed her over all those years. The message read simply: "Rest in peace, my Valentine."