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In בראשית ל"ח we have Yehuda sending his pal רֵעֵהוּ הָעֲדֻלָּמִי to retrieve the items he deposited by Tamar.

רֵעֵהוּ הָעֲדֻלָּמִי doesn't find her and returns to Yehuda empty-handed.

The Torah informs us in verses 22-23:

וַיָּשָׁב אֶל יְהוּדָה וַיֹּאמֶר לֹא מְצָאתִיהָ וְגַם אַנְשֵׁי הַמָּקוֹם אָמְרוּ לֹא הָיְתָה בָזֶה קְדֵשָׁה: וַיֹּאמֶר יְהוּדָה תִּקַּח לָהּ פֶּן נִהְיֶה לָבוּז הִנֵּה שָׁלַחְתִּי הַגְּדִי הַזֶּה וְאַתָּה לֹא מְצָאתָהּ: ‏

He returns to Yehuda and informs him saying "I didn't find her and the locals claimed there was not a harlot there". To which Yehuda answers saying "Let her keep it, lest we be ridiculed, behold I sent the kid and you didn't find her".

What do the words and you didn't find her add? We already were informed about that in verse 20 (Yehuda sent the kid with his pal רֵעֵהוּ הָעֲדֻלָּמִי to take the deposit from the lady, and he didn't find her - וַיִּשְׁלַח יְהוּדָה אֶת גְּדִי עִזִּים בְּיַד רֵעֵהוּ הָעֲדֻלָּמִי לָקַחַת הָעֵרָבוֹן מִיַּד הָאִשָּׁה וְלֹא מְצָאָהּ) and again in verse 22 - he returned to Yehuda saying I didn't find her - וַיָּשָׁב אֶל יְהוּדָה וַיֹּאמֶר לֹא מְצָאתִיהָ.

Q: What does this 3rd instance "and you didn't find her" add to our understanding or to Yehuda's response?

(It's hard to say that Yehuda was simply venting against רֵעֵהוּ הָעֲדֻלָּמִי.)

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    It's hard to say that Yehuda was simply venting against רֵעֵהוּ הָעֲדֻלָּמִי. Why not? He was in very trying circumstances. | Do you mean that even if a commentator gives that explanation, that that wouldn't be an acceptable answer?
    – mevaqesh
    Dec 4, 2017 at 17:03
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    "the locals claimed she was not a harlot" That doesn't seem like a correct translation. More like "the locals claimed there was not a harlot there".
    – Double AA ♦
    Dec 4, 2017 at 17:27
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    I think there's a nuance in the conversation, here. Perhaps, the translation is "sequential". I.e., "First I tried to find her. I couldn't, so I asked the people of the town and they said that there was no harlot in this town. Despite what they told me, (I.e., just because the towns people didn't know about her, doesn't mean she's not around.) I looked again, but still didn't find her." I know that the friend doesn't say that second part. But, I think that's what Yehuda is implying, i.e., despite what the townsfolk told you that she didn't exist, you looked but still didn't find her.
    – DanF
    Dec 4, 2017 at 18:27

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Siforno and Ibn Ezra mention different comments.

Siforno says that this comment is a way of Yehuda stating that he didn't lie about his thinking. I think this means that when he first sent his friend to find the harlot, he might have skeptical about the whole thing, and then when he asks the towns folk, they say that there was no harlot that ever existed there. So, as I stated in my comment, above, it seem that the friend himself searched for her, at least prior to asking about it, and the fact that he didn't find her, either may be proof (at least, according to Yehuda's thinking) that he didn't make up this story.

Ibn Ezra says that the fact that you didn't find her is a sign that she should keep the deposit that Yehuda left her.

ספורנו הנה שלחתי. ולא שקרתי באמונתי: ‏

אבן עזרא תקח לה. עזוב אותה ותקח הערבון: פן נהיה לבוז. ללעג שנתתי חותם ופתיל ומטה ערבון על דבר קל כזה: ואני הנה שלחתי את הגדי הזה ואתה לא מצאתה. וזה אות כי תקח לה הערבון: ‏

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  • I added the original, to make it easier to understand.
    – Danny Schoemann
    Dec 5, 2017 at 10:52
  • BTW: The שפתי חכמים seems to go along the lines of the Ibn Ezra - ה) רצונו לפרש מה שכתוב הנה שלחתי מה טעם הוא אשלמעלה, ומפרש דהכי קאמר א"ת שהרי מוכרח אני לכך שהרי אמרתי שאשלח לה גדי עזים כי מה עלי וכו' הנה שלחתי וגו', והוכרח להוסיף כי מה עלי לעשות קודם הנה שלחתי, מפני שבזולת זה אין טעם דביקות המאמר תקח לה, למאמר הנה שלחתי וק"ל
    – Danny Schoemann
    Dec 5, 2017 at 10:56
  • I saw Siftei Chachamim, but as I don't understand what he's stating, I didn't use it. If you could summarize his point (I understand most of the Hebrew words, but, I'm still not understanding his point) in English, I suggest that you edit this into the answer. I also think that my comment, above, regarding the sequence is still a valid interpretation, but I don't really see any commentary using that idea.
    – DanF
    Dec 5, 2017 at 15:44
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    I'm wary of fiddling with the sequence of verses - especially within the same "conversation"... I'll try to find time to deal with the Siftei Chachamim.
    – Danny Schoemann
    Dec 6, 2017 at 10:34

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