Midras Ulangan 23:23: Ein Yaakov (Glick Edition), Kohelet Rabbah, Midrash Tanchuma Buber & Vayikra Rabbah

וְכִ֥י תֶחְדַּ֖ל לִנְדֹּ֑ר לֹֽא־יִהְיֶ֥ה בְךָ֖ חֵֽטְא׃

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Ein Yaakov (Glick Edition)

Samuel said: "Whoever makes a vow, although he fulfills it, is to be termed wicked." Said R. Abba: "What is the passage to prove it? (Deut. 23, 23) But if thou forbear to vow, it shall be no sin in thee. We infer through the similar words chadala, chadaly (forbear) it is written here thechdal, and again it is written there (Job 3, 17) There the wicked cease (chadlu) from troubling."
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Kohelet Rabbah

“It is better that you do not vow, than that you vow and do not pay” (Ecclesiastes 5:4).
“It is better that you do not vow” – Rabbi Meir said: Better than both is one who does not vow at all, but rather brings his sheep to the Temple Courtyard, consecrates it, and slaughters it, as it is stated: “If you refrain from vowing, [there will be no sin in you]” (Deuteronomy 23:23).
Rabbi Huna said: There was an incident involving one who vowed and did not pay. He set sail in the Mediterranean Sea, and his ship sank in the sea and he died. Rabbi Shmuel said: Anyone who vows and does not pay causes for himself that his wife will die, as it is written: “I, when I came from Padan, Rachel died on me…” (Genesis 48:7).
Rabbi Shmuel bar Yitzḥak said: Anyone who vows and does not pay causes [himself] to come to four transgressions: Idol worship, forbidden sexual relations, bloodshed, and slander, and all of them are derived from Jacob.10While fleeing Esau, Jacob took a vow that he was to fulfill upon his return to Canaan (see Genesis 28:20–22), but he did not fulfill it immediately upon his return. Idol worship, as it is written: “Remove the foreign gods” (Genesis 35:2). Forbidden sexual relations, as it is written: “That he had defiled Dina his daughter” (Genesis 34:5). Bloodshed, as it is written: “Jacob’s two sons, […each] took [his sword…and killed all the males]” (Genesis 34:25). And slander, as it is written: “He heard the words of Laban’s sons [saying: Jacob has taken everything that was our father’s]” (Genesis 31:1).
Rabbi Mana said: Anyone who vows and does not pay causes death to come upon him, as it is stated: “For the Lord your God will demand it of you [and it will be a sin for you]” (Deuteronomy 23:22), and Rabbi Ami said: There is no death without sin, and there is no suffering without iniquity. There is no death without sin, as it is stated: “The soul that sins, it will die” (Ezekiel 18:4). And there is no suffering without iniquity, as it is stated: “I will punish their transgressions with a rod and their iniquity with plagues” (Psalms 89:33).
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Midrash Tanchuma Buber

Another interpretation (of Deut. 3:23): I BESOUGHT <THE LORD>. This text is related (to Is. 30:19): INDEED, O PEOPLE IN ZION, INHABITANTS OF JERUSALEM, [YOU SHALL SURELY WEEP NO MORE. <HE WILL SURELY SHOW YOU COMPASSION (rt.: HNN)>…. ] What is written above on the matter (in Deut. 3:12)?15Tanh., Deut. 2:4. <…> AND ITS CITIES I GAVE {TO THE CHILDREN OF REUBEN AND TO THE CHILDREN OF GAD} [TO THE REUBENITES AND TO THE GADITES]. Moses taught <all> who come into the world that one should not say that, whereas he is dangerously ill, has made a will,16Gk.: diatheke. and divided all that he has. He should not say that, whereas he has made a will, he will no longer pray. Rather he should pray, because the Holy One does not disqualify the prayer of [any] creature. See here. Moses made a will, as stated (in Deut. 23:12): < … > AND ITS CITIES I GAVE TO THE REUBENITES AND TO THE GADITES [….: (vs. 14:) JAIR BEN MANASSEH <RECEIVED>…. (vs. 15:)TO MACHIR I GAVE GILEAD. (vs. 16:) AND TO THE REUBENITES AND THE GADITES I GAVE [….: (vs. 18:) THEN I CHARGED YOU AT THAT TIME, SAYING [….] (vs. 21:) I ALSO CHARGED JOSHUA [AT THAT TIME], SAYING: [Ergo, <Moses made> a will. Lest you say: He ceased and did not pray, the text reads (in vs. 23) I BESOUGHT THE LORD.]
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