The Mem

יעשה ה' עמכם חסד כאשר עשיתם
Hashem should do kindness for you as you have done.
The words עמכם and עשיתם conclude with the letter ם which is the masculine form of the word, rather than a ן which would indicate feminine. Why?
The Midrash teaches us that in the merit of Orpah walking forty steps with Na'ami her son Goliath spent forty days threatening the Jews before being killed by Kind Dovid. The forty steps that each of them took are being alluded to with the letter ם (which has the numerical value of 40) that concludes those words. Na'ami had nothing to offer them at this time in her impoverished state, but she was offering her blessing that they should be rewarded by Hashem for their footsteps.

Na'ami Returns

The Megilla describes Na'ami as leaving the land of Moav and setting her sights on her return to the land of Yehudah.
Frequently when people lose their fortunes they leave the places where people know them and travel to places where they are unknown. They are embarrassed to face those who had been below them on the social scale and have now risen above. Na'ami knew that her financial downfall was a result of her family's decision to leave the Land of Israel and go to Moav. Rather than hiding from others, she accepted her punishment and was prepared to face others in her new predicament. 

Judges

In the first verse of Megillas Rus the word ויהי (indicating a calamity) is repeated. Why? The Midrash says that it is to tell us that there were two famines. One a famine of food and one a famine of Torah. In a generation of no Torah, there is a famine. "In the days of the judging of the judges," is a generation in which the judges need to be judged. There is no greater denigration of Torah than that.

Judging

"It was in the days of the judging of the judges and there was a famine in the land."
There is a Midrashic comment:
When God decides to judge the world, who does he judge first? Those who judge the world. They judge the world, and who judges them? God.
When I read this it makes me stop and think how frequently I am judging others and what the consequences are for myself.

ויהי

The Megilla of Rus begins with the word ויהי (It was). The Talmud tells us that the word ויהי always indicates a calamity. By contrast, the word והיה (it will be) always indicates a time of joy. What is the reason for this distinction?
In Hebrew we have a concept called ו' המהפך, this means that when a verb is preceded by the letter ו, the function of the ו is to switch the tense of the verb. A past tense verb becomes future tense, a future verb becomes past. The word יהי is future. It means: it will be. Adding the ו changes it to past tense: it was. The future is full of endless possibilities. It has not yet occurred and there is no telling what it will bring. It is full of hope. Turning the future to past freezes it as being one possibility and negates all the others. This is calamity.
והיה is the opposite. The word היה by itself indicates past tense. Adding the ו changes it to the future. We have taken the past that seemed frozen and stuck in one way, and learned that even the past can be reframed and changed and doesn't have to remain the way we remembered it. This is joy.

The House that Rus Built

Over the next week until Shavuos begins I wanted to share some insights from the Sefer Shoreh Yishai on the Book of Ruth. This commentary was authored by Rav Shlomo Alkabetz. He is most famous for authoring Lecha Dodi and as the brother-in-law of the Ariza"l. His most famous work is on the Book of Esther and in this work he follows the same pattern of Midrashic interpretation as well as some original insights.