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Winsomeness Can Be a Virtue or a Vice

written by Andy Naselli | August 24, 2023

Winning Some vs. Pleasing Some

To want to be winsome is to want to win some—that is, to attractively or appealingly convince others to share your viewpoint. As a Christian, I want to win some by convincing others to see reality and to joyfully follow Jesus as the Savior and King.

This is Paul’s evangelistic burden in 1 Corinthians 9:18–23. He wants to win more people to Christ. He wants to win Jews; he wants to win those under the law; he wants to win those outside the law; he wants to win the weak. He has become all things to all people so that by all means he might win some with the glorious gospel—the message that Jesus lived, died, and rose again for sinners and that God will save you if you turn from your sins and trust Jesus.[1. Thanks to friends who graciously offered feedback on drafts of this article, including Michael Carlino, Josh Daws, Kevin DeYoung, Abigail Dodds, Ben Dunson, Zach Howard, Charles Naselli, Jenni Naselli, Joe Rigney, Aaron Rothermel, and James Wood.]

What Could Possibly Be Wrong with Winsomeness?

The apostle Paul wanted to win some. So what could possibly be wrong with a Christian wanting to be winsome? Nothing necessarily. It’s good to want to be winsome in that virtuous sense. But you should ask yourself some diagnostic questions:

I refer to “sinful people-pleasing” to distinguish it from Romans 15:2: “Let each of us please his neighbor for his good, to build him up.” Here’s how I understand Romans 15:2:

We must please our brothers and sisters for their good in order to build them up (cf. Rom. 13:8–10; 14:19). This does not mean you should become a “people pleaser” who sinfully cares more about what others think than about what God thinks (e.g., Gal. 1:10; 1 Thess. 2:4). The choice is not between pleasing people and pleasing God, but between (1) unselfishly pleasing fellow Christians by edifying them and (2) selfishly pleasing yourself while disregarding others. … One twisted way to selfishly please yourself while disregarding others is to please others in a way that affirms their sin and thus is not for their good. That application is not Paul’s main point in the literary context, but it logically follows from the principle of the exhortation in 15:2.[3. Andrew David Naselli, Romans: A Concise Guide to the Greatest Letter Ever Written (Wheaton, IL: Crossway, 2022), 184.]

Tim Keller’s Winsome Third Way

James Wood hit a nerve in 2022 when he respectfully suggested that evangelical pastor Tim Keller (1950–2023) “maybe subconsciously, thinks about politics through the lens of evangelism, in the sense of making sure that political judgments do not prevent people in today’s world from coming to Christ.” Rather than identifying Christianity with the left or the right, Keller argued for a third way. This “winsome” strategy tends to appease those to your left, create distance from “the deplorables,” and pietistically stay above the fray of complex social and political issues. That approach may be more fitting in what Aaron Renn calls “neutral world” than today’s “negative world,” which is hostile to basic truths that Christians affirm. Wood explains that a concern for the church’s “public witness” lets the culture set the terms for how we engage because we fear that others might perceive us negatively.

The controversy about winsomeness in 2022 highlighted that Christians try to win some with different strategies. I think it’s helpful to classify those different approaches with a four-part taxonomy.

Four Kinds of Winsomeness: A Taxonomy

In Kevin DeYoung’s 2021 article “Why Reformed Evangelicalism Has Splintered,” he proposes a taxonomy of four approaches to race, politics, and gender. He doesn’t name examples of each, but I’ll risk doing so to make it more concrete. My guess is that in 2021 these men generally fit each view based on their instincts and public personas:

  1. Contrite: Thabiti Anyabwile, Russell Moore, David French
  2. Compassionate: Tim Keller, David Platt, Julius Kim
  3. Careful: Al Mohler, Kevin DeYoung, Denny Burk
  4. Courageous: John MacArthur, Doug Wilson, Voddie Baucham

DeYoung describes their perspectives on ten issues: white supremacy, systemic racism, police shootings, critical race theory, Black Lives Matter, Trump, Christian nationalism, wearing masks, sexual abuse, and gender roles. Those ten seemingly unrelated issues line up remarkably in DeYoung’s taxonomy. (For why this tends to happen for political issues, see Thomas Sowell’s A Conflict of Visions: Ideological Origins of Political Struggles.)

There’s another issue DeYoung could add to his list: winsomeness. (I have privately conversed with Kevin DeYoung about this over the past year, and some of what I share here are insights I learned from him.) Here is one way to distinguish four kinds of winsomeness—at least from my perspective as someone who is sympathetic with views 3 and 4 (e.g., I don’t think that view 3 is feckless or view 4 is reckless).

