The Toronto Book of Love

1. Ancient Peoples Embraced Diverse Forms of Love and Freedom

"A young woman, say they, is master of her own body, and by her natural right of liberty is free to do what she pleases."

Wendat autonomy. Centuries before Toronto's founding, the Wendat (Huron) people on Lake Ontario's shores practiced a remarkably free approach to love and relationships. Young men and women could sleep together without marriage, and multiple partners were accepted, with women holding ultimate control over their bodies and choices.

Cultural contrast. French soldier Louis-Armand de Lahontan, observing Wendat customs, noted their "tender friendship" and "simple goodwill," though he likely underestimated the depth of their passion. This contrasted sharply with European norms, where French missionaries actively sought to suppress premarital sex and divorce, even offering money to Wendat wives to prevent separations.

Enduring legacy. Despite colonial pressures and cultural genocide, the Wendat's oral histories and early European accounts reveal a society where love was expressed with freedom and respect for individual liberty. Their traditions, though challenged, highlight a foundational diversity in the region's romantic history, a stark contrast to later European impositions.

2. Early European Settlements Were Shaped by Personal Scandals and Strict Morals

"He wasn’t about to let an unsettling age difference or the feelings of his preteen bride stand in the way of his dreams for his Canadian colony."

Founding marriages. The early European presence in Toronto was deeply intertwined with personal relationships, often scandalous. Samuel de Champlain, "The Creator of New France," secured vital funding for the colony through a disturbing arranged marriage to a twelve-year-old girl. Later, Governor Frontenac, fleeing a tumultuous marriage and financial ruin in France, focused on expanding French influence, leading to the establishment of Fort Toronto.

Love and diplomacy. Fur traders like Jean Baptiste Rousseau often married Indigenous women, fostering crucial alliances and cultural exchange, a practice that blurred European and Indigenous customs. However, with the arrival of the British and Governor John Graves Simcoe, strict Anglican marriage laws were imposed, invalidating many existing unions and sparking decades of confusion and conflict over what constituted a "proper" marriage.

Honor and tragedy. Early York society, though small, was rife with drama. The fatal New Year's Duel of 1800 saw Attorney General John White killed over salacious accusations of infidelity against Elizabeth Small, highlighting the brutal consequences of gossip and the rigid code of honor. Charivaris, boisterous public shaming rituals for controversial marriages, further underscored the community's attempts to enforce social norms, sometimes with dangerous results.

3. Hidden Desires Faced Harsh Scrutiny in Conservative Colonial Society

"He would remain a bachelor to the end of his days, raising more than a few eyebrows in a province where homosexuality was not only illegal, but punishable by death according to the letter of the law."

The Wood scandal. Alexander Wood, a prominent Toronto merchant and magistrate, became the center of a notorious scandal in 1810. Accused of sexually inappropriate examinations of men under the guise of a rape investigation, he was publicly ridiculed as the "Inspector General of Private Accounts" and forced into exile. His land later became the heart of Toronto's LGBTQ+ community, making him a posthumous queer icon, though the true nature of his relationships remains a mystery due to societal prejudice.

Markland's downfall. Decades later, George Markland, a powerful Family Compact leader, faced a similar inquiry into his private life. Accused of "unmanly" and "feminine" behavior, his career was destroyed despite his denials. These incidents reveal the severe penalties—social ostracization, exile, and even the threat of death—faced by individuals whose sexuality deviated from rigid Victorian norms in "Toronto The Good."

Pervasive prejudice. The legal and social environment of early Toronto forced queer individuals to live and love in secrecy. Laws against sodomy, punishable by death, were rarely enforced but created a climate of fear. This systemic prejudice meant that much of Toronto's early queer history remains unrecorded, leaving figures like Wood and Markland as poignant, if ambiguous, symbols of hidden lives.

4. Love Endured and Inspired Amidst War and Political Rebellion

"If he was destined to take his last breath on that battlefield, FitzGibbon’s final act would be to take care of the woman he loved."

Wartime sacrifices. The War of 1812 and the 1837 Rebellion deeply impacted personal lives and relationships. Isaac Brock, a national hero, is immortalized in the romantic (though likely mythical) tale of his secret engagement to Sophia Shaw, a story that underscores the human cost and emotional stakes of conflict. Zebulon Pike, an American general, penned a poignant last love letter to his wife, Clara, before his death during the American invasion of York, highlighting the personal farewells made before battle.

