Throughout my decade as an unmarried man in the church (from age 19 to 29), I learned a lot about godly single manhood. One lesson that proved somewhat elusive, however, was how to relate to single women.

I no doubt grew some in that area. My Christian twenties avoided much of the foolishness from my non-Christian teens (thank God). I enjoyed some healthy relationships with sisters in Christ — relationships marked by clarity, mutual respect, and the right kind of friendship. But I often felt adrift. I sometimes kept a cool distance when I should have spoken a kind word. I sometimes drew close when I should have maintained some space. I guessed and second-guessed. I wounded and was wounded.

The spiritual sisters in a single man’s life are an incalculable gift. In fact, among the “hundredfold” blessings Jesus promises to those who follow him, he specifically mentions not only “houses and brothers and . . . mothers and children and lands,” but “sisters” (Mark 10:29–30). Jesus gives these sisters to single men (and single men to these sisters) as friends and fellow pilgrims on the path from grace to glory.

But relating well to sisters in Christ takes care. It takes love and wisdom, humility and counsel, self-control and sensitivity to the Spirit. So, how might a single man mature in his relationships with single women? How might he become more of the brother Jesus calls him to be?

Our Call to Honor

If we were to pick one word to capture a single man’s overall posture toward the women in his life, it may be honor. The apostle Peter names honor as a central part of a husband’s calling toward his wife (1 Peter 3:7), but such honor doesn’t begin when a man becomes a husband. It begins when he becomes a brother. Built into godly brotherhood is an impulse to protect and respect, to cherish and keep — to honor.

“Built into godly brotherhood is an impulse to protect and respect, to cherish and keep — to honor.”

Consider, for example, two sterling models of single brotherhood in the New Testament: our Lord Jesus and his apostle Paul. Jesus was not ashamed to call his female disciples “sisters” (Matthew 12:50). Though he chose men as his twelve apostles, he called many women to follow him as well, sometimes even living off their financial provision (Luke 8:1–3). We get a good sense of how women felt around Jesus in Luke 10:39, where Mary sits lovingly at her brother-Lord’s feet — safe, at home, honored.

Paul, like his Lord, did not hesitate to honor the honorable sisters in his life, and to do so publicly. Of the twenty-nine people he greets in Romans 16, nine are women. And of these women, “our sister Phoebe” receives his first commendation as the carrier of Romans and Paul’s own patron (Romans 16:1–2). In Philippians also, as Paul mentions Euodia and Syntyche, he not only calls the women to unity but commends them as sisters “who have labored side by side with me in the gospel” (Philippians 4:3). Paul seemed to set boundaries on his relationships with women — all his traveling companions were men, for example — but within those boundaries, he was eager to honor.

So, if a single man wants to relate to women as Jesus and Paul did, he will learn the art of honoring sisters. He will ask how he might make women feel safe, dignified, and seen. And to that end, he might give his attention to four key postures: purity, clarity, courage, and community.

1. Purity (in the Secret Mind)

When Paul tells the young Timothy how he should relate to the various members of his church, he calls him to treat “younger women as sisters, in all purity” (1 Timothy 5:2). Such purity would shape Timothy’s outward behavior toward women, but only by first shaping his inward character, including the most secret realms of heart and mind.

A godly man knows that impure words and actions both come “out of the abundance of the heart” (Matthew 12:34; 15:19). So, a godly man guards his heart above all else. He knows that if this city is taken, the whole realm falls. If this fountain is polluted, every stream becomes dirty. No matter how much he may seem to honor women on the outside, his honor is hypocrisy as long as he defiles women on the inside. And in all likelihood, inward dishonor will find its way outward in time.

Purity, then, is his pursuit — and purity not just on the margins of heart and mind, but through and through. He opens every window, every door, from closet to cellar to attic, asking God to cleanse the whole house. No pornography is good; no fantasy is better. No fantasy is good; no second glances are better. No second glances are good; no subtle assessments of a woman’s shape are better.

No man (or woman, for that matter) will attain perfect purity here. Perfect purity comes only when we finally see Jesus’s face (1 John 3:2). Until then, grace abounds to every struggler walking in the light. But if we want to honor the women in our lives, we will begin here. We will believe that inward purity, flowing from a lively joy in Jesus, carries pleasures impurity can never give. And so we will say no to lust and keep saying no; we will say yes to Christ and keep saying yes.

