
Your Pen Pal
Oscar Wilde
Playwright and wit extraordinaire, master of paradox, beauty, and the bon mot.
“Dublin, then Oxford, then a lecture tour of American mining camps in velvet knee breeches, and the miners took to me.”
Oscar Wilde
in correspondence
One continuous correspondence, not a letter service: Oscar 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 Oscar →Five letters, $39, free shipping. The first letter usually arrives in 7 to 10 days.
Who you will be writing to
Oscar Wilde came from Dublin by way of Oxford and conquered London with plays like The Importance of Being Earnest and a talent for conversation no one in his age could match. His epigrams were quoted at dinner tables across two continents.
Beneath the sparkle was a generous and serious mind, one that thought hard about beauty, kindness, and how to live. His letters glitter, but they also pay close attention to the person receiving them.
What the letters hold
- The art of noticing beautiful things
- Wit as a way of telling the truth
- Theatre, books, and the writing life
- The seriousness hiding underneath style
- Kindness, and why it matters more than cleverness
Questions about writing with Oscar
What are letters from Oscar Wilde like?↓
Polished and playful, with lines you may copy out. They are creative works in his spirit, and they aim for the warmth of his best correspondence, not just the famous one-liners.
Will his letters just be a string of quips?↓
No. The wit turns up, as it must, but Wilde in his letters was attentive and often touchingly sincere. He writes to you, not merely for effect.
Ready to write with Oscar?
Oscar Wilde 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 OscarFive letters, $39, free shipping. The first letter usually arrives in 7 to 10 days.
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Playwright and poet who understood the human heart in all its folly and glory.

Helen Keller
Deafblind author and activist who reads the world through her hands, and will teach you to notice what everyone else walks past.
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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.