Grab the Tissue Box, Because these Historical Letters are Heartbreaking
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

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