Diagnostic Questions for Ministering to Singles


In my present station in life, I have the joy of ministering among women of various life-stages, circumstances, cultures, and geographical locations. Because I’m single, many of these women ask me questions publicly and privately about singleness and ministry among single people. I’m often reminded how important it is that we single people engage in fellowship with men and women in different life-stages and circumstances (and vice versa!). Our whole-body fellowship helps to cultivate empathy for brothers and sisters in Christ who are lonely in marriage, or who have children rebelling against Christ, or who are impoverished, or who battle chronic illness, or . . . the list goes on. We’re family in the Lord Jesus, and this must shape how we talk about singleness among Christians.

Below, I’ve compiled the questions women most often ask me. Pastor, as you are preaching through the Scriptures and thinking about applying the text, you might consider whether your text addresses questions like these. If you dealt with one a week for a year, consider how equipped single people would be! It may also be helpful to discuss select questions with ministry leaders in your church, host a seminar for single people on Christian dating, or write a pastor’s column discussing questions relating to family life in the church.

Two disclaimers. First, many single men may be asking these same questions. I’ve focused on questions from women simply because this reflects my predominant experience. Second, I regularly hear single people say that they don’t like it when others assume all single people are the same. Not all single women, for example, want to be married and/or give birth to children. Not all single women feel insecure about being single. Not all single women think their singleness affects their professional relationships. And so on. Single people aren’t monolithic, and neither are the questions they ask.

So, here are questions some single Christian women ask.

1. Questions relating to identity.

As a single person, do you ever feel that something’s wrong with you? If so, how do you deal with that feeling—is it the sort of thing you ignore, or the sort of thing you talk about with someone else to see if it’s true? Do you feel a sense of shame about being single? Do you wrestle with identity issues because you have a strong personality? (Apparently I have a strong personality.) Have you ever thought it would be best to adjust your personality in order to attract a man who might otherwise be intimidated by you? Why does everyone assume I’m having an identity crisis just because I’m single? Why would God design me as a nurturer (or whatever else) and give me such strong desires to know intimacy in marriage and motherhood and yet withhold that from me? How will I ever experience satisfaction in life with unfulfilled desires and longings this basic to my person?

2. Questions relating to loneliness and loss.

How often do you feel really lonely? What sort of relationships do you cultivate in your life to keep from getting lonely? Am I always going to feel this sad about being single, or are there seasons to it? What does it mean to be “content” in my singleness? Can I be sad and content at the same time? Why are holidays so lonely for me, and should I start making different holiday traditions as a single person so that they’re not so horrible? What do I do when all my friends are married with children, and they only talk about their kids when we get together? Is it important to have friends who are also single? How do you deal with sadness and jealousy when a friend gets engaged/married, or announces she’s pregnant, or talks about her sex life? How am I supposed to “rejoice with those who rejoice” when they get engaged or pregnant, if they don’t “mourn with those who mourn,” like me? How often do you grieve that you might not ever be a mother? Is it okay to grieve something like that preemptively (like in your 20’s and 30’s), and how do you grieve that in a healthy way? How do you handle the fear of being alone in your old age, with no one to care for you?

3. Questions relating to the workplace and “work/life balance.”

What do healthy “boundaries” look like as a single person? What habits do you cultivate as a professional to ensure that you stay spiritually, emotionally, and physically healthy? What do you do when your supervisor takes advantage of your singleness by making you take all the evening meetings, holidays, etc.? (I hear this about supervisors more often from women in full-time occupational ministry.) Do you vacation differently as a single person to be sure you get adequate rest and renewal? Since you’re not married, do you have an accountability partner that makes sure you don’t let work swallow up your life? When my married friends talk about all that they’re juggling, do they not understand that I have to make all major decisions by myself and handle all life’s logistics by myself—and do all this on one income? What do I do when I feel like a married male colleague is being inappropriate with me or with another female? Is it wrong that because I’m always in the office or traveling for work, I lean on my coworkers (mostly married men) to meet my emotional needs?

4. Questions relating to dating.

What does a healthy friendship look like with a man? Can single women and single men of comparable dating ages “just be friends,” and if so, how? Is it wrong for me to take initiative with a man to pursue a potential romantic relationship with him? If I go out of my way to try to meet a husband, does that mean I’m not trusting God’s sovereignty? What do you think about online dating? How can I trust God when I’ve been dateless for a decade? With regard to contemporary dating practices, what’s off-limits for Christians? What does it look like to date Christianly as an older single? When we talk about best dating practice, how do we distinguish between biblical principle and cultural preference? As an introvert, how am I supposed to meet a man when, the older I get, there are fewer “natural” places for me to do so?

5. Questions relating to sexual ethics.

Is it possible that I’m single because God is punishing me for my past sexual promiscuity? Are you ever tempted to compensate for not having sex by indulging in something else—like pornography, masturbation, romance novels, romantic comedies, soap operas, food, or exercise? What are some good disciplines for older dating/engaged couples to promote sexual purity? Can I go on a long vacation with my boyfriend, and can we share the same hotel room if we’re not having sex? Why or why not? Can we sleep in the same bed and/or spend the night together if we’re not having sex? Why or why not?

6. Questions relating to family life in the church.

If I’m same-sex attracted, how do I develop godly, intimate friendships with other sisters in Christ, and how do I communicate with them about this aspect of my life? How can I develop godly friendships with brothers in Christ, single and married? What are some things of which I need to be aware in my relationships with male ministry colleagues? When you’re in ministry with a married man, do you go out of your way to include his wife when you communicate with him on emails, texts, and so on? How am I supposed to fit into my church family, when I feel invisible every Sunday as an older single person without children (or as a divorced or widowed woman)? Why does my local church’s women’s ministry only offer Bible study at 10 am on Thursday morning? Why does my church not address the challenges of single mothers and think about how to make us feel welcome in social settings?

7. Questions relating to culture and theology.

What is the “gift” of singleness, and how do you know if you have it? Why does our culture exalt marriage over singleness? When God says, “It is not good that the man should be alone,” does that pertain only to marriage? Does it also pertain to men and women partnering in gospel ministry? What difference does it make to single people now that there will be no marriage in heaven? What bearing does this have on our relationships, and how can we train ourselves to think biblically about being single in light of the new heaven and the new earth? How can my suffering become spiritually productive? As a single woman committed to following Jesus, how can my commitment to sexual purity be spiritually productive among my non-Christian friends, who consider this utterly bizarre?

Lots of questions, I know. Is the teaching ministry of your church answering them for singles in your midst?

In all this, may we rely for wisdom upon our great high priest—the one who embraced singleness to the glory of his Father, who in every respect has been tempted as we are, yet is without sin. In every conversation, may God equip us to play the role of the faithful groomsman, gladly pointing the church to her Bridegroom: “I must decrease, but he must increase!”

Mary Willson

Mary Willson serves as the associate director of women’s initiatives for The Gospel Coalition. Mary is presently engaged in Old Testament doctoral studies at Trinity Evangelical Divinity School. She also holds an MDiv and ThM from Gordon-Conwell Theological Seminary. Alongside her academic work, Mary enjoys teaching and training others to teach the Scriptures, especially in the context of the local church. She has many nieces and nephews who make life all the more wonderful and rambunctious.

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