History’s most powerful and poignant break-up letters

Posted by
Anna Brech
backgroundLayer 1
Add this article to your list of favourites
Handwritten letter

Break-ups are never easy, but a little eloquence can go a long way. Here, we take a look back at some of history’s most moving “Dear John” letters – well before an age where a simple WhatsApp did the job.

Forget the modern-day cowardice of ghosting; the best kind of break-ups are handled with verve and courage.

Nothing rivals the raw emotion of heartache, but if you can channel the bitterness and upset into some kind of acceptance, you have the chance to emerge a stronger person (whether you’re the one parting ways, or vice versa). 

You may also like

Research says this is the best way to get over a bad break-up

Not only that, but writing down your feelings is a potent form of therapy in itself. 

So, with 2020 coming fast on the horizon, we take a look at how to part ways with dignity. Want to engineer a new start? Take your lead from these, history’s boldest break-up letters.

“I shall miss you with passion and wild regret”

From Richard Burton to Elizabeth Taylor

Two of Hollywood’s biggest stars met and fell in love on the set of Cleopatra in the 1960s, when both were married to other people. Their affair caused an international scandal, and led to a long and tumultuous relationship in the limelight.

This 1973 letter was written by Burton after Taylor broke things off with him the first time around (they divorced a year later, before remarrying and divorcing a second time).

We love Burton’s graciousness in the face of defeat here: he is owning up to his mistakes, and even goes so far as to imagine a better partner for the woman he loves.

You may also like

Dealing with a breakup: “Why you should say congratulations, not sorry, after a breakup”

(via Letters of Note)

You’re off, by God!

I can barely believe it since I am so unaccustomed to anybody leaving me. But reflectively I wonder why nobody did so before. All I care about—honest to God—is that you are happy and I don’t much care who you’ll find happiness with. I mean as long as he’s a friendly bloke and treats you nice and kind. If he doesn’t I’ll come at him with a hammer and clinker. God’s eye may be on the sparrow but my eye will always be on you. Never forget your strange virtues. Never forget that underneath that veneer of raucous language is a remarkable and puritanical LADY. I am a smashing bore and why you’ve stuck by me so long is an indication of your loyalty. I shall miss you with passion and wild regret. 

“You really loved me, I know you did”

Oscar Wilde to Lord Alfred “Bosie” Douglas

Oscar Wilde was described as being consumed by his feelings for Lord Alfred “Bosie” Douglas, the Oxford graduate he met and fell in love with in 1891. Bosie’s father, the Marquess of Queensberry, was outraged by their relationship, and his campaign against Wilde contributed to the writer’s imprisonment for gross indecency four years later.

During his two years in jail, Bosie abandoned Wilde, and this letter was his response. His mixture of pain, bewilderment, hurt and denial will ring true for anyone who’s suffered betrayal in love.

You may also like

“I had my hair chopped off 10 days after a major break-up – but was it a good idea?”

(Via The Times)

There is, I know, one answer to all that I have said to you, and that is that you loved me: that all through those two and a half years during which the Fates were weaving into one scarlet pattern the threads of our divided lives you really loved me. Yes: I know you did. No matter what your conduct to me was I always felt that at heart you really did love me. Though I saw quite clearly that my position in the world of Art, the interest my personality had always excited, my money, the luxury in which I lived, the thousand and one things that went to make up a life so charmingly, and so wonderfully improbable as mine was, were, each and all of them, elements that fascinated you and made you cling to me; yet besides all this there was something more, some strange attraction for you: you loved me far better than you loved anybody else.

But you, like myself, have had a terrible tragedy in your life, though one of an entirely opposite character to mine. Do you want to learn what it was? It was this. In you Hate was always stronger than Love. 

“I’ll wait. When you’ll wish it, just tell”

From Simone de Beauvoir to Nelson Algren

Feminist philosopher Simone de Beauvoir and Chicago writer Nelson Algren met in 1947, and their transatlantic love affair quickly took on a power of its own. De Beauvoir was said to be crazy about the Pulitzer Prize winner, writing him letters of a passion and intensity that was unrivalled, even by her other lovers (including Jean-Paul Sartre).

This heart-wrenching missive was penned in September 1950 as de Beauvoir made her way back to Paris after seeing Algren, and having sensed that his feelings for her had cooled. It’s beautiful for the way in which she attempts to tiptoe a fine line between expressing her desire for her lover, and not crowding him with it.

Not many people would be prepared to make themselves vulnerable like this after a break-up, but de Beauvoir puts all her cards on the table. 

You may also like

How I reclaimed Paris, City of Love, for myself after an earth-shattering break-up


I am not sad. Rather stunned, very far away fro myself, not really believing you are now so far, so far, you so near. I want to tell you only two things before leaving, and then I’ll not speak about it any more, I promise. First, I hope so much, I want and need so much to see you again, some day. But, remember, please, I shall never more ask to see you—not from any pride since I have none with you, as you know, but our meeting will mean something only when you wish it. So, I’ll wait. When you’ll wish it, just tell. I shall not assume that you love me anew, not even that you have to sleep with me, and we have not to stay together such a long time—just as you feel, and when you feel. But know that I’ll always long for your asking me. 

“I guess I’m not in love with you”

From Jackie Kennedy to her teenage boyfriend

The first cut is the deepest, a fact a teenage Jackie Kennedy knew well when she turned out this deft letter of rejection to her high school boyfriend (name unknown).

Written in 1946, the letter lays out in plain but not unkind terms why their young relationship won’t work. We like to think it sets the tone for the confident and poised First Lady who was to emerge in later years.

The letter was auctioned as part of a set of Kennedy’s handwritten letters for over £100,000 by Christie’s in 2015.

You may also like

Laverne Cox just taught us an essential lesson about self-care after a break-up

(Via Elite Daily)

I’ve always thought of being in love as willing to do anything for the other person — starve to buy them bread and not mind living in Siberia with them — and I’ve always thought that every minute away from them would be hell — so looking at it that [way] I guess I’m not in love with you. I do love you though — and can love you without kissing you every time I see you and I hope you understand that.

Images: Getty

Sign up for workouts, nutritious recipes and expert tips, plus our Strong Women magazine with expert advice on building strength & resilience sent to your inbox.

By entering my email I agree to Stylist’s Privacy Policy


Share this article


Anna Brech

Anna Brech is a freelance journalist and former editor for Her six-year stint on the site saw her develop a vociferous appetite for live Analytics, feminist opinion and good-quality gin in roughly equal measure. She enjoys writing across all areas of women’s lifestyle content but has a soft spot for books and escapist travel content.

Recommended by Anna Brech


Emma Thompson reveals how her own heartbreak inspired THAT Love Actually scene

“I knew what it was like to find the necklace that wasn’t meant for me.”

Posted by
Susan Devaney

“I went to see a psychic after my break-up – and it was bloody awful”

Think crystal balls, tarot cards and unexpectedly awkward trances…

Posted by
Kayleigh Dray

History's most powerful and poignant letters and diary entries

From Anne Frank to John Diamond

Posted by
Anna Brech

The 29 books everyone will be raving about in 2020

Hilary Mantel, Eimear McBride, Layla Saad – here are the new books to pre-order now.

Posted by
Francesca Brown

Jessie J’s self-care advice is a vital read for anyone nursing a broken heart

“Walk away from people or situations that trigger parts of you that are unhealthy,” advises Jessie J.

Posted by
Kayleigh Dray