  1. Contrite: Winsomeness is a strategy to be attractive to the left by sympathetically listening to their perspectives and by unmasking and denouncing the right and calling out the church’s sins. Winsomeness is calling out the sins in your own camp since judgment begins with the house of God. (When I use the terms “left” and “right” in this taxonomy, I am painting with a cartoonishly large brush. I am referring to two basic ways of thinking and living in America—two different cultures, two different approaches to politics and the common good. For “the left,” think of large blue cities that disproportionately influence the culture with progressive ideologies that are politically correct. For “the right,” think of small red towns in flyover country that more highly value tradition.)
  2. Compassionate: Winsomeness is a strategy to be attractive to both the left and the right (but especially to the left) by not being culture warriors but instead by being thoughtful and kind. As Kevin DeYoung argues in an essay on Tim Keller, “In 2023 even the most outward-facing church is going to face hostility not of its own making. I fear that anxious evangelicals hope that if they can just be grace-centered enough, contextualized enough, do enough to serve the community, and make clear that they are not Republicans, then unbelievers will turn to Christ. Of course, Keller never makes such an outlandish claim, but when we emphasize (sometimes necessarily) the Church’s failure to adapt to a changing world, we can miss the biblical truth that those who hated Jesus will hate his followers (John 15:18), and that the god of this age has blinded the minds of unbelievers (2 Cor. 4:4).” This view functionally operates as if we are still in a “neutral world.”
  3. Careful: Winsomeness is a strategy to be attractive to both the left and the right by being thoughtful and kind, especially in personal relationships. At the same time, we live in a “negative world” and thus cannot be nice enough to appease those who think our moral convictions are evil; we must correct error and engage the culture war on certain issues such as abortion and transgenderism.
  4. Courageous: Winsomeness is a strategy to be attractive especially to the right (as well as to those on the left who have become disaffected) by boldly speaking the truth and standing firm. We should not be sinfully harsh, but neither should we worry about offending people who support murdering unborn babies and mutilating children in the Orwellian name of “reproductive freedom” and “gender-affirming care.”

A person’s vocation may distinguish whether in a particular situation he is more aligned with view 3 or 4. For example, the way a pastor privately counsels someone may differ from how a statesman publicly speaks.

We might say that views 1 and 2 are more concerned with building bridges, and views 3 and 4 are more concerned with building walls (which is not to say that views 1 and 2 are unconcerned with building walls or that views 3 and 4 are unconcerned with building bridges). This is how Kevin DeYoung contrasts himself with Tim Keller:

Though I hope to be kind and careful, my public ministry has often involved correcting error, guarding the truth, and warning against creeping liberalism. By contrast, though Keller usually lands squarely on the traditional side of doctrinal matters, he has a public ministry focused on making the gospel attractive to outsiders, staying out of intramural theological disputes, and warning against extremes. You might say I specialize in building walls, and Keller specializes in building bridges.[4. After Tim Keller died, political analyst Kirsten Powers reflected, “I entered Tim’s church, Redeemer Presbyterian, as a fairly committed atheist. … A year later, I was all in with Christianity. And not just any Christianity—I had signed up for Tim Keller’s brand of evangelical Christianity, or at least what I thought was Tim Keller’s brand of evangelicalism. … Ultimately, evangelicalism ended up being quite harmful to me and to many people I care about, and I can’t imagine I would ever have signed up for it but for Tim’s expert apologetics. When I say I signed up for Tim Keller’s brand of evangelicalism, I mean I signed up for what I heard from the pulpit, which never included teaching about homosexuality or abortion being a sin or men being the head of the family. But as I became more involved in the church, I learned that these were in fact core teachings. It was more through peer pressure than any sermons that I started to conform to teachings that left me feeling unsettled and confused. Slowly, I lost myself as I attempted to conform to a theology that had the effect of disempowering me and alienating me from myself and many important people in my life” (“My Complicated Feelings about Tim Keller,” Substack, 24 May 2023).]

Views 1 and 2 tend to punch right and coddle left, and views 3 and 4 are more concerned with problems to the left. What Kevin DeYoung says in his review of Stephen Wolfe’s The Case for Christian Nationalism applies to views 1 and 2:

Winsomeness almost always runs in one direction. The “winsome” folks are careful to speak respectfully and humbly to an LGBT+ audience, while they’re eager to speak “prophetically” to the MAGA crowd. Many conservative Christians are tired of always being on the defensive and always having to communicate their convictions in ways that left-leaning secularists approve of. They want more than a tiny island of religious freedom where we promise not to bother anyone; they want a vigorous defense of what’s true.

So How Can Winsomeness Be Sinful?

I could have titled this article “The Sin of Winsomeness: or, How Winsomeness Can Be Sinful.” The phrase “the sin of winsomeness” isn’t entirely original. In Ben Dunson’s “The Winsomeness Wars,” one of his headings is “The Evil of Winsomeness.” (In this essay I’m building on Dunson’s solid work, which systematically surveys what the Bible says about how to speak to others.) Joe Rigney took a lot of flak from 2019 to 2021 for using the provocative phrase “the sin of empathy.” He simply meant that empathy can be dangerous and that untethered empathy can be sinful. It’s like referring to “the sin of loyalty.” Loyalty is a virtue, but untethered loyalty is dangerous. That’s the sense I intend with the phrase “the sin of winsomeness.”