Daring devotion. Captain James FitzGibbon, a celebrated hero of the War of 1812, took a daring three-day leave from the Siege of Fort Erie to marry Mary Haley, ensuring she would receive a pension if he died. This act of devotion, amidst the brutal realities of war, illustrates the profound commitment individuals made to their loved ones in uncertain times.

Rebel hearts. The 1837 Rebellion saw love intertwined with political conviction. Isabel Baxter Mackenzie stood by her husband, William Lyon Mackenzie, through political violence and exile, even turning her petticoats into cartridge bags. Samuel Lount, a rebel blacksmith, was executed for treason, but his wife, Elizabeth, bravely petitioned for his life and later published a scathing open letter, ensuring his memory as a martyr for Canadian freedom. Joseph Gould, a Quaker rebel, carved a "Rebellion Box" for his fiancée, Mary James, inscribed with a promise of reunion, symbolizing hope amidst imprisonment and the fight for democracy.

5. The Fight for Freedom from Slavery Forged New Lives and Communities

"The Blackburns might have been living hundreds of kilometres from the South, but they still weren’t safe — not even in a free territory like Michigan."

Escape to freedom. Thornton and Ruthie Blackburn, born into slavery in Kentucky, risked everything for love and liberty. Their daring escape across the Ohio River, through Indiana and Ohio, culminated in Detroit, where they briefly found freedom before being recaptured. The subsequent "Blackburn Riots" in Detroit, sparked by community efforts to prevent their return to slavery, forced many Black residents to flee to Canada.

A Canadian haven. Despite being arrested upon arrival in Canada, the Blackburns' case solidified Upper Canada's reputation as a safe haven for those escaping American slavery. With the support of abolitionists, they were released, finally finding true freedom in Toronto. They settled in the city, changing Ruthie's name to Lucie, and became pillars of the burgeoning Black community.

Community builders. The Blackburns' entrepreneurial spirit led them to establish "The City," Toronto's first horse-drawn taxi, which made them wealthy. They used their resources to buy property in "The Ward," renting homes at discount rates to other newcomers from the Underground Railroad. Their activism extended to anti-slavery societies and supporting the Buxton settlement, transforming Toronto into a vital hub in the fight against slavery and laying foundations for its multicultural future.

6. Rapid Urban Growth Exposed Social Hypocrisy and Marginalization

"It was powerful landlords like Boulton who stood to gain the most from sex work. They charged brothel keepers like Daniel Bloxsom inflated rents and rarely faced any consequences."

Toronto's hidden vice. As Toronto rapidly grew in the mid-1800s, its image as "Toronto The Good" masked a thriving underworld of vice. Brothels, often disguised as legitimate businesses like oyster shops, operated across the city, catering to a bustling population. This industry, though illegal, was often tolerated by powerful figures, including Mayor William Henry Boulton, who owned properties used as brothels.

Vulnerable women. The Great Famine in Ireland led to a massive influx of Irish immigrants to Toronto, many of whom, facing desperate poverty and discrimination (especially Catholics from the Orange Order-dominated city), were forced into sex work. These women, often young and marginalized, bore the brunt of legal prosecution, facing fines or hard labor, while their male clients and powerful landlords like Boulton largely escaped consequence.

Moral policing. The city's moralizing leaders, particularly the Orange Order, sought to enforce strict social codes. While they cracked down on public drunkenness and "immorality," their actions often targeted the most vulnerable, highlighting a deep hypocrisy. The "Circus Riot" of 1855, sparked by a brawl at a brothel, exposed the police force's complicity and led to reforms, but the underlying social inequalities and prejudices persisted for decades.

7. Artists Challenged Conventions, Forging Identity and Unconventional Partnerships

"I always wished I were a boy," she admitted. "And so, in Jalna it wasn’t the heroine she saw as a reflection of herself, it was the swashbuckling male hero."

