O choose me for your Valentine!

Who sent the first Valentine in North America? The truth might surprise you, as the sender is associated very closely with early Canada.

By Serena Ypelaar

On February 14, 1779, British Lieutenant Colonel John Graves Simcoe, who would later become the founder of York (Toronto) and the first governor of Upper Canada, sent an impassioned valentine – to a Patriot’s daughter.

John Graves Simcoe’s signature. Photo: Wikimedia

Historically, Simcoe is an interestingly dual figure. You may have seen him in TURN: Washington’s Spies (the AMC series I can talk about for days if allowed) or at Fort York National Historic Site if you’re familiar with Toronto’s history.

Lieutenant Governor John Graves Simcoe, painted c. 1881.

In TURN, he’s wholeheartedly vilified based on his true-to-life role in oppressing American colonists and carrying out attacks such as the Massacre at Hancock’s Bridge (1778). But in southern Ontario, he’s venerated as the founder of York, earliest administrator of Upper Canada, and a staunch abolitionist. Simcoe passed the first Act Against Slavery in 1793 (only a year or so after accepting the post of Lieutenant Governor) and ensured that there were no slaves in Upper Canada by 1810 – 24 years before the rest of the British Empire finally abolished slavery in 1834.

The moment I assume the Government of Upper Canada under no modification will I assent to a law that discriminates by dishonest policy between natives of Africa, America, or Europe.

John Graves Simcoe to the Legislative Assembly

Before governing Upper Canada, Simcoe was stationed in Oyster Bay, New York during the American Revolution. He and another officer stayed at the home of notable Patriot Samuel Townsend and his family.

Simcoe, then almost 27, took a liking to Samuel’s 18-year-old daughter Sarah “Sally” Townsend, and it’s said that on Valentine’s Day 1779, he gave her a valentine letter consisting of a 52-line 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!

Love, Mighty God! Thou know’st full well
Where all thy Mother’s graces dwell,
Where they inhabit and combine
To fix thy power with spells divine;

Thou know’st what powerful magick lies
Within the round of Sarah’s eyes,
Or darted thence like lightning fires
And Heaven’s own joys around inspires;

Thou know’st my heart will always prove
The shrine of pure unchanging love!
Say; awful God! Since to thy throne
Two ways that lead are only known-

Excerpt from Simcoe’s valentine poem to Sarah Townsend

Thematically, the poem addresses the implications of loving an enemy – apparently such poetic romances truly aren’t just a thing of fiction.

Sarah is known to have had a brief flirtation with Simcoe during his time in Oyster Bay. Declaring his love for her, he asked her to choose him as her valentine, but their relationship was not to be. Simcoe ended up in Upper Canada after the Revolutionary War (1775-1783), and Sarah remained in Oyster Bay. She never married; the valentine was discovered among her possessions after her death in 1842.

It’s unknown whether Sarah returned Simcoe’s feelings.  The nature of their relationship is further complicated by the fact that Sarah is thought to have spied on Simcoe. Sarah’s older brother Robert was a key operative of the Culper Spy Ring, George Washington and Benjamin Tallmadge’s intelligence network (and the core focus in TURN). Under the codename Samuel Culper Jr., Robert Townsend fed secrets to the Ring to advance the Patriot cause.

Legend claims that Sarah overheard Simcoe speaking to Major John André about their plans to take West Point using leaked intelligence from notorious turncoat General Benedict Arnold. Robert’s subsequent tip to the Ring would result in André’s capture and hanging as a spy. Given that the Townsends were working against the British, the relationship between Sarah and Simcoe has a decidedly Romeo-and-Juliet air – the only question is whether Sarah loved him back.

Raynham Hall, the Townsend family home. Photo: Wikimedia

We don’t have any physical written evidence to reveal Sarah’s feelings, but a colonial-era windowpane of the Townsends’ home survives today. This windowpane contains a message scratched into the glass by a British officer to “the adorable Sally Sarah Townsend”. Was it Simcoe who scratched the message? It’s possible, given that he was living there, but not proven.

Where’s the valentine now? It’s preserved in the place where it was first given – Raynham Hall Museum, Oyster Bay. The Townsends’ home is now a historic museum focusing on Robert Townsend’s role as a Patriot spy, as well as the family’s history from the time Raynham Hall was built in 1740.

Amidst the hearts and chocolate, we don’t often stop to consider historic valentines. Valentine-giving is an age-old tradition that tells us a lot about love and the conventions of the time (and the weight and respect that love poetry once commanded!).

As far as Simcoe and Sarah’s story goes, the evidence of this particular love is one-sided; but was the romance one-sided too? We’ll likely never know.

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