BY G. CONNOR SALTER

William O’Flaherty is known to many in the C.S. Lewis scholarship community for his podcast All About Jack: A C.S. Lewis Podcast, his entertaining book The Misquotable C.S. Lewis, his website Essential C.S. Lewis, and the YouTube channel Knowing and Understanding C.S. Lewis. His latest book takes a more specific direction. The Screwtape Letter Handbook: The Easiest Guide to Get the Most Out of C.S. Lewis’ Classic Book is published through Winged Lion Press and has received endorsements from such noted authors as Patti Callahan (Becoming Mrs. Lewis).

O’Flaherty was kind enough to answer a few questions about the book.

Interview Questions

To clarify, is this an updated edition of your original book, ​​​C.S. Lewis Goes to Hell, or a wholly new book about The Screwtape Letters?

Believe it or not, The Screwtape Letters Handbook is more like a new book that adapts elements of the earlier Hell book from 2016. The original book not only had study questions (and suggested answers for most questions), but another major component was a “topical glossary.” That segment was something I was really proud of, but I thought I could improve on it. So, I approached the same publisher and suggested expanding and reorganizing it. I received the okay to proceed, and after considering a few other options, decided to keep it simple by creating a fresh summary of the letters themselves for this new book. The work I did in 2016 only had about five sentence-length statements for each letter. This time, I outlined each paragraph, so while still a summary, each of them is more than twice as long.

When did you first become aware of The Screwtape Letters?

I first read it in 1981. It was the second book by Lewis that I ever read. The first was The Lion, the Witch and the Wardrobe, which I read for an English class in high school. I honestly don’t recall if I realized there were more Narnia books, or if I wanted something different. So, I asked a salesperson at my local Christian bookstore, and he showed me The Screwtape Letters. I was immediately hooked. Partly because the letters are so short, but also because of the creative way Lewis offered advice without letting you know that he was offering advice for your life.

At what point did you move from being a fan of the book to deciding you wanted to write a book about it?

I attended a church back in the early 2000s where members of the Sunday School class I attended took turns teaching. When I volunteered, I decided that because I loved The Screwtape Letters so much, I would see if I could teach it. The members agreed. Back then, I wasn’t aware of any study guides other than a very short one that was at the end of the first copy of Screwtape I purchased. This drove me to create my own material, which served as the foundation for my first book on Screwtape, published in 2016.

What motivated you to return to the topic?

In the summer of 2024, I was scheduled to speak at an event called Inklings at Indy (hosted by the C.S. Lewis Society of Central Indiana), and I decided because I had been doing a short video feature on my YouTube channel called “Screwtape Saturday,” that I would adapt that adaptation into a talk. The material came from the topical glossary in the first book. As I worked with this content more, I noticed that some entries might benefit from expansion. Then the feedback from my talk was very positive and that’s when I considered doing what now has resulted in the new book.

I suspect for many first-time readers, the surprising thing about The Screwtape Letters is how amusing it is while addressing complex ideas. Do any chapters or quotes especially amuse you?

That’s the beauty of Lewis’s writings; he excels at addressing complex ideas in a way that is clear to the reader, and often it is done in such a whimsical way. In the fourth letter Wormwood is instructed about prayer and Screwtape calls it a “painful subject!” The average Christian doesn’t go around wondering what the devils think about prayer, but from their viewpoint, it must indeed be a painful or difficult topic to grasp. In the sixth letter the expression “maximum uncertainty” is used when addressing how to get the patient to worry about the future and what Lewis says through the voice of Screwtape is engaging and humorous at the same time. Then there is letter eleven, which is devoted to the four causes of laughter. That material is pure genius. Finally, I’ll mention the fourteenth letter, which is mostly about humility. One quote from it is this: “Your patient has become humble; have you drawn his attention to the fact? All virtues are less formidable to us once the man is aware that he has them, but this is specially true of humility.”

Some years ago, I did an informal study of books emulating The Screwtape Letters and noticed how few delved into the nuances and complexities of temptation as much as Lewis does. He’s not cynical, but he is pretty ruthless in describing how many mundane sins we commit all the time, or consider doing. Do any of the passages about temptation particularly strike you?

That’s a great point about how Lewis deals with the nuances and complexities of temptation in the letters. While he used the word temp/temptation/temptations in thirteen letters and once in the Toast essay, issues related to the topic are seen throughout the book. I found it interesting when he had Screwtape (in the twelfth letter) speak of a time when a person has drifted so much away from God that the devils don’t have to keep up “the tiresome business of providing Pleasures as temptations.” Then in the next letter, Wormwood is told when dealing with his patient that he must be on guard against those things that are more of a “strong personal taste which is not actually a sin” that can be used to protect them against useful temptations.

You’ve built an impressive record covering Inklings news, from interviews with scholars to commentating on new C.S. Lewis memes, which I’m sure presents plenty of challenges and rewards. What kind of things interest you enough to devote the extra time and write a book about it?

I merely love the works of Lewis so much that I’ll take any opportunity I can to interact with them. So, it might be interviewing others who have written about him, gently informing someone that the quote they shared on social media is interesting, but not by Lewis, or sitting down and writing a book…again…I’ll take any excuse to engage in the writings of C.S. Lewis.

Do you generally find it easier to discuss your ideas through writing or through talking about them (on a podcast, a video series, etc.)?

I find it easiest, most of the time, to put my ideas down in writing first so that I can discuss them in a meaningful way. That is, once I’ve thought through what I’m thinking, then I can express myself more clearly.

How does it feel to get praise from authors like Patti Callahan or Charlie W. Starr for your writing efforts?

It is truly an honor to have others like Patti and Charlie endorse my work. There are many others whom I respect that I’ve had the privilege to receive kind words about my writings. It is a very humbling experience.

Any other projects you would like to share?

As with most writers or other creative people, I have ideas popping up all the time. Some even stay in my mind long enough to write them down to consider if they are worth pursuing. I’ve been working on materials to help people who want to memorize Bible verses but struggle with success find a practical way to do it. Then, I came up with a “reverse devotional” a la Screwtape that I shared in April 2025 at the Inklings Fellowship retreat. I’m considering writing more of them, but I’m not sure I will have enough for a book.

Also, I have another very fresh idea, also related to Screwtape, that I haven’t yet had the time to run by some close Lewis scholars to see if they think I’ve lost my mind or came up with the next million-dollar seller. It’s probably somewhere in between!

Finally, having been diagnosed autistic only back in February 2024 at the age of 60, I’m considering at least creating a series of blog posts over at my website AdultAutismWithWilliam.com and that might eventually become a book.

The Screwtape Letter Handbook is available through Winged Lion Press.