I went down a rabbit hole recently and found myself deep in a video about medieval dating advice. Let me tell you, it was part hilarious, part terrifying, and strangely… familiar. You’d think we’ve come a long way in love since the days of jousting and herbal love potions, but honestly? Some of their old-school wisdom doesn’t feel that far off from today’s dating chaos.

For example, one of the medieval tips was to wear your lover’s colours during a tournament to show loyalty. I laughed at first—until I realised we still do this. We wear their hoodie, post couple selfies, and subtly tag them in our stories. Same idea, less chainmail. Back then it was a badge of devotion. Now it’s a carefully curated digital performance.

There were also rules like “don’t show too much emotion too early or you’ll scare them off.” Sound familiar? Today it’s called “playing it cool.” Back then, showing too much passion too soon was considered poor taste. Now it’s just another TikTok dating rule: “don’t be too available, or you’ll seem desperate.” We really haven’t changed much. We’re still afraid of being too much, too fast—for fear of rejection.

Another bizarre medieval belief was that eating certain foods—like parsnips or fennel—could make you more desirable. Apparently, these were thought to boost your natural attractiveness. In 2025, we call it “clean eating” or “glow-up season,” but it’s the same underlying idea: change yourself to be more appealing to someone else. Even then, we were trying to earn love through self-improvement.

But the strangest one? Medieval love letters. They were long, poetic, and completely over-the-top. Men would write to women they’d never even met, describing how their beauty had wrecked them. Honestly, it sounded like the 1300s version of DMing a stranger with “you’re so gorgeous, I can’t stop thinking about you.” Creepy then, creepy now.

Yet, buried in all the weirdness, there were a few gems of wisdom. They believed in loyalty. In courtship. In taking your time. In love as a deep, honourable pursuit—not just a weekend plan or a swipe-right impulse. That’s something I think we’re missing a bit today. We’re so busy trying to protect ourselves or look cool that we forget what love is actually about—caring deeply for someone and showing it.

So maybe we don’t need to bring back the love potions or medieval matchmaking dances (although, I’d be keen for a themed singles night, let’s be honest). But maybe we could borrow a little of that old-school heart. The intentionality. The courage to say, “Hey, I think you’re special,” and mean it—without worrying how it’ll look to our followers.

Dating has always been messy. Whether it’s scribbled poems by candlelight or left-on-read text messages, the search for love has never been easy. But one thing’s for sure—at every point in history, people have wanted the same thing: to be chosen, to be known, and to feel like they matter.

This is Dating Dave, grateful I don’t have to win a joust to impress a date—but still out here fighting the good fight for real, lasting connection.