Winsome is not a bad word. But like any virtue, we can unwisely corrupt winsomeness into a dangerous vice. Untethered winsomeness can be sinful. It’s like the virtue of being gentle. It’s good to be gentle, but in some cases it would be sinful to be gentle. It’s good to be gentle as a general character trait, but it would be sinful to be gentle to a pit bull while it is attacking your daughter. The right virtue in that instance would be valor—courage in the face of danger to forcefully neutralize a lethal threat. (See my article “Are You a Gentle Man? Must We Be Weak to Be Gentle?”)

Winsomeness is sinful when you shift from winning some in a God-honoring way to selfish people-pleasing. There’s a difference between loving your neighbor according to the standard of God’s word and making your neighbor feel loved. That’s a shift from the objective to the subjective—from truth to feelings.[5. Cf. Doug Ponder, “We’re Commanded to Love Our Neighbors, Not to Make Them Feel Loved,” Sola Ecclesia, 5 June 2023.] Winsomeness is sinful when you try to win the approval of certain people the wrong way.

For example, you might want to win pedophiles to Christ. That’s a good desire; Christians should want all sinners to repent of their sins and to trust Christ alone. But it would be wrong to attempt to win their approval by signaling that you tolerate pedophilia (let alone approve of it). It would be wrong to use an Orwellian term like “minor-attracted persons,” which neutrally or even positively labels a wicked disposition.

That example illustrates how winsomeness can go off the rails. I chose pedophilia as an example not because Christian leaders are endorsing it but because it is an extreme issue that illustrates my point. Here are two less extreme examples that hit closer to home:

1. You might want to win an unbeliever to Christ who identifies differently than his sex. For example, a man may identify as a woman and prefer she/her pronouns. So you might use his preferred pronouns to show “pronoun hospitality.” Instead of speaking truthfully, you might decide to play along with his sinful preference that is contrary to reality lest you hurt his feelings. Or you might participate in a rebellious game of make-believe by volunteering your own pronouns (which properly align with your sex) lest you offend someone who is rebelling against God’s created order.[6. See Andrew T. Walker, “Christians Volunteering Pronouns? Capitulation to Falsehood Is Not Christian Kindness,” American Reformer, 19 August 2022; Rosaria Butterfield, “Why I No Longer Use Transgender Pronouns—and Why You Shouldn’t, Either,” Reformation21, 3 April 2023.]

2. You might want to win unbelievers to Christ who don’t think that it’s sinful for a man to be married to a man or for a woman to be married to a woman. So you might refer to people who identify as LGBT as “sexual minorities.” You might intentionally avoid mentioning that God designed marriage for one man and one woman, and you might intentionally avoid explaining that one cannot deny that truth and be a Christian in any meaningful sense. You might instead say that Christians are obsessed with policing what others do in the privacy of their bedrooms while hypocritically being guilty of much worse sins. You might say that the Bible merely whispers about sexual sin but shouts about greed and gossip and religious pride.[7. In 2019, J. D. Greear said something like this in a sermon and credited Jen Wilkin. For that clip followed by Robert A. J. Gagnon’s critique, see the documentary “By What Standard? God’s World … God’s Rules” (Founders Ministries) from 1:32:42 to 1:36:55. For J. D. Greear’s retraction, see J. D. Greear, “Should You List Your Own Pronouns + Do You Regret Saying the Bible ‘Whispers’ about Sexual Sin?,” J. D. Greear Ministries, 4 September 2022.]

How Should We Then Be Winsome?

I like how James Wood exhorts pastors and political conservatives:

  • To pastors: “Speak the truth and stand firm. Help your people stand firm against the destructive lies and false accusations dominant in our day. Be a good shepherd. Take the hits from the wolves. Lay your life down for the sheep.” In other words, encourage and protect sheep, fight wolves, and correct fools.
  • To political conservatives: “Focus on seeking justice, speak the truth, and stand firm. Don’t let an obsession with appearing winsome hinder us from a robust pursuit of winning some of our cultural battles for the common good.”

It’s good to want to do what you can to win some to Christ. Be flexible where you can be flexible for the sake of the gospel. If you offend people, make sure that what is offensive is the truth.

Proclaim the truth of the gospel. All of it. It’s not loving to edit out the offensive parts.[8. Cf. Kevin DeYoung, “Seven Principles for Cultivating a Christian Posture toward the World,” WORLD Opinions, 10 May 2022.]

And proclaim the truth of reality. Just as it’s not loving to affirm an anorexic young woman by complimenting her skeletal figure, so it’s not loving to affirm evil ideologies like critical theory—even if it’s a strategy to gain a hearing for the sake of the gospel.

The issue really boils down to this: We must not care about what other people think of us more than we care about what God thinks of us. So we should beware that in our winsomeness we do not sin.

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