A Midnight Encounter
The word "security" in verse 1 is correctly rendered "rest" in the King James Version. It is describing the "rest" found in marriage (see 1:9), that is, "settling down"—typical of the "rest" of God's coming Kingdom (see Hebrews 3-4), wherein the glorified Church will be married to Jesus Christ (compare Ephesians 5:22-23 Ephesians 5:22-23  Wives, submit yourselves to your own husbands, as to the Lord.
 For the husband is the head of the wife, even as Christ is the head of the church: and he is the savior of the body.
American King James Version×; Revelation 19:7 Revelation 19:7Let us be glad and rejoice, and give honor to him: for the marriage of the Lamb is come, and his wife has made herself ready.
American King James Version×).
Naomi remarks again on the fact that Boaz is a close relative—a kinsman-redeemer (Ruth 1:2 Ruth 1:2And the name of the man was Elimelech, and the name of his wife Naomi, and the name of his two sons Mahlon and Chilion, Ephrathites of Bethlehemjudah. And they came into the country of Moab, and continued there.
American King James Version×). "The Hebrew word refers to a relative who acted as a protector or guarantor of the family rights. He could be called upon to perform a number of duties (1) to buy back property that the family had sold; (2) to provide an heir for a deceased brother by marrying that brother's wife and producing a child with her [evidently "brother" being understood as a more encompassing family relation than just a literal brother]; (3) to buy back a family member who had been sold into slavery due to poverty; and (4) to avenge a relative who had been murdered by killing the murderer. The Scripture calls God the Redeemer or the 'close relative' of Israel (Is. 60:16), and Jesus the Redeemer of all believers (1 Peter 1:18 1 Peter 1:18For as much as you know that you were not redeemed with corruptible things, as silver and gold, from your vain conversation received by tradition from your fathers;
American King James Version×, 19)" ("Wordfocus: Close Relative," Nelson Study Bible, p. 446).
Indeed, as briefly mentioned earlier, "the concept of the kinsman-redeemer or goel (3:9, 'close relative') is an important portrayal of the work of Christ. The goel must (1) be related by blood to those he redeems [and Christ came in human flesh] (Deuteronomy 25:5, 7-10; John 1:14 John 1:14And the Word was made flesh, and dwelled among us, (and we beheld his glory, the glory as of the only begotten of the Father,) full of grace and truth.
American King James Version×; Romans 1:3; Philipians 2:5-8; Hebrews 2:14, 15); (2) be able to pay the price of redemption [as Christ was able through His blood] (2:1; 1 Peter 1:18, 19); (3) be willing to redeem [as Christ was willing] (3:11; Matthew 20:28; John 10:15 John 10:15As the Father knows me, even so know I the Father: and I lay down my life for the sheep.
American King James Version×, 18; Hebrews 10:7 Hebrews 10:7Then said I, See, I come (in the volume of the book it is written of me,) to do your will, O God.
American King James Version×); (4) be free himself [from whatever caused the need for redemption, i.e., the redeemer cannot redeem Himself] (Christ was free from the curse of sin). The word goel...[thus] presents a clear picture of the mediating work of Christ" (New Open Bible, introductory notes on Ruth). It is also of interest that a Christian needs to agree to God's way in order to receive the blessing. A Christian needs to want salvation. Ruth wanted Boaz to marry her and she agreed to the system.
Naomi decides it's finally time to act. The end of harvest always meant celebration and feasting in ancient societies. Perhaps she thought Boaz would be most receptive to any appeals or proposals at such a happy occasion. She tells Ruth to wash, put on perfume and dress in nice clothes and then sends her down to the festivities, but not to approach him during them (Ruth 3:3 Ruth 3:3Wash yourself therefore, and anoint you, and put your raiment on you, and get you down to the floor: but make not yourself known to the man, until he shall have done eating and drinking.
American King James Version×). Rather, Naomi instructs Ruth to follow Boaz and, after he fell asleep, uncover his feet and lie down at them (verse 4). This seems rather strange to us today, but it appears to have been more common and understood in the culture of the time. Today some view it as a sexual advance, accusing Ruth (and Naomi for suggesting it) of immorality. But that is rather unlikely, as we will see.
Boaz goes to sleep out in the open (verse 7). With most of the harvest at the threshing floor, it was not uncommon for the owner or a trusted servant to sleep near the pile of grain to guard against theft. He wakes at midnight, startled to find Ruth at his feet. She says to him, "Spread therefore thy skirt over thine handmaid: for thou art a near kinsman" (verse 9, KJV). First of all, we should notice that this is a humble petition, as she calls herself his handmaiden—his servant. This may explain her presence at his feet, the position of a lowly petitioner. Furthermore, in the NIV the expression "thy skirt" is rendered "the corner of your garment." Some see this as a reference to a cloak or outer robe that was being used as a blanket (see C.F. Keil and F. Delitzsch, Commentary on the Old Testament).
