Texts in Conversation

Ecclesiastes presents distinct perspectives on pleasure and meaning, describing enjoyment as both futile and worthwhile. Many early readers saw this tension as problematic, with tractate Shabbat in the Babylonian Talmud capturing a discussion of this issue and how to attempt to resolve its internal differences.
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Ecclesiastes 2:2

Hebrew Bible
1 I thought to myself, “Come now, I will try self-indulgent pleasure to see if it is worthwhile.” But I found that it also is futile. 2 I said of partying, “It is folly,”and of self-indulgent pleasure, “It accomplishes nothing!” 3 I thought deeply about the effects of indulging myself with wine(all the while my mind was guiding me with wisdom) and the effects of behaving foolishly, so that I might discover what is profitable for people to do on earth during the few days of their lives.
Date: 3rd Century B.C.E. (based on scholarly estimates) Source

Ecclesiastes 8:15

Hebrew Bible
14 Here is another enigma that occurs on earth: Sometimes there are righteous people who get what the wicked deserve, and sometimes there are wicked people who get what the righteous deserve. I said, “This also is an enigma.” 15 So I recommend the enjoyment of life, for there is nothing better on earth for a person to do except to eat, drink, and enjoy life. So joy will accompany him in his toil during the days of his life that God gives him on earth. 16 When I tried to gain wisdom and to observe the activity on earth—even though it prevents anyone from sleeping day or night—
Date: 3rd Century B.C.E. (based on scholarly estimates) Source

Shabbat 30b

Babylonian Talmud
Rabbinic
Since contradictions in Ecclesiastes were mentioned, the Gemara cites additional relevant sources. Rav Yehuda, son of Rav Shmuel bar Sheilat, said in the name of Rav: The Sages sought to suppress the book of Ecclesiastes and declare it apocryphal because its statements contradict each other and it is liable to confuse its readers. And why did they not suppress it? Because its beginning consists of matters of Torah and its end consists of matters of Torah. The ostensibly contradictory details are secondary to the essence of the book, which is Torah.
Date: 450-550 C.E. (based on scholarly estimates) Source
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Notes and References

#4431
"... The Book of Ecclesiastes abounds in inconsistency. Commentators count between twenty and thirty contradictions. The problem of internal contradictions in Qohelet has been addressed in a famous pericope in the Babylonian Talmud (b. Shabbat 30b) ... A book of philosophy that contradicts itself did not make sense to the classical rabbis, as R. Abraham Ibn Ezra explains in his commentary on Ecclesiastes 7:3: “It is well known that even the merest of thinkers will not compose a book in which he contradicts himself.” The rabbis therefore resolved the contradictions by assigning a different context to each apparently contradictory proposition ..."

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