WordPress wants to know which author I’d love to have dinner with.
My first question is whether WordPress is also providing the time machine. Because if we’re doing this right, I’m not limiting myself to authors who are still alive. And once you open that door, the guest list gets complicated in a hurry.
Edgar Allan Poe would be fascinating. I’ve always been intrigued by the way his mind worked. The darkness, the atmosphere, the psychological tension—there was genius there. But I’m not sure I’d want to spend an entire evening too close to the madness that seemed to travel with it. Some artists are probably more appealing from a safe historical distance.
Stephen King would be another easy choice. I’d want to talk about plot development, suspense and the psychological layers he builds into his stories. He has an incredible ability to make something terrifying feel believable because the people inside the story feel believable first. I’d probably spend half the dinner asking how much of that is planned and how much simply develops as he writes.
Mark Twain might be the most fun.
He was funny, sarcastic, observant and far deeper than the humor alone would suggest. He understood hypocrisy, culture and human nature, and he knew how to make readers laugh while slipping something much more serious past them. I have a feeling dinner with Twain would be one long conversation you’d wish somebody had recorded.
Then there’s Ernest Hemingway.
That one would probably begin as a writing seminar and gradually become a terrible personal decision. I’d love to hear him talk about economy, discipline and cutting away everything that doesn’t belong. I’d also love to sit across a table from him with a good pour and listen to whatever stories came out.
The problem is that Hemingway would almost certainly be better at drinking than I am. And I know myself well enough to know I’d probably try to keep up. Hopefully I’d get a few good nuggets about writing before I passed out.
The Apostle Paul would also be on the list, although for very different reasons. That dinner wouldn’t really be about literary technique. Christians believe Paul wrote under the inspiration of the Holy Spirit, so I’m not sure I’d be sitting there asking him about sentence structure.
I’d be asking him to explain Romans. And Corinthians. And probably a few dozen things Christians have been arguing about ever since.
But if I had to choose just one, I think I’d probably land on C.S. Lewis.
The range alone is astonishing. The Chronicles of Narnia were pure genius. The Screwtape Letters came from an entirely different angle, but they were just as brilliant. Lewis could take theology, imagination, psychology and storytelling and somehow make them work together without making the result feel forced.
That’s rare.
I think dinner with Lewis would feel like a college education compressed into a couple of hours. I’d want to ask him how he built stories that worked on one level for children and another for adults. I’d want to know how much symbolism he planned and how much simply emerged. I’d want to hear him talk about faith, doubt, grief, imagination and the responsibility of a Christian writer.
And unlike the Hemingway dinner, there’s at least a reasonable chance I’d remember everything the next morning.
So that’s my answer. Assuming WordPress is taking care of the time machine.
Enjoyed this? Subscribe and get future reflections, bourbon notes, and assorted nonsense delivered straight to your inbox.
Copyright © 2026 Doug DeBolt.