Grab the Tissue Box, Because these Historical Letters are Heartbreaking

Grab the Tissue Box, Because these Historical Letters are Heartbreaking

Shannon Quinn - October 31, 2022

Long before texting existed, people wrote letters to one another to express their deepest thoughts and emotions with the people they loved. Sometimes, an old letter can be as simple as learning what that person did with their day. Other times, it’s a way to look into the hearts and souls of the people that lived long ago. Here at History Collection, we have pulled together some of the most heartbreaking letters from the past.

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
A letter written by Titanic survivor. From Nellie Walcroft. Credit: Diary File

Letter from a Titanic Survivor Describing that Fateful Night (Part 1)

A Titanic survivor named Nellie Walcroft wrote a letter to her friend Clara, describing what happened the night the ship sank on April 15, 1912. This letter was written when Nellie was safely back in New York City. The original letter was three pages long, but we have shortened it for the sake of this article.

“My dearest Clara,

Just a line or two just to let you know we are quite safe. I am glad to say my cold is the only ill effect so far. To see that magnificent ship like a floating palace go down in the sea was an awful spectacle.

We had 70ft to be let down in the boat and when we were going down the steerage passenger jumped in the boat. And our officer, seeing our danger, jumped in the boat and shot the men to keep them from swamping us. When nearly to the bottom, the ropes letting the lifeboats down refused to act and they had to cut the rope and we dropped. I thought that was my last minute. There were 59 in our boat. After the ship had gone down you should have heard the cries of those poor men and women. I could never describe it. It seemed to last about 2 hours- that terrible cry of help…

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Survivors from the Titanic on a row boat. Credit: Wikimedia Commons

Titanic Survivor Nellie Walcroft’s Letter (Part 2)

“After the ship had gone down we had to change our boats to let our officer go back to the rescue and when we got into the boat there were 4 dead men and a madman. I think they pushed him overboard. I never saw him again. After rowing for 7 hours we got picked up by the Carpathia. We shouted for joy when we saw the ship. They took us up with ropes & gave us all neat brandy.

There were 710 rescued so that could not put us all up so we slept on tables for 5 days. They were very kind to us indeed in every way. The suffering was frightful. We had 35 women who had lost their husbands on board and one can imagine the agony of these women not knowing if their husbands were living or dead and how glad we were to see New York.

I had a fever here. We were given some clothes directly. We came off a steamer with 100 coffins waiting for the dead but most that died were buried at sea. The flashlights took our photo. I was so glad to meet Carl and his friend they soon got cab and we were snap shotted everywhere. There were 70.000 persons roped off in charge of the police. They were all where (sic) so glad to see us & the world sympathy is ours in New York. But I shall never never go on a floating palace again.

Write to me soon and send me any recipes you have got there.

With much love, your loving friend, Nell.”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Pauline Elliot wrote letters to her husband Frank during WWII. Credit: The Washington Post

The Elliot WWII Love Letters (Part 1)

During World War II, a woman named Pauline Elliott wrote letters to her husband Frank. He was killed on D-Day; June 6, 1944. Pauline held on to all of their letters that they had sent to one another throughout the war. Their daughter, DeRonda “Dee” Elliott, uncovered the letters after her mother died, and she was blown away by the tragedy and the romance. These letters were later published in American Heritage magazine, and they were even quoted during a speech by Bill Clinton. There are a total of 7 letters available, which can be read on The Washington Post.

“May 6, 1944

Dearest Darling,

All day I have been fighting the feeling which has been dominating me of late. I keep continually thinking of home and longing for home in the worst way. All your letters of how beautiful my daughter is becoming by the day. The realization that I am missing all these months and years of her formative growth is actually gnawing at my heart. . . .

I love you,


Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Troops on D-Day. The Star

The Elliot WWII Love Letters (Part 2)

“May 28, 1944


Here it is Sunday again. I think this is the most lonely time of the whole week for me. I am so darn lonesome for you, Frank darling. Oh I’m not the only one and I know it — there are millions just like me, wishing with all the strength of their hearts and minds for the return of peace and loved ones. — Dee is sleeping on this Sunday night, and the radio is playing old and beautiful music — and I am thinking of the Sunday nights to come when you will be listening to such music with me. — Took Dad to a ball game today — Dee went along — maybe she’ll learn to like baseball as well as her Daddy does — I’ll bet that she will.

