Loves and Losses That Shaped Edgar Allan Poe’s Mystique

Max Erkiletian

July 12, 2025

Once a year, in the misty hours before the dark of night gave way to the light of day, a masked figure draped in black passes among the tombstones of Westminster Burial Ground in Baltimore, Maryland. 

Moving at the pace of a silent dirge, the mysterious form pauses at the grave of Edgar Allan Poe. Before it leaves, the figure places a half bottle of cognac and three red roses at Poe’s final resting place. 

According to The Edgar Allen Poe Society of Baltimore, the “Poe Toaster” commenced this practice sometime around 1949. Since then, he has repeated this act of devotion on the anniversary of Poe’s birth, January 19, for fifty years. 

The simple tribute became widely known to Poe enthusiasts. In later years, crowds would gather just outside the cemetery waiting for the “Poe Toaster” to appear.

Even with such attention, no one ever tried to unmask the Toaster. His identity is unknown to this day. We do know that the Toaster was male, because on the fiftieth anniversary of the ritual, a note accompanying the brandy and flowers stated that the Toaster had died. His sons carried on the tradition in later years.   

The Toaster’s dedication and the many Poe devotees worldwide are a testament to the writer’s talent and emotional reach.

“Let my heart be still a moment and this mystery explore” The Raven

How Readers View Edgar Allan Poe

The Poe Toaster is perhaps the last layer of the multi-layered Poe mystique. However, it is also part of the spiritual fiber that binds readers to the writer.

According to Lapham’s Quarterly, many of Poe’s contemporaries characterized him as an engaging conversationalist exhibiting charm and wit. As a literary critic, he was often funny and satirical. Some even described him as athletic. 

However, it is Poe’s ear for the melody of melancholy that reaches across time to touch the same emotions in us all.

Edgar Allan Poe’s Literary Appeal

Poe’s most enduring works are hauntingly atmospheric, set in shadowy landscapes or Gothic mansions. His poems, short stories, and one novel employ dark descriptive narratives. Additionally, his sentence structure varies to create mood and tension. Poe’s short stories The Tell-Tale Heart and The Cask of Amontillado are examples of his prose style. In poetry, The Raven and A Dream Within A Dream showcase his use of language to create atmosphere and mood.

Part of Poe’s ongoing popularity is due to the relatability of his works. Despite the differences in customs, social norms, and technology between Poe’s time and ours, his poetry and stories remain as powerful and moving today as they were in his time. That is because he holds nothing back. Poe’s characters struggle with the same inner demons and loss that many of his readers face.

In addition to writing that probes the human soul, Poe is responsible for creating a genre of fiction that draws on the human intellect. He created the detective story within the mystery genre. 

Your idea of a good time may be to cozy up with an Agatha Christie novel or watch Law and Order. In either case, you are experiencing the lineage of Poe. His C. Auguste Dupin was the first fictional detective hero. Even Sir Arthur Conan Doyle gave a nod to Poe’s character in the Sherlock Holmes story, A Study in Scarlet

Poe certainly mined his abundant imagination for characters and storylines. But it was his experiences that shaped his narratives. Many of those experiences dealt with love and loss.

Poe Lost His Parents Early in Life

Born in Boston, Massachusetts, to actor parents, Poe’s losses began early.

His father abandoned the family in 1811. Poe was two at the time. Shortly thereafter, his mother, Elizabeth, made her way to Richmond as part of a theater troupe. However, by December, she had succumbed to tuberculosis.

Frances Allan—a friend of his mother—and her husband, John, took Poe in. Their last name accounts for Poe’s middle name. His older brother, William, was raised by relatives in Baltimore, and his sister, Rosalie, was fostered by William and Jane Scott Mackenzie of Richmond.

line drawing of Edgar Allan Poe
Line drawing of Edgar Allan Poe

Poe Lost More Loved Ones While Still In School

At age 14, Poe developed a crush on a schoolmate’s mother, Jane Stith Stanard. The next year, she died. As a result, Poe visited her grave regularly. 

Five years later, Frances Allan died. Poe was devoted to her for taking him in when he was orphaned. Unfortunately, he was in the army at the time of her death and was not able to get back to Richmond until the day after her funeral.

According to the Poe Museum, William Henry Leonard Poe, the writer’s older brother, died two years later, at the age of 24, in 1831. Henry, as he liked to be called, was also a writer. In addition, the brothers shared a fondness for drink. Depending on which account you want to believe, alcohol, tuberculosis, cholera, or a combination of all three caused his death. Whatever killed William, his death was another tragic loss for his brother.

Edgar Allan Poe’s First Love: Sarah Elmira Royster Shelton

The depth of Poe’s romantic relationships may be attributable to the loss of family. By extension, it could be related to the loss of two mother figures—Allan and Stanard. Then again, he may have been one of those romantic types who was in love with love. 

