When Romance Wasn't Really Romantic

History is full of romantic gestures that sound dreamy in a Jane Austen novel, but not so much when you picture them happening to you in real life. A lot of “classic romance” was shaped by power dynamics, social rules, and public pressure, and just wouldn't fly today. None of this is meant to cancel the past, but it is a reminder that context matters and so do boundaries. Here are 20 historical gestures that were framed as romantic then, but would definitely read as red flags today.

Lunt-Fontanne Theatre, New York City on Wikimedia

1. George IV Sending a Secret “Lover’s Eye” Portrait

In the late 1780s, the Prince of Wales (later George IV) reportedly sent Maria Fitzherbert a miniature painting of his eye as a secret love token. Apparently, sending "Lover’s Eye miniatures" to your crush was a thing back then, but today, receiving a disembodied eyeball portrait from someone who “won’t give up” might feel less romantic and more like, “Are you okay?” 

anonymous  on Wikimedia

2. Victorian Sweethearts Exchanging Hair Jewelry

In the 19th century, giving a lock of hair as jewelry was a common love token, especially in the Victorian era. These days, if someone hands you a bracelet made from their hair on the third date, you’re probably calling a friend on the way home. It’s sentimental, sure, but it also has strong “I kept a piece of you” energy that can land weird. 

Unknown artist on Wikimedia

3. Queen Victoria Keeping Prince Albert’s Hair on Her Person

Queen Victoria famously held onto Prince Albert’s hair as a constant personal keepsake after he died. As a private grief ritual, it’s understandable, but imagine a new partner discovering you carry your late love’s hair everywhere and refuse to talk about it. 

John Jabez Edwin Mayall on Wikimedia

4. Napoleon’s Intensely Possessive Love Letters to Joséphine

Napoleon’s letters to Joséphine are famous for being passionate, but they also show a strong streak of jealousy and emotional intensity. If someone you’re seeing sends messages that swing between devotion and suspicion, it stops feeling romantic pretty fast. Big feelings aren’t the problem, but trying to control a partner through guilt definitely is.

Jacques-Louis David on Wikimedia

5. Edward VIII Abdicating the Throne for Wallis Simpson

Edward VIII giving up the British throne to marry Wallis Simpson is often told as peak romance. In a modern relationship, a life-altering sacrifice that huge can come with an unspoken invoice later. If you ever feel like you can’t leave because someone “gave up everything” for you, that’s not love—that’s pressure. 

National Media Museum from UK on Wikimedia

6. Elizabeth Barrett Browning & Robert Browning’s Secret Elopement

Famous Victorian poets, Elizabeth Barrett Browning and Robert Browning married in secret and then left for Italy, in part to escape her controlling father’s opposition. It’s romantic on paper, but today “Let’s secretly run away and cut off your family” can sound like isolation, not devotion. Even when the family situation is complicated, healthy relationships usually don’t require disappearing acts. 

Unknown author on Wikimedia

7. Petrarch Writing Hundreds of Love Sonnets to Laura

Petrarch wrote hundreds of sonnets about “Laura,” turning her into a lifelong muse in a way that shaped European love poetry. What's weird is, while he likely glimpsed her at chuch in 1327, it's uncertain whether they ever actually spoke. What's more, the real life Laura was married with children. In 2026, writing an entire personal brand around someone who doesn't want you isn't charming—it's obsessive and creepy.

AlexanderMWinkler on Wikimedia

8. John Keats Demanding Letters 

Keats’ letters to Fanny Brawne can be beautiful, yet some passages are intensely needy and controlling in tone. If someone tells you to write “immediately” and frames your attention as the only cure for their misery, that’s a lot for a relationship to carry. It's the modern version of your partner getting angry when you don't text back right away.

William Hilton on Wikimedia

9. Italian “Serenata” Window Singing Before a Wedding

In parts of Italy, it was traditional for a man to sing outside a woman’s window as a public courtship gesture, sometimes right before the wedding. Today, showing up at someone’s home uninvited with an audience can feel less flattering and more like social pressure. If the person doesn’t want that attention, it stops being romantic instantly. The modern version only works when the invite is clear and enthusiastic.

Wilhelm von Gloeden on Wikimedia

10. Andrew Jackson Fighting a Duel After His Wife Was Insulted

In 1806, Andrew Jackson dueled Charles Dickinson after a dispute that involved insults aimed at Jackson’s wife, Rachel. In its time, this could be framed as “defending her honor,” but now it reads like violent impulse wrapped in romance. Even if you love loyalty, you probably don’t want a partner who solves jealousy with pistols.