I adore you,


Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Letters from World War II correspondence. Credit: Midcentury Modern Mag

“The Moon Shines On You, Too”

Here is another love letter from Pauline Elliot to her husband Frank, which was written on June 5, 1944. The truly tragic thing about this letter is that it was written the day before he died. So there was no way that Frank would have ever seen this letter.

“June 5, 1944


This is a beautiful summer evening, darling. I am sitting at the kitchen table (and not even noticing the noise of the refrigerator) from which place by merely lifting my head and looking out the window, I can gaze upon a truly silvery, full moon. It’s beautiful, dear — really beautiful, and it has succeeded in making me very sentimental. I had begun to think that I was becoming immune to the moon’s enchantment — so often I have looked at it without you and to keep myself from going mad told myself “It’s pretty, yes — but, so what?”

That’s not the way it really is though, darling — the sight of that shining moon up there — the moon that shines on you, too — fills me with romance — ; and even though it’s just a dream now, it’s a promise of a glorious future with one I love more than life. The darned old moon keeps shining for us, darling — and even as it now increases that inescapable loneliness, it also increases my confidence in the future.

I truly love you”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Oscar Wilde and Lord Alfred Douglas. Credit: Wikimedia Commons

“You really loved me, I know you did”

The famous author Oscar Wilde was in love with a man named Lord Alfred “Bosie” Douglas. Homosexuality was illegal at the time, and there was a huge stigma against the LGBTQ community. So they had to have a secret relationship. Alfred’s father, the Marquess of Queensberry, found out about their secret love. So Oscar Wilde was put in prison for “gross indecency” for four years because of it, while Alfred served two. During this time, he decided to end their relationship. This letter was Oscar’s response.

“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.”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Richard Burton and Elizabeth Taylor. Credit: Wikimedia Commons

“I Shall Miss You With Passion and Wild Regret”

This letter was written by Richard Burton to his ex-wife Elizabeth Taylor. When they first met, they were working together on the set of the Hollywood movie Cleopatra in 1960. At the time, they were both already married, but fell in love and left their respective spouses for one another. Burton and Taylor actually divorced twice. This was their first divorce, before getting back together and remarrying later on.

“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. So I shall miss you with passion and wild regret.”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
The beautiful philosopher Simone de Beauvoir. Credit: The Paris Review

“I Shall Not Assume That You Love Me Anew”

This next letter is from Simone de Beauvoir to her former lover, Nelson Algren. During their relationship, it’s clear that she loved him with a fiery passion. But after their breakup, she wanted to let him know that she still loved him without being too smothering or clingy. She even mentions that if they ever sleep together again, she won’t assume that it means he loves her. This was her response to their breakup.

“I am not sad. Rather stunned, very far away from myself, not really believing you are now so far. And I want to tell you only two things before leaving, and then I’ll not speak about it any more, I promise. First, I want and need so much to see you again, some day. But, remember, please, I shall never 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. 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.”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Young Jackie Kennedy. Credit: Town and Country

“I guess I’m not in love with you”

This letter was written by Jackie Kennedy when she was breaking up with her High School boyfriend. The identity of the boyfriend is unknown. But this became such a popular letter, that it actually sold at auction at Christie’s for $100,000 in 2015.

“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.”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
Novelist Thomas Wolfe wrote a letter to his friend and editor before he died. Credit: Wikimedia Commons

“I Know I’m Just a Grain of Dust”

In 1938, the famous novelist Thomas Wolfe went to the hospital with pneumonia, and was soon diagnosed with tuberculosis of the brain. He died just a few months later, when he was only 37 years old. While he was on his deathbed, Thomas wrote a letter to his friend and editor Maxwell Perkins, because they had a falling out, and he wanted to make amends before he died.

“August 12, 1938

Dear Max:

I’m sneaking this against orders, but I wanted to write to you.

I wanted most desperately to live, and I thought about you all a thousand times, and wanted to see you all again. There was the impossible anguish and regret of all the work I had not done. I know now I’m just a grain of dust, and I feel as if a great window has been opened on life I did not know about before. If I come through this, I hope to God I am a better man, and in some strange way I can’t explain, I know I am a deeper and a wiser one. If I get out of here, it will be months before I head back. But if I get on my feet, I’ll come back.

