Amazing conversation!

If I were going to throw in my two cents and recommend one book to read as an overview of Judaism for the interested non Jew (or even Jew who may not be so into the heritage, but curious) I would say This is my God by Herman Wouk.

I read that book in college and it had a profound effect on me. It has the advantage of rather than hitting someone with a wall of information, it goes into what the day to day practice of Jewish philosophy is and what it is like to be observant. It’s much more intimate than many other intro books, and while it is clear that any topic brought up can be discussed much further and in much deeper depth, the example of “this principle applies to me, in this way, in my life” is very compelling. It does not overwhelm and it gets to the core of why bother in eloquent, simple and expressive language. Wouk is a novelist (a pretty good one too) not a rabbi or a Jewish scholar, though it is clear he is very learned. He is not out to create a survey course as much as a heartfelt discussion of what it all means to him and an explanation of what it is to others. It is one well versed person’s take from the heart, and because of that, it gives a compelling root foundation from which to explore further. It’s maybe 250 pages.

There is a lot of Kabballah floating around in this discussion too. My two cents on that is that it is impossible to go wrong with anything by either Akiva Tatz or Areyah Kaplan. Tatz is a medical doctor in addition to being a very well respected rabbi. His books are very accessible and easy to read
introductions to Jewish mysticism - that are still both kosher and not watered down or over simplified to the point that they are wrong.

Areyeh Kaplan unfortunately died much too young. However, his books are a treasure. He was a nuclear physicist from MIT in addition to being a rabbi and while his books are meant to be on the introductory level (and they are) they are introductory in the same way that the best physics lectures you ever had freshman year are introductory. Don’t let this scare you away from him! Real Kabballah is deeply mathematical and philosophical. Kabballah has its own vocabulary and its own set of deeply subtle and abstract concepts. Certain aspects of it are simply most clearly laid out like a mathematical argument and there is really no way around that. See it as a Feynman lectures for Kabballah. Inner Space by Kaplan is a full on consciousness raiser. I would start there before going to any of his translations of actual Kaballistic texts.

I would also be remiss to not mention Heschel. His book on prayer, or on the Shabbos is deeply philosophical and of the sort that you read a sentence, realize it was one of the more profound things you have ever read, and then you re-read it five times.

Past that, for just a simple overview R. Benjamin Blech wrote an idiots guide to Judaism (yes it is orange and in that series) but it is chock full of useful information.