Sliding Into DMs, Medieval Edition: How Ancient Royals Outsourced Romance

Alright, picture this: you’re a royal. You’ve got power, riches, and a castle that probably has terrible heating.

But there’s a problem — flirting? Way beneath your status.

You can’t just waltz up to someone and say, “Hey, wanna go halfsies on a kingdom?” Nope.

That’s what courtiers, messengers, and a whole lot of unnecessary drama were for.

Back in the day, royal romance wasn’t just about love — it was a full-on, high-stakes business deal, complete with secret notes, middlemen, and occasionally, a war or two. So how exactly did kings and queens get their flirt on without breaking a sweat?

Buckle up, because we’re diving into history’s messiest love lives.

1. Royalty: The Original "Too Busy to Text Back" Crew

Modern dating can be exhausting, but at least no one is expecting you to marry a stranger for political stability. Ancient royals, however, had to keep their love lives strategic — because the wrong match could literally bring down an empire.

Rather than spending their time crafting the perfect pickup line, rulers would outsource all their flirting duties to professional smooth-talkers — courtiers.

These guys were basically the PR agents of medieval romance, responsible for buttering up potential spouses, securing alliances, and making sure the king didn’t accidentally marry his cousin (which, let’s be honest, still happened way too often).

But courtiers weren’t the only ones playing Cupid…

2. Medieval Wingmen: Messengers Carrying Love Letters & Drama

Think of medieval messengers as the human version of WhatsApp — except instead of double ticks, you got beheadings if you delivered bad news.

These messengers didn’t just pass notes; they carried entire relationships on their shoulders.

A royal couldn’t just text their crush — no, they had to sit down, dictate a letter full of poetic declarations (that were usually written by someone else, because let’s be real, kings weren’t exactly known for their literary skills), seal it with a fancy wax stamp, and then hope the messenger didn’t get lost or robbed along the way.

The best part? Often, the messenger bears the blame when things go wrong. Imagine ghosting someone, and instead of just ignoring texts, you had to publicly humiliate the poor dude who delivered them.

Brutal.

3. Love Letters Were Basically a Power Move

Nowadays, a text like “wyd?” at 2 AM is the peak of effort, but back then? Love letters were an art.

They were drenched in metaphors, Latin poetry, and over-the-top compliments that would make even the cringiest Tinder bio look subtle.

Take Henry VIII, for example. Before he started decapitating wives like it was a hobby, he was out here writing thirsty love letters to Anne Boleyn.

He called her his “entirely beloved” and got all poetic about missing her. Big simp energy.

And if a royal wanted to really flex? They’d send fancy gifts — jewels, exotic animals, or even entire cities.

Imagine getting a whole province as a romantic gesture. Makes chocolates and flowers seem kinda weak, huh?

4. When Romance = Political Strategy

For royals, falling in love was not only adorable but also a matter of national security.

Marriages were business transactions wrapped in wedding veils — alliances were made, treaties were signed, and sometimes, entire wars were avoided (or started) because of a royal wedding.

Take Eleanor of Aquitaine. Eleanor of Aquitaine, known as the Beyoncé of the medieval world, not only married two kings, Louis VII of France and Henry II of England, but also adeptly navigated power politics.

Her marriages weren’t just about love — they shaped the entire political map of Europe.

Meanwhile, Catherine of Aragon had to deal with Henry VIII’s nonsense because their marriage was supposed to keep England and Spain BFFs. Spoiler: it didn’t work.

5. The Ultimate Breakup Drama: Divorce, Exile, or War

Ghosting wasn’t an option for royals — if a marriage went bad, it usually ended in exile, imprisonment, or outright war.

Forget changing your relationship status online — these people had to literally rewrite history to move on.

Henry VIII again? Man was so desperate to dump Catherine of Aragon that he invented an entirely new branch of Christianity just to make it happen.

Talk about commitment (to avoiding commitment).

And if divorce wasn’t an option, there was always the classic “mysterious death” route.

Poison, staged accidents, or just a good old-fashioned battlefield duel — anything to avoid an awkward conversation.

So, Was Outsourcing Romance a Win or a Fail?

On one hand, royal matchmaking took all the awkward small talk out of dating. No swiping, no bad first dates, no weird “u up?” texts.

Just a bunch of well-dressed middlemen handling all the details.

On the other hand? Yikes. The stakes were significantly elevated.

If things went wrong, you weren’t just left on read — you were left dead.

So, next time you complain about dating apps, just remember: at least you don’t have to worry about accidentally starting a war over your love life.