What does Ruth 3:10 mean?
ESV: And he said, “May you be blessed by the LORD, my daughter. You have made this last kindness greater than the first in that you have not gone after young men, whether poor or rich.
NIV: The LORD bless you, my daughter,' he replied. 'This kindness is greater than that which you showed earlier: You have not run after the younger men, whether rich or poor.
NASB: Then he said, 'May you be blessed of the Lord, my daughter. You have shown your last kindness to be better than the first, by not going after young men, whether poor or rich.
CSB: Then he said, "May the Lord bless you, my daughter. You have shown more kindness now than before, because you have not pursued younger men, whether rich or poor.
NLT: The Lord bless you, my daughter!' Boaz exclaimed. 'You are showing even more family loyalty now than you did before, for you have not gone after a younger man, whether rich or poor.
KJV: And he said, Blessed be thou of the LORD, my daughter: for thou hast shewed more kindness in the latter end than at the beginning, inasmuch as thou followedst not young men, whether poor or rich.
Verse Commentary:
On what is likely the final night of a prosperous harvest, as the workers sleep on the threshing floor, protecting the newly winnowed grain, Boaz awakens to see a figure lying at his feet. It's Ruth, and she has a proposition (Ruth 3:1–9). Boaz is a good man—and rich. He's also related to Ruth's late father-in-law. That means Boaz can buy Elimelech's land, thus providing for his widow's needs (Leviticus 25:25–28, 47–49). In addition, Ruth challenges Boaz to marry her and provide an heir for Naomi who will re-inherit the land to keep it in Elimelech's family (Deuteronomy 25:5–6).

Naomi told Ruth to proposition Boaz for Ruth's sake—so she would have a good husband and find "rest" (Ruth 3:1). Ruth has spent two months gleaning from Boaz's fields. At least half of Boaz's harvesters are young men—closer to Ruth's age. She could have presented herself as available to any of them. She didn't, however. Only the older Boaz can give her what she really wants.

Many Bible scholars have interpreted Boaz's words to mean he appreciates that Ruth, a young vibrant woman, has chosen him, an old codger, as if he needed his ego stroked. That's not the "kindness" Boaz is referring to. The first "kindness" was when Ruth left her family and her homeland and traveled from Moab to Bethlehem to take care of Naomi—something Boaz has already praised her for (Ruth 2:11–12). Now, Ruth goes above even that kindness. She could have found herself a rich young man or a poor man she loved; either would have been around for a long time and given her lots of babies. Instead, she wants to marry a relative of her in-laws. She chooses family loyalty over her own self interests.

Levirate marriages are part of the Mosaic law. If a man dies with no heirs, his brother is to marry his widow and have a son in the dead man's name. The son will receive the inheritance of the dead man. This is the story of Tamar (Genesis 38) and one part of the Sadducees' argument against the resurrection of the dead (Mark 12:18–27). Naomi is bitter not just for herself, but because when her sons died, she failed in providing Elimelech an heir (Ruth 1:1–5, 20–21).

Boaz doesn't meet the literal interpretation of the law: he is neither Elimelech's nor Ruth's late husband's brother; he's a more distant relation. But he sees that Ruth is willing to give up her life and her future for Naomi's honor. In response to her continued kindness, the least he can do is marry this young, honorable, loyal, hard-working widow!

"Gone after" often describes either illicit sexual relations (Proverbs 7:22; Hosea 2:7) or marriage (Genesis 24:5; 1 Samuel 25:42). Considering Boaz's praise of Ruth's character, it's obvious he means marriage.
Verse Context:
In Ruth 3:10–15, Boaz presents his plan to make Ruth's plan come to fruition. She has asked him to be Naomi's kinsman-redeemer, to buy Naomi's land and provide for her needs. Ruth has also proposed marriage and asked Boaz to give Naomi an heir who will inherit the land. Boaz is humbled by Ruth's dedication to her mother-in-law, but there's a problem—he is not the closest relative. He has to offer the plan to another man. If that man refuses, he will do everything Ruth says.
Chapter Summary:
In Ruth 3, Naomi schemes to find Ruth a good husband, as was always her hope (Ruth 1:9). She tells Ruth how to propose to Boaz. When Boaz has fallen asleep after a long and joyful day of winnowing grain, Ruth is to gently awaken him and make her proposal. Ruth goes beyond Naomi's instruction, however. Boaz understands that Ruth expects him to buy Naomi's land and give her an heir to re-inherit it. He praises Ruth for her devotion to her mother-in-law, but there is another relative who is closer. In the next chapter, Boaz dispenses with his rival and marries Ruth.
Chapter Context:
Ruth 3 is the wind-up to the climax of the story. Ruth and Naomi returned to Bethlehem from Moab two months prior. Boaz, a relative of Naomi's late husband, has allowed Ruth to harvest enough grain to last the women a year (Ruth 1—2). Now that their physical needs are addressed, Naomi wants Ruth married to Boaz. Ruth wants Boaz to provide an heir for Naomi. Boaz is again impressed with Ruth's self-sacrifice and agrees (Ruth 3). After negotiating with a closer relative, Boaz marries Ruth and gives Naomi a son. That son becomes King David's grandfather (Ruth 4).
Book Summary:
Though set in a time of violence and tragedy, the book of Ruth tells one of Scripture’s most uplifting stories. Naomi, an Israelite, leaves her home during a famine. While away, in Moab, her husband and sons die. Naomi convinces one of her Moabite daughters-in-law to leave her and seek a new life. The other, Ruth, refuses, declaring her love and loyalty to Naomi. When the pair return to Israel, they encounter Boaz. This man is both kind and moral; his treatment of Ruth secures Naomi’s future and becomes part of king David’s ancestry.
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