Literary secrets. Mazo de la Roche, a globally celebrated Canadian author, lived a life intertwined with her cousin Caroline Clement in what was likely a "Boston Marriage." De la Roche's "Jalna" series, which brought her international fame, subtly explored themes of gender and sexuality, with characters like Renny and Finch serving as her "alter egos." She fiercely guarded her privacy, blurring fact and fiction in her autobiography and even burning her personal papers, leaving the true nature of her relationship with Clement a mystery.

Sculpting new paths. Frances Loring and Florence Wyle, "The Clay Ladies," were pioneering sculptors who brought bohemian life to conservative Toronto. Their shared studio, "The Church," became a hub for artists and intellectuals, challenging the city's rigid social norms. Despite facing prejudice as female artists and likely as a queer couple, they made significant contributions to Canadian art, culminating in Loring's iconic "Lion" monument on the QEW, a testament to their artistic partnership and resilience.

Indigenous voice. Pauline Johnson, a Kanien’keha:ka poet, used her dual heritage and theatrical performances to challenge colonial perspectives. Her poem "A Cry from an Indian Wife" offered a poignant Indigenous woman's view of war, forcing Victorian audiences to confront the pain of colonization. Her work, alongside figures like de la Roche, Loring, and Wyle, demonstrated how art and unconventional lives could push boundaries and reshape cultural understanding in a rapidly changing Toronto.

8. Great Wars Brought Both Heroic Romances and Heartbreaking Separations

"It is wonderful to think of those glorious days coming in our lives when night and day I can hold you in my arms and love, love, love you!"

Wartime celebrity. The First World War transformed lives and loves. Billy Bishop, a charming and rebellious young man, used his wartime heroism as a flying ace to overcome social barriers and marry Margaret Burden, an heiress of the powerful Eaton family. Their romance, fueled by his fame and her unwavering love, became a national sensation, though his infidelity and the psychological toll of war would later complicate their marriage.

Tragic misunderstandings. Tom Longboat, the world's greatest marathon runner, enlisted in the First World War, serving as a vital dispatch runner on the Western Front. Despite surviving brutal battles like Vimy Ridge and Passchendaele, he returned to Toronto to a devastating personal loss: due to repeated administrative errors, his wife, Lauretta Maracle, had been informed of his death and remarried. This tragic misunderstanding ended their marriage, highlighting the profound human cost of wartime communication failures.

Disdain for Toronto. Ernest Hemingway, a young journalist for the Toronto Star, found Toronto's conservative, Prohibition-era atmosphere stifling. His brief, unhappy time in the city, marked by the birth of his son and clashes with his editor, fueled his disdain for "Toronto The Good." He and his wife, Hadley, secretly moved out of their apartment piece by piece, eager to return to the bohemian freedom of Paris, where his literary career would flourish, but their marriage would eventually end.

9. Love Persevered Through Unimaginable Prejudice and Survival

"I made an agreement in those moments when the napalm scorched my clothing and … my skin and then the fat and muscle and other tissue, that because I would now and forever be seen as ‘different,’ I was unfit to be loved."

"Incorrigible" love. Velma Demerson, an 18-year-old white woman, was arrested and imprisoned in Toronto's Andrew Mercer Reformatory in 1939 for loving and being pregnant by Harry Yip, a Chinese Canadian man. Convicted of being "incorrigible" under the Female Refuges Act, she endured horrific medical experiments and solitary confinement, a stark example of state-sanctioned racism and control over women's bodies and choices. Her fight for justice continued for decades, culminating in a provincial apology in 2003.

Auschwitz miracle. Miriam Rosenthal, a young Orthodox Jewish woman, married Bela Rosenthal in Hungary in 1944 amidst the Holocaust. Separated weeks later, Miriam was sent to Auschwitz, where she miraculously hid her pregnancy. Transferred to Kaufering I, she joined six other pregnant women in the "Schwanger Kommando," enduring unimaginable conditions. Against all odds, she gave birth to her son, Leslie, in a concentration camp, a testament to the resilience of life and love in the face of genocide.

Reunion and new life. Both Miriam and Bela survived the war, finding each other and their miracle baby, Leslie. They eventually settled in Toronto, opening Miriam's Judaica, a store that became a symbol of their enduring love and resilience. Their story, and Demerson's, highlight the profound strength of individuals who found love and built families despite facing the most extreme forms of prejudice and suffering.