"Boaz probably slept upon a mat or skin; Ruth lay crosswise at his feet—a position in which Eastern servants frequently sleep in the same chamber or tent with their master; and if they want a covering, custom allows them that benefit from part of the covering on their master's bed. Resting, as the Orientals [i.e., Middle Easterners] do at night, in the same clothes they wear during the day, there was no indelicacy in a stranger, or even a woman, putting the extremity of this cover over her" (Jamieson, Fausset & Brown Commentary, note on verse 9).
In the plural the Hebrew term translated "skirt" is usually understood to mean wings, and thus some translations, such as the New King James Version, translate it here as "wing." God used this terminology in describing His taking of Israel as His wife: "Behold, thy time was the time of love; and I spread my skirt over thee, and covered thy nakedness: yea, I sware unto thee, and entered into a covenant with thee, saith the Lord God, and thou becamest mine" (Ezekiel 16:8 Ezekiel 16:8Now when I passed by you, and looked on you, behold, your time was the time of love; and I spread my skirt over you, and covered your nakedness: yes, I swore to you, and entered into a covenant with you, said the Lord GOD, and you became mine.
American King James Version×, KJV). In the New King James Version, the key phrase here is translated "so I spread My wing over you." Clearly, Ruth's intent was a proposal of marriage—that she come under the wing or cloak of a husband's protection, namely Boaz's.
What is also rather significant in this regard is that Boaz had earlier spoken to her of "the Lord God of Israel, under whose wings you have come for refuge" (Ruth 2:12 Ruth 2:12The LORD recompense your work, and a full reward be given you of the LORD God of Israel, under whose wings you are come to trust.
American King James Version×)—here using the plural form of the same Hebrew word. Yet he had not sent her on her way to be protected by God somewhere else. Rather, to a great degree, he took on the duty of providing and caring for her himself.
Since this true story illustrates the relationship between Christ and the Church, there might seem to be a breakdown in the typology. Jesus said, "You did not choose Me, but I chose you..." (John 15:16 John 15:16You have not chosen me, but I have chosen you, and ordained you, that you should go and bring forth fruit, and that your fruit should remain: that whatever you shall ask of the Father in my name, he may give it you.
American King James Version×). This is after God the Father selects those who are to be part of the bride for His Son (John 6:44 John 6:44No man can come to me, except the Father which has sent me draw him: and I will raise him up at the last day.
American King James Version×). But consider that Ruth did not initiate the relationship. Boaz had already taken a keen interest in her and had shown obvious favor toward her. Indeed, it is likely that he very much wanted to be her husband. But we see that he is an older man who expected Ruth to marry someone much younger. The wise Naomi recognized Boaz's feelings for what they were. She may have known that Boaz was a conservative man who lacked romantic assertiveness. Naomi decided it was time for Ruth to show some initiative as a response to Boaz's interest. Likewise, after being called by God we are to exercise initiative in seeking Him. "Draw near to God and He will draw near to you" (James 4:8 James 4:8Draw near to God, and he will draw near to you. Cleanse your hands, you sinners; and purify your hearts, you double minded.
American King James Version×).
Boaz is deeply touched. And he is immensely impressed with Ruth's great "kindness" (verse 10)—the Hebrew word here, hesed, meaning "loyal love" or "covenant faithfulness." Not only had she stuck by Naomi, but now she was seeking to fulfill the obligation of preserving the lineage and inheritance of her deceased husband, which would restore the family line of Elimelech and ensure that Naomi was well provided for.
Boaz's response really helps us to see that no sexual impropriety was occurring. If Ruth had been doing something immoral, his first words would surely not be to bless her in God's name for her faithfulness and moral virtue (verses 10-11). His telling her to sleep there until morning (verse 13) was most likely to ensure her protection. It would not have been safe for her to walk back to town in the middle of the night, when she might have been accosted—just before dawn would be safer, when no one was awake. It is true that, in verse 14, Boaz does not want anyone to know she'd been there. But that doesn't mean anything wrong had transpired. Perhaps he just didn't want the encounter to be misconstrued and Ruth's reputation brought into question. Or maybe he just didn't want his intent of marriage to become public until he was able to sort out the situation with the other relative he mentions. For Boaz, we find out, was not the nearest kin (verse 12).
In the morning, Boaz sends Ruth home with a gift of grain—6 unspecified measures (verse 15). The New King James has ephahs but that would be around 187 pounds, pretty difficult for her to carry in her shawl. Perhaps Boaz just used a scoop and dumped six full scoops into her shawl. This gift may have been a pledge of his intentions to marry her if possible. At the end of the chapter, Naomi tells Ruth to, in modern parlance, "sit tight and wait and see." Naomi is confident that Boaz, who has repeatedly demonstrated uprightness and compassion toward them, will have the matter resolved before the day is over (see verse 18).