Should a Girl Pursue a Guy or Wait for Him?

“Should a girl pursue a guy if she sees godly qualities? Or should she wait for a guy to pursue her?”

This is a great question and it was submitted to our “Anonymous Question Box” that I put out every dating series. While the traditional codes of chivalry would seem to dictate that a woman should wait for a man to pursue her, we have an example in Scriptures of a virtuous woman pursuing a godly man. Let’s look at Ruth 3 as we consider the answer to the question above.

The chapter opens with Naomi, Ruth’s mother-in-law, scheming of a way to get Boaz to notice the bigger picture. We have seen in chapter 2 that Boaz has noticed Ruth and found her to be a woman of character and he respected her a lot. They seem to even have had a date night and he continued to provide and protect Ruth. But then Boaz drops the ball, nothing happens.

We are not immediately told why Boaz didn’t do anything to further the relationship, but Ruth, with Naomi’s advice, sees fit to bring the issue directly to Boaz. So Naomi tells Ruth to get cleaned up, put some perfume on and change her clothes from that of a mourner to clothes that shows the time of mourning are over. Remember, that in chapter 1 we see that Ruth’s first husband has died.

Here is the plan, Ruth is to go to the threshing floor of Boaz at night, right after Boaz lies down to sleep, and uncover his feet and lay at his feet. Naomi told Ruth that Boaz would tell her what to do next.

What?! Right?! How many of you would think this was a good idea? Haha yeah, talk about creepy.

There doesn’t seem to be any cultural equivalent to this. Ruth was probably thinking,” can’t I just Snapchat him?” Back in Moab they would have just “swiped right” and everything would be cool. But she wasn’t in Moab anymore.

Ruth told Naomi that she would do whatever she was told to do. Think about it, Ruth was willing to risk an awful lot in this scenario. What kind of things do you think she was risking?

Security, provisions, reputation, honor, friendship, to name a few. Boaz had made provisions for her to glean in his fields, if he rejected her, would he take that provision away. She had already lost a husband and moved to a foreign land, could she bare another insult if rejected. What would the towns people say? So many other thoughts could’ve prevented her from risking it, but she did.

The night finally came and Boaz was in a good mood as he lay down on the threshing floor to protect his harvest. Ruth crept in, uncovered his feet and lay down at his feet. We are not told what startled Boaz, I think it was cold feet, but he awoke and found Ruth at his feet.

I can’t imagine Ruth would have been comfortable enough to fall asleep, probably laying their anxiously thinking about the worst possible outcomes of this ridiculous endeavor. So she was ready when he asked, “Who are you?” She replied, “your servant Ruth. Spread your wings over your servant for you are a redeemer!”

Let me interpret, “I am Ruth, will you marry me and fulfill the duty of the kinsman redeemer?”

No holding back, no veiled innuendo, just straight talk. Now a Kinsman Redeemer comes from the Law in Deuteronomy 25 and Leviticus 25. When a family loses their land or a widow loses her husband, the nearest relative could redeem them. It’s more then just a marriage, it is inheriting all that was Elimelech’s responsibilities.

If Boaz would accept this proposal, he would gain all of Elimelech’s land, property, gain Ruth as a wife and agree to care for Naomi. Only a relative could be the kinsman redeemer.

Boaz is humbled and honored by her gesture and blesses Ruth. We learn a lot about Boaz in the next couple of phrases. “You have made this last kindness greater than the first in that you have not gone after young men, whether rich or poor.”

The first kindness was when Ruth left Moab and vowed to commit to leave and cleave to Naomi. Here Boaz is recognizing another sacrifice Ruth was making, that instead of just marrying anyone, she was willing to seek a kinsman redeemer that would not only secure her but also Naomi. Ruth’s options were greatly reduced when she agreed to it.

Boaz basically is saying that he didn’t think Ruth would have even considered him. She could have had a younger man, a rich man or anyone. His own insecurities prevented him from pursuing Ruth.

In the dating world, our insecurities can really damage the success of our relationships. It is so important that we develop a healthy understanding of who we are in Christ that will give us confidence to be ourselves. God has specially made you and has a plan for you, never doubt His love for you and the provisions He has in store. Especially learn to take your sins to the cross and allow the power of forgiveness to heal you. Your past mistakes don’t have to define your future.

Boaz promises to do as she asks, but reveals to Ruth that there is another redeemer, a closer relative. Now it get’s really scary! Ruth has met Boaz, seen what kind of man he is and is attracted to him. However, she has asked to be redeemed and the closest relative can now claim that right. She doesn’t know this other man.

Boaz concludes the chapter by giving Ruth a gift of 6 measures of barley, a sign to Ruth and Naomi that Boaz intends to fulfill this duty. He promises that very next morning to find out what the other relative thinks on this.

We learn a lot from Ruth and Boaz in this story. The importance of preparation and getting ready to meet someone, being vulnerable and willing to risk a lot for something we want, dealing with insecurities and being intention in our pursuits.

We also learn, that even godly established men have insecurities and may be oblivious to the potential romance in front of them. Ruth could have waited on Boaz and he may never have pursued her, or even realized that she was interested in him. He was older and had a lot or responsibilities.

So can a woman pursue a guy? Yes, I believe Ruth demonstrates that a godly woman can indeed pursue a guy. But she has to be willing to risk. He may be oblivious, or insecure and therefore needs someone to make her feelings obvious. However, he may not be interested and that is why he hasn’t pursued.

That is why working through insecurities are so important. If take the risk, you might be rejected, but that doesn’t mean God rejects you. Learn from Ruth, have a godly mentor and wait patiently on God. With any risk comes the possibility of being disappointed, but there is also the possibility of gain. The choice is up to you.

As a disclaimer, I think that young men need to step up to the plate and pursue the girl. It can be scary, rejection isn't easy, but it is important for boys to learn to be men and be godly leaders. Even though Ruth made the proposal, once Boaz realized what was going on, he began the steps to pursue her. 

Ladies, if you are pursuing a guy and he never pursues you back, it's time to move on. You deserve to be with a guy who will pursue you and love you the way Christ loves the Church. Christ sacrificed for the Church, He pursed the Church and He demonstrated His love for the Church. Wait on God to find a man who will love you the way Christ does.