10. The Swinging Sixties Ushered in New Eras of Love and Self-Discovery

"Tell her that I’m happy," she sang. "Be sure and tell her this: tell her that I’m gay. Tell her I wouldn’t have it any other way …"

Yorkville's folk revolution. Toronto's conservative facade began to crack in the 1960s, particularly in Yorkville, which became a vibrant hub for folk music and counterculture. Joni Mitchell, a young musician, arrived pregnant and unmarried, facing societal judgment and the heartbreaking decision to give up her daughter for adoption. Her experiences in Yorkville, and her eventual move to Laurel Canyon, fueled her iconic music, including "Little Green," a poignant song about her lost child.

Trailblazing soul. Jackie Shane, a Black transgender soul singer from Nashville, found her home and freedom in Toronto's Yonge Street Strip in the 1960s. Performing in sequined pantsuits and openly discussing her sexuality, Shane defied gender norms and racial prejudice, drawing diverse crowds to the Saphire Tavern. Her live album, recorded in 1967, became a powerful testament to her authenticity and resilience, inspiring countless queer individuals in a city still grappling with homophobia.

Hollywood scandal in Toronto. Elizabeth Taylor and Richard Burton's tempestuous affair and subsequent marriage played out dramatically in Toronto in 1964, where Burton was starring in "Hamlet." Their stay at the King Edward Hotel, while scandalous to moralizers, was defended by the Toronto Star, signaling changing attitudes towards celebrity and divorce. Margaret Trudeau, wife of the Prime Minister, later found her own path to self-discovery, famously partying with The Rolling Stones at the El Mocambo, challenging the rigid expectations of her role and embracing a new, independent life.

11. The Battle for Equal Love Transformed Toronto's Legal and Social Landscape

"From our first consciousness we were taught we could never have that, that we’re bad people not allowed to dream that dream."

The bathhouse raids. Despite gradual decriminalization of homosexual acts in Canada in 1969, Toronto's LGBTQ+ community continued to face severe oppression. The 1981 "Operation Soap" bathhouse raids, which saw over 300 men arrested, sparked massive protests and galvanized the city's Pride movement. This event, a stark reminder of ongoing homophobia, became a pivotal moment in the fight for gay rights.

Pioneering advocacy. Michael Stark and Michael Leshner, who met shortly after the raids, became leaders in this struggle. Leshner, a lawyer, launched landmark lawsuits against the Ontario government, demanding equal pension rights for same-sex couples and challenging discriminatory employment practices. Their personal commitment to their relationship fueled their public advocacy, pushing for legal recognition and social acceptance for queer love.

Marriage equality. After decades of activism, the Metropolitan Community Church in Toronto, led by Reverend Brent Hawkes, challenged discriminatory marriage laws by performing same-sex weddings in 2001. This act of defiance, supported by couples like the Michaels, led to a legal battle that culminated in the Ontario Court of Appeal declaring same-sex marriage legal in 2003. The Michaels, married in a courthouse cloakroom, became symbols of this historic victory, celebrating their union in a Pride parade that transformed from protest to joyous celebration.

12. Toronto's Enduring History is Woven with Countless Acts of Love and Connection

"Imagine how it would create a new view of this city, not of cold and concrete, but as a place of connection, softness, and tiny moments of love."

A city of kisses. The Toronto Kiss Map, a modern interactive project, beautifully illustrates that Toronto's history is not just of buildings and events, but of countless intimate moments. From ground-shaking first kisses on street corners to tender farewells at Union Station, these personal stories of love, lust, and heartbreak form a "psychogeography of love" that spans centuries.

Evolving romance. The city has witnessed a profound evolution in attitudes towards love and sexuality. From the Wendat's ancient freedoms to Simcoe's rigid Anglican marriage laws, and from the scandals of early York to the decriminalization of homosexuality and the legalization of same-sex marriage, Toronto's romantic landscape has continuously adapted. Modern trends like dating apps, polyamory, and a greater emphasis on consent continue this ongoing transformation.

Collective endeavor. Toronto, a bustling metropolis, is built not only of physical infrastructure but also of the ephemeral yet powerful forces of human connection. Every held hand, every love letter, and every kiss contributes to the city's romantic architecture, making it a vibrant monument to the diverse loves and lusts of all who have called it home, past and present.

Last updated: January 3, 2026