Simcha H. Benyosef wrote a book called 'The Light of Ephraim'

Written as a series of counseling and teaching sessions between a troubled young couple and a mysterious Kabbalist, The Light of Ephraim is about self-growth, human relationships, and a quest for spiritual meaning.

I really enjoyed this book. What I liked most is how the author lets us inside a budding relationship between a master and his pupil. The dialogue, at times, had me convinced that I was the young man searching for answers and fulfillment.

Are there other books written such that they 'pull you into the conversation' in a story-like fashion while teaching?

This is not limited to Hashkafa/Mussar. Any topic in the master-student style is acceptable.

  • 1
    The Kuzari? – msh210 Dec 23 '15 at 5:31
  • Are you asking for any book in the style of master-student? – HaLeiVi Dec 23 '15 at 6:40
  • Allowed myself to broaden the question from singular to plural - feel free to reject the edit if you disagree – mbloch Dec 23 '15 at 7:46
  • Would Rav S.R. Hirsch's 19 letters qualify? – Danny Schoemann Dec 23 '15 at 9:00
  • Are you asking for specifically hashkafa/mussar works? – Loewian Dec 23 '15 at 16:05

To provide a couple more examples:

Da'as T'vunos by the Ramchal (mid-18th century)1 explores fundamental topics of Jewish thought in the style of a master-student dialogue between the intellect and the soul.

Ammudei Beis Y'huda by Yehuda Hurwitz (1766)2 uses a narrative approach involving discussions between two Jewish sages and an intelligent aborigine to present a defense and explanation of Judaism while also exposing some follies of Western culture. This narrative setting was copied by Voltaire in L'Ingénu in the following year.3

1 Feldheim's English translation by Shraga Silverstein (1982) is available for purchase here and available for limited preview on Google Books.

2 This work interestingly received approbations from both the Ashkenazi and Sepharadi Chief Rabbis of Amsterdam (R' Shaul Lowenstam and R' Shlomo Shalem, respectively) as well as a rare approbation from Moses Mendelssohn,

3 This little recognized instance of apparent narrative imitation of Jewish writings (across a religious/philosophical divide) in contemporaneous works of philosophical fiction may mirror an earlier possible instance in Rabbi Yehuda Halevi's The Kuzari (1140) and Peter Abelard's Dialogus Petri Baiolardi, which was left unfinished and has traditionally been dated to shortly before Abelard's death sometime between 1142 and 1144 (although some have speculated that Abelard wrote the work in the late 1130's, well before his death, there are multiple grounds to question that hypothesis - see the Introduction to Pierre Payer's translation of the work, pp. 6-10).

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  • You make my sentence about "older series of books" look very weird for books written in the 1990s :->> – mbloch Dec 23 '15 at 13:52
  • @mbloch I suppose so. :) I was actually thinking about R' Tauber's books, but when you answered I decided to cover other bases. – Fred Dec 28 '15 at 21:34

There is a slightly older series of books by R Ezriel Tauber in the same style of an older Rav teaching through questions and answers. Although the style is very readable, the answers are very profound.

See the full list here and here, key ones I read and liked were

Note that not all of his books are written in that style, e.g., As In Heaven So On Earth

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