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What Happened on that day, and why is it such a segulah for Shidduchim on that day?????
See in the Sefer Hatodah all the reasons in great detail.
Not sure about the shidduchim aspect, but the day is important because in the last year in the midbar, that’s when they knew the gezeirah of everyone dying in the midbar because of the incident with the meraglim, was over
Look at the mishna in taanis לא הי’ יו’ט לישראל it was a day of forgiveness, as the gezera of the meraglim was over in the fortieth year, like yom kippur where the girls would dress up in white.
It is a Mishnah in Masechet Ta’anit, Perek 4, Mishnah 8
אמר רבן שמעון בן גמליאל: לא היו ימים טובים לישראל כחמשה-עשר באב וכיום הכיפורים, שבהן בני ירושלם יוצאין בכלי לבן שא[ו]לים, שלא לבייש את מי שאין לו – כל הכלים טעונים טבילה – ובנות ירושלם יוצאות וחולות בכרמים. ומה היו אומרות: שא נא עיניך, בחור, וראה מה את בורר לך; אל תתן עיניך בנוי תן עיניך במשפחה
Great question. So great that the Gemarah and Medrash actually ponder the same… Sounds exciting… look it up yourself. Anywhere a Gemarah or Medrash can be found. (actually its mentioned more than once in Gemarrah, and numerous times in Medrash!)
The girls of Jerusalem dressed in borrowed white clothing and danced in the vineyards. The bachelors would go there and choose a mate. Shaul Hamelech was too shy to approach a girl so he had to wait until a girl approached him.
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