No matter the cause of Poe’s romantic attachments, they were intense. Many led to marital engagements.

His first engagement was to a childhood sweetheart, Sarah Elmira Royster Shelton. As neighbors in Richmond, they were smitten but drifted apart after he entered the University of Virginia. 

Ultimately, each married someone else. Subsequently, both were widowed. They renewed their relationship shortly before his death, and there were reports that they planned to marry.

Broken heart with blood symbolizing Edgar Allan Poe's broken engagement

Edgar Allan Poe and Sarah Helen Whitman's Broken Engagement

A year before reestablishing his relationship with Shelton, Poe was engaged to poet and essayist Sarah Helen Whitman, according to The Providence Athenaeum
She had declined his first proposal on the grounds that she was too old for him. Born six years to the day before Poe, Whitman wrote her suitor that:

I can only say to you that had I youth and health and beauty, I would live for you and die with you. Now, were I to allow myself to love you, I could only enjoy a bright brief hour of rapture and die.

However, she broke off their engagement after determining that Poe couldn’t keep his pledge to stop drinking.

Portrait of Edgar Allan Poe's wife, Virginia Eliza Clemm Poe
Portrait of Edgar Allan Poe's wife,
Virginia Eliza Clemm Poe

Edgar Allan Poe’s Young Wife: Virginia Eliza Clemm Poe

One woman, who seems to have never criticized Poe’s drinking—or anything else—was his cousin, Virginia. Perhaps she accepted Poe’s faults because of her youth. She was 13 when they married. Poe was 27. 

Some historians have speculated that their relationship was non-sexual. However, there is no doubt that it was based on a deep and durable love.

Writing to his friend George W. Eveleth a year after her death, Poe described Virginia as “a wife, whom I loved as no man ever loved before...” according to the National Park Service

Virginia died of tuberculosis on January 30, 1847, at age 24. That is the same age as his mother and brother. In addition, his mother also died of tuberculosis, while the same disease caused or played a part in his brother's demise. 

The poem Annabel Lee, published two days after Poe’s death, is thought to have been written out of grief over Virginia’s passing. 

Poe’s link to Virginia remained for the rest of his life. This was evident in his relationship with his mother-in-law, who was also his aunt. 

Virginia’s mother, Mrs. Clemm, had moved to New York to live with the couple. She stayed even after her daughter’s death. Their affection was evident in Poe’s pet name for Mrs. Clemm, referring to her as “Muddy.”

Portrait of Frances Sargent Osgood
Portrait of Frances Sargent Osgood

Poe’s Scandalous Flirtation With Frances Sargent Osgood

Although Poe was devoted to his wife, he was not above demonstrating his attraction to at least one other woman. He had praised the writing of Frances Sargent Osgood both in print and in his lectures on American poetry.

As a result of Poe’s reviews, Osgood arranged an introduction, and the pair hit it off. Afterward, they exchanged poems of loss and longing in the pages of the Broadway Journal. At the time, Poe was an editor at the magazine.

This literary flirtation continued in public and private. Notably, Virginia was well aware of her husband’s and Osgood’s mutual attraction. In fact, Poe shared the poems and letters he and Osgood exchanged.

Osgood’s marriage was in a state of flux. Her husband, Samuel Stillman Osgood, was a painter and adventurer. As a result, he traveled frequently, often going on painting expeditions.. That left his wife free to pursue flirtations with other men.

According to The Edgar Allan Poe Society of Baltimore, everything came to a head when another writer, Elizabeth Ellet, developed a crush on Poe. Ellet publicly implied that Osgood and Poe were in a relationship. The result was that Poe distanced himself from both women.

A Bonus Mystery Hidden in a Poem

Like Poe’s death, his relationships with the loves in his life are something of a mystery. Each raises questions about their nature. Were they affairs? Were they platonic? Or were they objects of his unrequited love?

In at least one case, Poe left a hidden code inside a poem. Can you decipher who this poem is about?

A Valentine

For her this rhyme is penned, whose luminous eyes,

         Brightly expressive as the twins of Loeda,

     Shall find her own sweet name, that, nestling lies

         Upon the page, enwrapped from every reader.

     Search narrowly the lines!—they hold a treasure

         Divine—a talisman—an amulet

     That must be worn at heart. Search well the measure—

         The words—the syllables! Do not forget

     The trivialest point, or you may lose your labor!

         And yet there is in this no Gordian knot

     Which one might not undo without a sabre,

         If one could merely comprehend the plot.

     Enwritten upon the leaf where now are peering

         Eyes scintillating soul, there lie perdus

     Three eloquent words oft uttered in the hearing

         Of poets, by poets—as the name is a poet’s, too.

     Its letters, although naturally lying

         Like the knight Pinto—Mendez Ferdinando—

     Still form a synonym for Truth—Cease trying!

         You will not read the riddle, though you do the best you can do.

You can find the answer here.