Jengod on Wikimedia

11. Beethoven’s “Immortal Beloved” Letter 

Beethoven’s famous “Immortal Beloved” letter is a legendary romantic artifact, full of devotion and longing. In a modern relationship, that level of emotional dependence can feel overwhelming, especially early on. The line between passionate and possessive can get blurry when someone writes as if their life can’t function without your attention. 

Joseph Karl Stieler on Wikimedia

12. Richard Burton Buying Elizabeth Taylor a Massive Diamond

Richard Burton’s gift of the Taylor–Burton Diamond became an iconic “grand gesture” moment. Today, a jaw-dropping gift can still be sweet, but it can also raise the “love-bombing” question if it shows up too soon. When an expensive present feels like it’s meant to secure commitment, the romance starts to feel transactional. 

Studio publicity still on Wikimedia

13. Mark Antony’s “Donations of Alexandria” for Cleopatra

In 34 BCE, Mark Antony staged a lavish public ceremony in Alexandria that elevated Cleopatra’s status and “gifted” her and their children control over various territories. It was meant to look like epic devotion, but today it would read like reckless grandstanding. If someone’s romantic move is basically a public spectacle with life-altering consequences, that’s not charming, it’s alarming. 

unknown on Wikimedia

14. Early Modern “Chaperone” Courtship That Limited Real Choice

In early modern England, courtship could be heavily supervised and shaped by family expectations, with the couple's feelings hardly coming into consideration. When you translate that vibe to modern dating, it can look like a person who can’t make independent decisions or set boundaries with family. Romance doesn’t land well when it feels like a committee is running the relationship.

Laurie & Whittle on Wikimedia

15. Henry VIII Rewriting the Rules for Anne Boleyn

Henry VIII’s pursuit of Anne Boleyn contributed to the break with Rome and the English Reformation, which was a massive shift that led to wars and many deaths. In modern terms, that kind of scorched-earth devotion can turn into emotional leverage later. If someone expects lifetime loyalty because they made a huge sacrifice, you can end up trapped by guilt instead of connected by choice. 

Unknown author on Wikimedia

16. Oscar Wilde’s Over-the-Top Devotion to Lord Alfred Douglas

Oscar Wilde’s relationship with Lord Alfred Douglas included lavish gifts, intense letters, and a kind of “I’ll endure anything for you” commitment that spiraled into public scandal. In a modern context, a partner who keeps pouring money and reputation into someone who thrives on drama can feel less romantic and more like a warning sign. 

Napoleon Sarony on Wikimedia

17. The Shivaree

Shivarees (also called charivari) were rowdy community traditions where people would show up at newlyweds’ homes to make noise and “celebrate” them, sometimes without invitation. That might’ve been considered playful social bonding, but today it would feel like a boundary disaster. You’re allowed to want privacy after your wedding.

Jean Ignace Isidore Gérard Grandville on Wikimedia

18. Pushkin’s Fatal “Honor” Spiral Over Rumors

Alexander Pushkin’s story is often framed as romantic tragedy, but the reality was a public honor culture boiling over into real-life consequences. After rumors circulated about Pushkin's wife, Natalia Goncharova, being unfaithful with a frenchman, Georges-Charles de Heeckeren d'Anthès, Pushkin challenged him to a duel and fatally wounded him. In a modern relationship, a partner who treats gossip as grounds for dramatic retaliation is not “devoted,” they’re unstable. 

Pyotr Sokolov on Wikimedia

19. Abelard & Héloïse’s Secret Marriage

Medieval scholar Peter Abelard and Héloïse famously ended up in a secret marriage that was meant to protect Abelard’s career and reputation. In today’s world, “Let’s keep you hidden so I don’t lose status” would read like a giant warning sign. If someone’s version of romance requires you to shrink your life so they can keep theirs intact, that’s not devotion, it’s a red flag.

Charles Durupt on Wikimedia

20. Eric Clapton and George Harrison’s “Guitar Duel” Over Pattie Boyd

Okay so it may not have been a "fight to the death" duel with real pistols, but it's still grounds for an eye roll. There’s a well-known rock lore story that Eric Clapton and George Harrison once had a guitar “duel” connected to their complicated love triangle involving Pattie Boyd. Even if the details get exaggerated over time, the vibe is still pretty rough by modern standards, because turning someone into the prize in a rivalry is not romantic. 

Hit Parader magazine on Wikimedia