Throughout history, love has inspired both beautiful poetry and horrifying obsessions. While we often romanticize historical love stories, many of the most famous romantic encounters from the past would be considered deeply disturbing by today's standards. These creepy dates in history reveal the dark side of human passion and the dangerous extremes people have gone to in the name of love.
When Romance Becomes Horror
The concept of creepy dates in history isn't just about awkward social encounters - it encompasses some of the most disturbing romantic behaviors ever documented. From necrophilia to obsessive stalking, these historical accounts show that inappropriate dating behavior is nothing new, though the extremes reached by some historical figures are truly shocking.
What makes these stories particularly unsettling is how many of these behaviors were normalized or even celebrated in their time periods. Many of the most famous "romantic" stories from history would be classified as stalking, harassment, or worse if they occurred today.
The Most Disturbing Historical Romance Stories
Carl Tanzler: The Ultimate Necrophilic Romance
In 1930s Key West, German doctor Carl Tanzler became obsessed with a young tuberculosis patient named Elena Milagro de Hoyos. When she died in 1931, Tanzler's grief transformed into something far more sinister. Two years after her death, he exhumed her corpse and took it home, where he lived with her decomposing body for seven years, dressing it up and attempting to preserve it with various chemicals and wax.
The case is documented in contemporaneous Key West newspaper coverage and later retellings, which is why the details above — the exhumation, the seven years, the charge that carried no jail time — are unusually well attested for a story this strange.
Mary Shelley's Graveyard Courtship
The author of Frankenstein had her own creepy dating story. As a teenager, Mary Godwin (later Shelley) would take her romantic interest, poet Percy Bysshe Shelley, to her mother's grave for their secret meetings. While Percy found this romantic as a fellow poet, most people would consider conducting a courtship in a cemetery to be deeply unsettling.
This represents one of the more "mild" creepy dates in history, but it demonstrates how different historical periods had vastly different ideas about appropriate romantic settings. The fact that Mary chose her deceased mother's grave as a romantic meeting spot speaks to both her unconventional upbringing and the gothic sensibilities of the Romantic era.
The graveyard meetings come from the Shelleys' own letters and the biographical work of Mary's later years, where she was unusually candid about their courtship — one of the few stories here documented primarily by its participants.
Leon Trotsky's Obsessive Pursuit
The Russian revolutionary's affair with artist Frida Kahlo quickly turned from passionate to pathetic. While Kahlo grew bored with the relationship, Trotsky became increasingly obsessed, sending her nine-page love letters that she found so annoying she forwarded them to friends, writing "I am very tired of the old man" - essentially the 1930s equivalent of sharing screenshots of a creepy ex's texts.
This story shows that even revolutionary leaders weren't immune to becoming the creepy older man in someone's dating history. Trotsky's inability to accept rejection and his increasingly desperate attempts to win back Kahlo's affection mirror many modern stalking behaviors.
Caligula's Incestuous "Dates"
Roman Emperor Caligula took creepy dates in history to an entirely new level with his alleged romantic relationships with his sisters, particularly Drusilla. Historical accounts suggest he not only had sexual relationships with all three of his sisters but also forced them to participate in public displays of affection that scandalized even the notoriously permissive Roman society.
One caveat worth knowing: the incest claims come from hostile ancient sources — Suetonius and Cassius Dio, both writing after Caligula's fall — while contemporaneous coins and records only show the sibling favoritism. Legend and record are tangled here in a way the other stories on this list are not.
Nero's Murderous Romance
Emperor Nero's relationship with his mother Agrippina was disturbing enough, but his romantic life became even more twisted when he fell in love with a young man named Sporus who resembled his deceased wife Poppaea. Nero had Sporus castrated and then "married" him in a public ceremony, forcing him to dress as Poppaea and act as his wife.
This represents one of the most psychologically disturbing creepy dates in history, as it combined elements of forced gender transformation, public humiliation, and necrophilic obsession with a deceased spouse. The fact that this was conducted by one of the most powerful men in the world makes it even more horrifying.
The Dark Side of "Romantic" Historical Practices
Many practices that were considered romantic in historical periods would be classified as deeply creepy today. These include:
- Arranged marriages between children and much older adults
- Kidnapping as a form of courtship (bride capture)
- Dueling to the death over romantic interests
- Keeping locks of hair or personal items from deceased lovers
- Public displays of grief that lasted for years
- Forced marriages as political alliances
Why These Stories Matter Today
Understanding these creepy dates in history helps us recognize how far society has come in terms of consent, healthy relationships, and appropriate boundaries. Many behaviors that were once considered passionate or romantic are now recognized as signs of mental illness, abuse, or criminal behavior.
These historical accounts also serve as cautionary tales about the dangers of unchecked power and obsession. Many of the worst examples of creepy dates in history involved people in positions of authority who used their power to pursue inappropriate relationships or engage in disturbing behaviors without consequences.
The pattern is recognizably the same whether it is an emperor or a modern date: obsessive interest that ignores the other person's signals, escalating boundaries tested one at a time, and power used to keep someone from leaving. Studying the extreme historical versions makes the modern, smaller-scale versions easier to spot — in your own life as much as in the news.
It is also why the theme shows up so often in fiction. Horror romance works precisely because the fear of an affection that will not let go is real; the game this site is about leans on the same instinct with its jealousy mechanics — but there, unlike in history, you can reload a save.
Explore Historical Horror Safely
Fascinated by these dark historical tales? Experience creepy dates in history through our interactive horror dating game, or branch into fiction with the game's creepypasta romance routes — and, if you want more after that, other dark visual novels like Creepy Dates.
Play Creepy Dates Game