2. Clarity (in Word and Deed)

Then, having set his sights on purity, he turns his attention also to clarity. Among our churches’ single women, some likely feel confused about a single brother’s behavior. Does he just like being friends, or does he want more? Would he text so much if he weren’t interested in dating? What should I do if we keep having deep conversations?

On the one hand, such questions are sometimes unavoidable; they arise naturally from the uncertainty of singleness. On the other hand, single men can do much to mark their relationships with clarity. They can speak in ways that avoid flirtation and suggestion. They can act consistently with their intentions. They can bring the blessed air of clarity into a relational setting often fraught with confusion.

“Let each of you look not only to his own interests, but also to the interests of others,” Paul writes (Philippians 2:4). Relationships with single women often tempt a man to look to his own interests. Flirting feels fun. Sharing jokes offers a sense of intimacy. Trading glances touches some deep yearning for closeness. Yet when flirtations and inside jokes and mutual looks happen apart from an intentional pursuit, they can trample a woman’s interests underfoot.

How might a man tell if he’s relating to women with clarity in word and deed? He might ask the following questions:

• Do I find myself showing special attention to any woman? Do I drift to her first in a crowd? Do I instinctively look her way in group conversation? Do I communicate with the kind of depth or frequency that might suggest interest?
• Do I sense any woman giving me special attention? And if so, have I done something to welcome and encourage her interest?

“Rightly built, clear boundaries give space for good things to grow.”

Rightly built, clear boundaries give space for good things to grow. When a sister has no doubt that a man is merely a brother, he can honor her without suspicion, he can do ministry beside her (and others) without suggestion, and he can enjoy conversation without unwisely awakening love.

3. Courage (in Pursuit)

The time comes, of course, when a relationship marked by clarity seems like it could become more. Gradually, a woman grows in a man’s esteem. Their friendship deepens within wise boundaries. He wonders if she could feel the same. How does he honor her now, as his heart turns toward pursuit? In part, by showing courage.

Someone needs to take the first frightening step. Someone needs to initiate the risky conversation, say the bold word, ask the honest question. Someone needs to lead in vulnerability. Why not you? The call for clarity has already taught a man to treat her interests above his own, so why not in pursuit as well?

No doubt, women can also find ways to show courage. Remember Ruth. But in general, the impulse of a godly man to protect the women around him bids him to bare his heart first, knowing full well it may be rejected. “From heaven he came and sought her,” we sing of our Bridegroom. So, in dim reflection of him, go and seek your bride.

To be sure, we should beware of reckless courage. Sometimes, a man pursues a woman who barely knows him and has less than a clue of what’s coming. She has heard him speak only from across the room; she has known him only at a distance. And now, out of nowhere, he’s sharing his soul (and maybe even using the m-word). He tries to pick her up in his car while traveling 60 miles per hour.

But recklessness aside, a godly single man cannot escape courage. She may well disappoint you to your face, but she will in all likelihood respect you. You will have honored her by your pursuit, your clarity, your courage, and the Lord Jesus knows how to heal hearts injured on the road of honor (Psalm 147:3).

4. Community (in All)

Finally, in every part of single brotherhood, lean deeply into your community. Sometimes, purity can feel unattainable. Clarity can feel confusing. Courage can feel hopelessly daunting. But with a community at your side — counseling you with wisdom (Proverbs 12:15), stirring you up “to love and good works” (Hebrews 10:24) — it can all feel suddenly possible.

My colleague Marshall Segal calls community “the third wheel we all need”:

We all need a third wheel — in life and in dating — people who truly know us and love us, and who want what’s best for us, even if it’s not what we want in the moment. (Not Yet Married, 171)

Such people may not be easy to find. And even if we do find them, they may not voluntarily offer the counsel we need to hear. We probably will need to seek and draw it out of them. Go ahead, then, and tell a brother what temptation looks like right now. Ask a married couple to keep an eye on your relationships with single women — and to tell you if you seem flirtatious or standoffish. When the time for courage comes, find strength from the words and prayers of others. And then find comfort if you’re wounded.

No man remains on the path of honor alone. But with the help of brothers, fathers, and mothers — gifts of that hundredfold community Jesus promised — he can learn to love and honor the sisters in his life.