On this day, the young women of Jerusalem would go out dressed in their white finery and dance in vineyards, in a courtship ritual that led to marriage.
Three lessons from Tu B’Av come to mind with regard to shidduchim specifically.
[a] Who are you – The Mishna tells us, the two happiest days for the Jewish People are Tu B’Av and Yom Kippur.
Yom Kippur, is one of the most intense days of the year. We spend 25 hours fasting and praying to Hashem to forgive our transgressions and allow us another year to fulfill our mission in this world, be with family and fulfill our potential. As hungry and exhausted as we may be, by the end of Yom Kippur, we feel cleansed, liberated, purified and exhilarating. We have made an internal introspection and are committed to bettering our actions throughout the coming year.
Tu B’Av has to do with finding clarity in who you want to marry. This involves with finding clarity within yourself: who you are, what are your values and motivators in life, how you let yourself down, and how you psych yourself up. Self-knowledge is very powerful, and very necessary for finding your partner in life. This is why so many people unfortunately have such a hard time finding the right one. You can’t know what you want if you don’t first truly know who you are.
[b] Who do you want to marry – Our sages tell us that the women would swap dresses with each other before they started dancing. Aside from being a fun opportunity to temporarily expand their wardrobe inexpensively, it also prevented their potential suitors from knowing each woman’s socio-economic status. If a woman is wearing her friend’s dress, then the groom-in-waiting couldn’t make those assumptions about her. This way he could focus all his attention on getting to know her as a person without any other superficial factors side tracking him.
[c] Running around in circles – Tu B’Av is the time when female and male become one. Like a circle and line combined each feeding off each other to complement each other. A circle has no beginning and no end. “The end is entwined in the beginning and the beginning in the end” (Sefer Yetzirah). It is totally encompassing and inclusive. The chosson and kallah do not remain independent, but on the contrary, are unified as one whole.
Rabbi Yitzchok Groner z”l (Melbourne Australia) pointed out on numerous occasions that Tu B’Av refers to the 15th letter of the Aleph-Bet; which is the letter “ס” (Samech).
During the chuppah and wedding ceremony, the circle is emphasized a number of times.
When the kallah enters the chuppah, she circles her chosson 7 times.
[ii] The chosson places the ring (a circle) on her finger in acquiring her for matrimony.
[iii] The kesubah is rolled and handed to the kallah like a scroll.
[iv] When the dancing ensues at the wedding, men and women form 2 separate circles.
In the merit of Tu B’Av, may all those seeking their bashert find theirs immediately in order to build a binyan adei ad – an everlasting and eternal edifice.