The Avodah of the Fifteenth of Av

A chossid once asked the Divrei Shmuel of Slonim, zt”l: “Why does the gemara in Taanis 26 state that there were no holidays like the fifteenth of Av and Yom Kippur? Why is the fifteenth of Av compared to Yom Kippur, the holiest day of the year? Also, why isn’t Yom Kippur mentioned first?”
The Rebbe explained, “This is hinting that the days of teshuva begin on the fifteenth of Av and extend all the way to Yom Kippur! As he famous saying goes: Av is an acronym that spells Elul bah, Elul is on its way. Anyone who can arouse themselves to repent during these days of mercy should do so. Anyone who can’t should at least do so by contemplating the merit of their righteous ancestors. This will also work well. However, someone who simply cannot arouse himself to teshuva on the fifteenth of Av should take a different hint from the gemara. It tells us that the custom was that they would ‘borrow clothes one from the other.’ If a person feels uninspired to repent, he should ‘borrow’ inspiration from his friend or teacher who does feel aroused to change. Let such a person ask someone inspired what awakened him until he feels like he is beginning to wake up spiritually and start to do teshuva!”
The Lev Simcha, zt”l, answered differently: “There were no days for the Jewish people that could compare to the fifteenth of Av. The gemara is very clear that people would make matches on that day. So we see that one needs a very special measure of assistance from above to merit to make good shidduchim for oneself and one’s children. We should not take this for granted! Shidduchim are not a simple matter at all!”