I am working on a discussion guide for the book of Ruth. It may end up being part of a Shavuot Haggadah I hope to write as part of my Mount Olive Press project. Or it may even turn into a stand-alone book.
As I did a little initial reading (Artscroll Mesorah Series on Ruth), I came up with some preliminary questions. With some polish, these could become good discussion starters for a small group experience or study partnership (chevruta) experience with Ruth:
How can David’s line come from Ruth, a Moabite, when Torah says no Moabite or Ammonite for ten generations may enter the assembly?
Was Boaz a legitimate kinsman redeemer according to the Torah’s levirate marriage regulations? Do the Biblical genealogies tell us how Boaz is related? Rabbinic tradition?
Is Boaz as go’el intended to have messianic overtones?
Is there a purpose for this book amid the time of the Judges?
Did Boaz die right after his wedding night?
How does the Ruth story fit into the transcendent story arc of the Bible (the Abrahamic blessing)?
Messianic Jewish Musings 
It is interesting to keep in mind that not only was Boaz’ wife Ruth a gentile convert to Judaism, so was his mother. Boaz was the son Rahab (a gentile woman who helped facilitate the entry of Joshua and the Hebrews into Israel), and Salmon (said to be the first of the Tribe of Judah’s Davidic line to cross the Jordan River into the Promised Land).
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