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There must have been 1000's of Jewish women flaunting themselves at Shimshon. Why did he choose somebody else? or was this not the case? I want to give Shimshon the benefit of the doubt because he was considered to be a tzadik. and say, maybe the Jewish women took no interest in him? it makes no sense that out of all the Jewish women in that time he would find none that would meet his desires unless of course they did not desire him back in return?

This is a thought that has continued to return to me over and over again.

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    The only reason shimshon married a non Jew was the infiltrate the Phillistines. He didn’t it completely l’shem Shamayim. The only way he could attack the phillistines without the Jews getting caught in the crossfire was to become a rebel in the Jewish community by marrying out. Thus the Jews would excommunicate him so to speak and the phillistines would realize he’s not working for them
    – Curious Yid
    Jun 25 at 19:34
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    @CuriousYid Shimshon did not "marry out" in the colloquial usage of the phrase, as he did NOT marry any non-Jewish women. Maimonides (Issurei Biah, 13:16) posits that all of Shimshon's wives converted prior to marriage. This is also the position of the Radak (Shoftim, 14:4).
    – IsraelReader
    Jun 25 at 22:25

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Shimshon's parents asked a very similar question:

(יד:ג) וַיֹּאמֶר לוֹ אָבִיו וְאִמּוֹ הַאֵין בִּבְנוֹת אַחֶיךָ וּבְכׇל עַמִּי אִשָּׁה כִּי אַתָּה הוֹלֵךְ לָקַחַת אִשָּׁה מִפְּלִשְׁתִּים הָעֲרֵלִים וַיֹּאמֶר שִׁמְשׁוֹן אֶל אָבִיו אוֹתָהּ קַח לִי כִּי הִיא יָשְׁרָה בְעֵינָי

And we readers are immediately given an answer to the question as an aside:

(יד:ד) וְאָבִיו וְאִמּוֹ לֹא יָדְעוּ כִּי מֵה' הִיא כִּי תֹאֲנָה הוּא מְבַקֵּשׁ מִפְּלִשְׁתִּים וּבָעֵת הַהִיא פְּלִשְׁתִּים מֹשְׁלִים בְּיִשְׂרָאֵל

There are multiple meforshim (see Metzudos and Malbim) who indicate that G-d chose such a way to infiltrate the Plishtim since they would assume Shimshon would be fighting them as a personal matter and not as a national issue and as such would not generate a full military response.

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  • Care to give a translation of those texts, or at least the verse references?
    – curiousdannii
    Jun 26 at 5:52
  • His father and mother said to him: isn't there among the daughters of your relatives, or all my people, a wife? That you go to take a wife from the uncircumcised Philistines? Samson said to his father -- "take HER for me, as she is proper in my eyes." His father and mother didn't know that this was from G-d, as he was seeking an excuse from the Philistines, as at that time, the Philistines were ruling over Israel.
    – Shalom
    Jun 26 at 8:49

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