Whatever happens—I had this “hunch” and wanted to write to you and tell you, no matter what happens or has happened, I shall always think of you on that Fourth of July day three years ago when you met me at the boat. And we went out to the café on the river and had a drink and later went on top of the tall building, and all the strangeness and the glory and the power of life and of the city was below.

Yours always,


Grab the Tissue Box, Because these Historical Letters are Heartbreaking
This letter is from a grieving soldier to the man he loves. Credit: Pinterest


“Sleep Well, My Love”

This is a letter written by a man named Brian Keith, who served in World War II, to Dave, a man he met while serving in North Africa. They fell in love, but the two were separated and never able to see one another again, because Dave passed away. This letter was originally printed in ONE Magazine, a pro-gay magazine back in 1953.

“Dear Dave,

This is in memory of the anniversary of October 27th, 1943, when I first heard you singing in North Africa. That song brings memories of the happiest times I’ve ever known. A ring and promise given. The night of pouring rain and two very soaked GIs beneath a solitary tree on an African plain. A warm sulfur spring, the cool Mediterranean, and a picnic of rations and hot cokes.

One cold, windy night we crawled through the window of a GI theater and fell asleep on a cot backstage, locked in each other’s arms. The shock when we awoke and realized that miraculously we hadn’t been discovered. A fast drive to a cliff above the sea. Pictures taken, and a stop amid the purple grapes and cool leaves of a vineyard.

The happiness when we were told we were going home and the misery when we learned that we would not be going together. Fond goodbyes on a secluded beach beneath the star-studded velvet of an African night, and the tears that would not be stopped as I stood atop the sea-wall and watched your convoy disappear over the horizon.

We vowed we’d be together again “back home,” but fate knew better. You never got there. And so, Dave, I hope that wherever you are these memories are as precious to you as they are to me.

Goodnight, sleep well my love.

Brian Keith”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
This letter is from Frida Kahlo to her husband Diego Rivera. Credit: Wikimedia Commons

“I’m Amputating You”

Frida Kahlo is one of the most incredible female painters in history. She suffered with polio as well as a serious accident as a teenager that put her in a wheelchair. On top of that, her marriage to artist Diego Rivera was never easy. In this letter, just one year before her death, Frida is about to have her leg amputated due to a gangrene infection. She uses this as an opportunity to break up with Diego.


My dear Mr. Diego,

I’m writing this letter from a hospital room before I am admitted into the operating theater. When they told me it would be necessary to amputate, the news didn’t affect me the way everybody expected. I am not afraid of pain and you know it. It is almost inherent to my being. Although I confess that I suffered, and a great deal, when you cheated on me. Not just with my sister but with so many other women. Let’s not fool ourselves, Diego, I gave you everything that is humanly possible to offer and we both know that. But still, how the hell do you manage to seduce so many women when you’re such an ugly son of a bitch?

The reason why I’m writing is not to accuse you of anything more. It’s because I’m having a leg cut off. It’s not my intention to make you or anyone else feel pity. I’m writing to let you know I’m releasing you, I’m amputating you. Be happy and never seek me again. I don’t want to hear from you. If there is anything I’d enjoy before I die, it’d be not having to see your fucking horrible bastard face wandering around my garden.

That is all, I can now go to be chopped up in peace.

Your Frida”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
For hundreds of years, this letter from a widow to her dead husband survived in a South Korean tomb. Credit: Letters of Note

“How Could You Go Ahead of Me?”

In 1998, there was an excavation of a tomb in South Korea, and they uncovered the mummified body of a 30-year old man named Eung-Tae Lee. On his chest, there was a letter from his pregnant wife, who was grieving his death.

“June 1, 1586

You always said, ‘Dear, let’s live together until our hair turns gray and die on the same day.’ How could you pass away without me? Who should I and our little boy listen to and how should we live? How could you go ahead of me?

Whenever we lay down together you always told me, ‘Dear, do other people cherish and love each other like we do? Are they really like us?’ How could you leave all that behind?

I just cannot live without you. Please take me to where you are. I cannot forget in this world and my sorrow knows no limit. Where would I put my heart in now and how can I live with the child missing you?

Please look at this letter and tell me in detail in my dreams. Look closely and talk to me.

