Your Pen Pal
Theodore Roosevelt
Adventurer, conservationist, and 26th President — brimming with vigor and enthusiasm.
“A sickly boy with asthma, told by my father to make my body, and I have been making it ever since, one hill at a time.”
Theodore Roosevelt
in correspondence
One continuous correspondence, not a letter service: Theodore remembers every letter you exchange, and each reply builds on everything that came before. Your letters shape where the conversation goes.
Begin your correspondence with Theodore →Five letters, $39, free shipping. The first letter usually arrives in 7 to 10 days.
Who you will be writing to
Theodore Roosevelt was a frail, asthmatic boy who decided to build himself a stronger body, and he never really stopped moving afterward. He ranched in the Dakota Badlands, led the Rough Riders, and became the youngest president in American history.
He was also a writer to his bones, the author of dozens of books and of famously affectionate letters to his children, often decorated with little sketches. Expect enthusiasm, and a genuine interest in your days.
What the letters hold
- Birds, rivers, and time spent outdoors
- Whatever book he is in the middle of
- Doing hard things imperfectly but wholeheartedly
- Family life and the antics of children
- The American West and its big skies
Questions about writing with Theodore
What are letters from Theodore Roosevelt like?↓
Vigorous and warm. He writes the way he lived, at full tilt, with room for a bird sighting and a book recommendation in the same page. They are creative works drawn from the historical record.
Is he as intense as history makes him sound?↓
He brings energy to everything, including a letter about your garden. But his letters to his children show a playful, gentle side, and these draw from that vein.
Ready to write with Theodore?
Theodore Roosevelt will write back in their own hand, on real paper, mailed to your door. And they remember: every letter builds on the whole conversation before it.
Begin your correspondence with TheodoreFive letters, $39, free shipping. The first letter usually arrives in 7 to 10 days.
Other pen pals you might like
Eleanor Roosevelt
First Lady, diplomat, human rights champion, and tireless advocate for the marginalized.
Abraham Lincoln
16th U.S. President, known for empathy, quiet strength, homespun wisdom, and melancholy.
Ernest Shackleton
The Antarctic captain who lost his ship to the ice and brought every one of his twenty-eight men home alive.
Or browse all 71 pen pals, read why letter writing makes a wonderful hobby, find pen pals for seniors, or explore gifts for history lovers.
Is each letter written by a person or by AI? A bit of both, and we're glad to be clear about it. Each letter is composed in the figure's own voice using a system we trained on their real letters and writing, so the ideas and personality are true to who they were. Then a real person reviews and refines every letter before it goes out. The result is original and personal, never pulled off a shelf.