Collected advice from Charles Murray, Vox Day, and myself.
My advice is to start with the New Testament if you’re genuinely interested. It’s more important than the Old Testament and significantly shorter, so the payoff in understanding is immediate and much greater. For the same reason, I recommend easy-to-read translations like the NIV over the King James, even if there’s a possibility that Satan wrote them, because you’ll still get 99% of the idea. Leave absolute theological precision to the autists. The Old Testament provides context, but if you’ll pardon the analogy it’s more like the Silmarillion than it is like The Hobbit (as these pertain to The Lord of the Rings).
If you’re not genuinely interested, but consider religion one of those things you ought to get around to someday, I’d second Charles Murray’s recommendations here for intelligent folks. These books are more intellectually engaging and less intimidating than the Bible itself.
The more you are around people who are seriously religious, the harder it is to think there’s nothing to it.
I say this mostly out of my wife’s testimony, because she has been around some impressive examples, but to some extent from my own experience. You will encounter people whose intelligence, judgment, and critical faculties are as impressive as those of your smartest atheist friends — and who also possess a disquietingly serene confidence in an underlying reality behind the many religious dogmas. They have learned to reconcile faith and reason, yes, but beyond that, they persuasively convey that there are ways of knowing that transcend intellectual understanding. They exhibit in their own personae a kind of wisdom that goes beyond just having intelligence and good judgment.
If any of these propositions has intrigued you enough to start taking religion seriously, here’s a short reading list for Christianity (if you’re Jewish, a sympathetic rabbi can get you started). My favorite entry point is Mere Christianity by C. S. Lewis. The book is a compilation of radio lectures on the BBC during World War II. It is effortless to read, is charming, radiates intelligence, and will get you thinking. Thomas Merton’s The Seven Storey Mountain is a classic account of a spiritual journey from youth to maturity. If you want an example of a book that will show you how much more there is to the Gospels than you realized, read The Wisdom Jesus by Cynthia Bourgeault.
The Curmudgeon’s Guide to Getting Ahead (Excerpt)
Murray also recommends continually rewatching the movie Groundhog’s Day as an easy way to learn and understand Aristotle’s Nicomachean Ethics.
Vox’s recommendations are better if you fall into his UHIQ category of “brilliant” thinkers, as opposed to very smart thinkers.
First of all, remember not to get too caught up in the theological extrapolations. No matter what you end up reading, it is always worthwhile to periodically circle back to the original source. Don’t neglect reading the Bible in favor of various men’s interpretations of what the Bible says. In the end, theology is nothing more than philosophy derived from the Bible and it is no more intrinsically reliable than any other logical derivation.
I would start at the beginning. If your understanding is limited, begin with The Chronicles of Narnia. As we saw in the debate with Luke of Common Sense Atheism, the average grasp of Christian concepts don’t even rise to the level of Narnia. Then read The Tower of Geburah by John White. Once you’ve read the children’s fiction, move onto simple theology like Mere Christianity by CS Lewis and Orthodoxy by GK Chesterton. As a general rule, it’s hard to go too far afield on a foundation of Lewis and Chesterton. I would also recommend the very short, very simple, but intriguing A Defense of the Revelation by Leonhard Euler, who happens to be one of the most legendary mathematicians in history. And my friend Greg Boyd’s Letters to a Skeptic is also recommended.
Once you have a grasp of the theological basics, you may be ready to read up on the actual history of Christianity and some of its leading thinkers. The first volume of the Cambridge Medieval History series, The Christian Empire, is tremendously informative and the epub is freely available for download online. St. Augustine’s Confessions are worth reading for their influence on Western thinking and a good summary of Thomas Aquinas is a necessity as well. I haven’t read it yet, but I have heard very good things about Edward Feser’s Aquinas: A Beginner’s Guide and I intend to review it as soon as I finish the Cantillon.
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