When I give birth to the child in me, who should it call father? Can anyone fathom how I feel? There is no tragedy like this under the sky. You are just in another place, and not in such deep grief as I am. There is no limit and end to my sorrows that I write roughly. I believe I can see you in my dreams. Come to me secretly and show yourself. There is no limit to what I want to say.”

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
This letter was from Alan Turning to his friend Norman Routledge. Credit: Wikimedia Commons

“Yours in Distress”

Alan Turing was a mathematician and one of the lead codebreakers during World War II. Many of you may have seen his life story in the movie The Imitation Game. In 1952, he was charged with “gross indecency” for having a homosexual relationship with another man. His punishment was either imprisonment or chemical castration. He chose castration. Just two years later, when he was 41 years old, he committed suicide. Here is a letter he wrote to his friend Norman Routledge just before he plead guilty to the charges.

“My dear Norman,

I don’t think I really do know much about jobs, except the one I had during the war. It certainly involved a good deal of hard thinking, but whether you’d be interested I don’t know. However I am not at present in a state in which I am able to concentrate well, for reasons explained in the next paragraph.

I’ve now got myself into the kind of trouble that I have always considered to be quite a possibility for me. Though I have usually rated it at about 10:1 against. I shall shortly be pleading guilty to a charge of sexual offences with a young man. The story of how it all came to be found out is a long and fascinating one, which I shall have to make into a short story one day.. No doubt I shall emerge from it all a different man, but quite who I’ve not found out.

I’m afraid that the following syllogism may be used by some in the future.

Turing believes machines think

Turing lies with men

Therefore machines do not think

Yours in distress,


Grab the Tissue Box, Because these Historical Letters are Heartbreaking

Grab the Tissue Box, Because these Historical Letters are Heartbreaking
The grave stone of a woman named Emmie who left a love letter behind. Credit: Letters of Note

“I Am Here in the Sunset”

At the Mount Auburn Cemetery in Massachusetts, this grave stone has an inscription of a love letter written by a woman named Emmie to the love she left behind.

“My Sweet Sumner,

I am very sorry that I had to go, it was simply my time. You were always the stronger of us. I could never have held the tiller for you as you did for me in such dark and ravaging seas. In my days of passage you were, as I knew you would be, perfect.

I have left the stage but I will never leave you. I am in a thousand places that will always be ours. Look for me in the sunsets, the ones that marry the light of a yawning day to the bright pink billowed clouds of a western sky. These are my sunsets not yours. Live my sweet Sumner, live with every ounce of love that you still have to give. Do not question this hunger that still rides within your warm and pounding heart. If you get lonely just look for me. I am there in the sunset, listen closely and I will whisper my blessing.

Forever Your Valentine,


Grab the Tissue Box, Because these Historical Letters are Heartbreaking
The tragic letter from a mother to the Navy. Credit: Letters of Note

“It Was Hard to Give Five Sons to the Navy”

“Waterloo, Iowa

January 1943

Bureau of Naval Personnel

Dear Sirs:

I am writing to you in regards to a rumor going around that my five sons were killed in action in November. A mother from here came and told me she got a letter from her son and he heard my five sons were killed.

It is all over town now, and I am so worried. My five sons joined the Navy together a year ago, Jan. 3, 1942. They are on the Cruiser, U.S.S. JUNEAU. The last I heard from them was Nov. 8th. That is, it was dated Nov 8th, U.S. Navy. Their names are, George T., Francis Henry, Joseph E., Madison A., and Albert L. If it is so, please let me know the truth.

I am to christen the U.S.S. TAWASA, Feb. 12th, at Portland, Oregon. If anything has happened to my five sons, I will still christen the ship as it was their wish that I do so. I hated to bother you, but it has worried me so that I wanted to know if it was true. So please tell me. It was hard to give five sons all at once to the Navy, but I am proud of my boys that they can serve and help protect their country. George and Francis served four years on the U.S.S. HOVEY, and I had the pleasure to go aboard their ship in 1937.

I am so happy the Navy has bestowed the honor on me to christen the U.S.S. TAWASA. My husband and daughter are going to Portland with me. I remain,


Mrs. Alleta Sullivan”


How did we find this stuff? Here are our sources:

WWII love letters tell of romance and tragedy. The Washington Post. 2015

Titanic Letter Archives. Diary File. 2022

History’s most powerful and poignant break-up letters. Stylist. 2000.

Letters of Note. 2022