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I know the Talmud describes how the fifteenth day of the month of Av (Tu b'Av) was a day of ... I'd say "matchmaking", but I think "marriage-minded-singles-meeting" is more like it:

אמר רבן שמעון בן גמליאל לא היו ימים טובים לישראל כחמשה עשר באב וכיוה"כ שבהן בנות ירושלים יוצאות ... וחולות בכרמים ומה היו אומרות בחור שא נא עיניך וראה מה אתה בורר לך אל תתן עיניך בנוי תן עיניך במשפחה (משלי לא) שקר החן והבל היופי אשה יראת ה' היא תתהלל ... תנא מי שאין לו אשה נפנה לשם

(Taanis 31a, and related final mishna)

And I know that today, there's no shortage of institutions hosting singles events, shabbatons, etc. around Tu B'Av.

But what about the 1800 years between then and now? Do we have sources (rabbinic or general historic) as to how Tu B'Av was observed for marriage-minded singles in different times, places, and cultures?

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It was not,as Lag Baomer and fires is a recent thing and so is Tashlich a more recent thing. –  SimchasTorah Jul 26 '10 at 22:11
    
YS, LagBaomer bonfires and Tashlich are not in the Talmud, but everyone does them. Here's one that was in the Talmud, but then nobody did it? I suspect in communities with arranged marriages, why would this date (pun intended) be different than any other. Also the Mishna discussed pre-Destruction Jerusalem; was it limited to Jerusalem? –  Shalom Jul 26 '10 at 22:59
    
בנות ירושלים does seem to indicate it was limited to Jerusalem Shlomo –  Ishyehudi Jul 27 '10 at 20:50
    
there is some info on the wiki: he.wikipedia.org/wiki/… the links there could be useful –  jutky Oct 11 '10 at 22:47
    
It would make sense that this holiday was not observed from the time that Jerusalem was destroyed until 1967. But the real point of my comment is that there are many holidays and fast days mentioned in the talmud which are not observed today. –  avi Feb 10 '12 at 9:53

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For a great resource on various events that happened on Tu B'Av throughout history, check out Larry Domnitch's The Jewish Holidays: A Journey through History. Regarding singles events, he cites the fairs in 16-17th century Poland. On page 113-114, he writes:

In those days, matches were often made at fairs where the multitudes gathered. In the book Yeven Metzula by Rabbi Nathan Nata Hanover, the author describes how thousands converged upon the fair in Poland in the years prior to the Chmielnicki massacres (1648-1649). The open fairs of the summer were held on the seaside villages of Zaslow and Yerislav and attracted great numbers of people. The fair was a place of socializing, conducting business, and relaxation. It served as a brief respite from the difficulties of life.

Tu B'Av marked the end of the summer sessions in the yeshivas in Poland and thousands of students would converge upon the fair with their instructors. There, they studied with students from other yeshivas.

Naturally the fair was an ideal place for networking and the arrangement of marriages. Rabbi Hanover wrote, "Whoever had a son or daughter of marriageable age journeyed to the fair, and there arranged a match. There was ample opportunity for everyone to find their type and suit...hundreds and sometimes thousands of such matches would be arranged at the fair." [...]

The fairs in Poland were a substitute for the open fields in biblical times. The times, circumstances, and locations in which marriages were arranged have frequently changed and they continue to change. Diverse situations, however, offer the same opportunities for those in search of their of their bashert (destined one) and allow for the continuity of the Jewish people.

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