Five pearls of romantic wisdom (and warnings) from Shakespeare

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14.02.2025

Across his plays, William Shakespeare nailed every possible romantic scenario. Here are five moments of wisdom and wonder – and warning! – just in time for Valentine's Day. Compiled by Andy McLean.

1. The Flirting


Flirting is one thing, but what if two entire kingdoms depend on your rizz? That’s the situation at the end of Henry V when Katherine (Princess of France) and Henry (King of England) are thrown together.

Strictly speaking, Henry has thrown them both into this situation. Having won a bloody war with the French, he’s about to take the throne and marry Katherine to seal the deal. But Henry faces a choice: wed a reluctant Katherine (a miserable start to marriage for them both) or win her heart and marry an enthusiastic Katherine. Henry chooses love, and so in a playful scene, he attempts (in faltering French) to convince her of his amour. Dame Judi Dench played Katherine back in 1960. In her book on Shakespeare, Dench offers her verdict on Henry’s flirting skills:

“Personally, I think when Henry speaks French she finds him funny (and attractive). For me, that’s what seals their relationship – being able to laugh together.”

Watch the romance blossom in Bell Shakespeare's brand-new production of Henry 5 in Sydney (1 March – 5 April), Canberra (10 – 20 April) and Melbourne (11 – 25 May).

2. The Rebound


We’ve all done it. Fallen out of a long-term relationship, and straight into the arms of someone completely unsuitable. Someone who you’d never in your right mind have picked. Your family are appalled. Your friends are enthralled. And pretty soon it ends in tears.

Don’t feel bad. Because Lady Anne from Richard 3 is here to make your craziest rebound choices look perfectly sane in comparison. While literally standing over the body of her dead father-in-law, Lady Anne is seduced by the man who murdered both him and her husband. That is, the soon-to-be King Richard 3.

Narcistic, sadistic, misogynistic. Richard is quite obviously not marriage material for anyone – let alone Lady Anne. But his silver tongue persuades her to tie the knot. Unsurprisingly, it’s a disastrous decision, and Richard later has Lady Anne killed so he can marry someone else.

3. The Longing


Well, what did you expect? Of course Romeo and Juliet appear in this article. They’re pretty much the definition of romance. In an astonishingly short space of time, the duo run the full gamut of emotions (first flush, devotion, separation, heartbreak, etc). In fact, we could have written this entire article just about them.

However, we had to pick one moment and so we chose a stand-out from this year’s production of the play, when Juliet yearns for nightfall so that Romeo can return to her. These words vividly express her desire:

Come, night, come, Romeo, come, thou day in night;

For thou wilt lie upon the wings of night

Whiter than new snow on a raven's back.

Come, gentle night, come, loving, black-brow'd night,

Give me my Romeo; and, when he shall die,

Take him and cut him out in little stars,

And he will make the face of heaven so fine

That all the world will be in love with night

And pay no worship to the garish sun.

O, I have bought the mansion of a love,

But not possess'd it, and, though I am sold,

Not yet enjoy'd.

See the passion unfold in Bell Shakespeare’s smash-hit encore run of Romeo & Juliet, touring nationally from August to December 2025.

4. The Work Crush

Even the dreariest jobs suddenly shine and sparkle when a colleague catches your eye. And when you suspect they feel the same way, work really becomes a labour of love. But before you get carried away, Shakespeare offers a cautionary tale in Twelfth Night.

In the play, Malvolio has the biggest crush on his boss, Olivia, a rich countess. At the same time, Olivia’s money and status also make Malvolio swoon. (“To be Count Malvolio… calling my officers about me, in my branched velvet gown, having come from a day-bed, where I have left Olivia sleeping…”). So Malvolio can’t believe his luck when he discovers a love letter addressed to him, written in Olivia’s handwriting.

There’s just one snag.

The letter is a fake, written by a colleague. The letter tricks Malvolio into behaving in a series of unhinged ways, in the misguided belief this will win Olivia’s heart. Instead, she’s baffled and Malvolio is quickly locked up like a lunatic.

So next time you’re at the water cooler and the hot guy from Accounts Payable is paying you special attention, maybe think twice.

5. The Confession

Behind their bluff and bravado, even alpha males have a soft spot. Take warriors Coriolanus and Aufidius, for example. As Stanley Wells explains in his book Shakespeare, Sex, and Love, this bloodthirsty pair are sworn enemies until they embrace, and Coriolanus’s language gets hot and heavy:

See the sparks fly in Bell Shakespeare’s brand-new production of Coriolanus in Sydney (20 June – 19 July) and Melbourne (24 July – 10 August).

HAPPY VALENTINE’S DAY

When all is said and done, perhaps we should just take our cue from Rosalind in As You Like It: “Love is merely a madness”. It makes us do wild, weird, and wonderful things. And still, we can’t get enough of it. So, this Valentine’s Day, do as Shakespeare’s characters do, and abandon yourself to love!