We Are not Called to Be Winsome

Remember way back to those halcyon days of “Neutral World?” Neutral World, as described by Aaron Renn in his recent First Things article, “The Three Worlds of Evangelicalism,” was the period of time spanning 1994 to 2014.[1] Renn maintains that during that period the broader culture was neither negative nor positive in relation to Christianity, and that it was seen as one legitimate convictional option among many in the public square. Evangelical leaders during that period strove for cultural engagement, often in an urban context, as opposed to their more rural, culture warrior predecessors. The byword for that Christian engagement was “winsomeness.” All right-thinking evangelicals were encumbered with the task of being winsome Christians: inoffensive, socially attractive, and above all, loving. Actually, those are pretty desirable traits. Especially being loving, if by that we mean the kind of love displayed on the cross. However, according to Renn’s taxonomy somewhere after 2014 the wheels fell off the winsomeness bandwagon. Even Tim Keller, the sensei of winsome, was not able to retain access to elite circles. Renn notes that Princeton Seminary, following outrage from students, rescinded the 2017 Abraham Kuyper Award bestowed upon Keller:

It’s hard to think of anyone more thoughtful and winsome than Keller, but students protested his award because he subscribes to a gender theology that restricts ordained ministry to men and affirms men as the head of the home.[2]

Yet, while the green pastures of Neutral World are a distant smudge in the rear-view mirror, (Renn says we now live in Negative World[3]) that compulsion to be winsome Christians is still floating around in the back of the evangelical psyche. That’s why so many evangelicals get their Doug Wilson delivered in a plain brown wrapper in the dead of night when no one can witness them giggling about his lexicological dexterity and transgressive truth-telling.

The Tyranny of Winsomeness

In reality, when we think about being winsome we are generally thinking about not giving offense at precisely those points that the world finds objectionable about this whole Jesus schtick. We forget that there is always, in every age, going to be something about the proclamation of the whole counsel of God that no amount of high fructose corn syrup can be added to make it more palatable for sinners, who remain entrenched in their rebellion against the Creator.

Moreover, anxious evangelicals need to remember that we are not the ones who keep bringing up the points where we go awry of conventional moral wisdom. Rather, it is the moral revolutionaries of our society who just keep banging on and on about the next project of emancipation from the divinely decreed order of creation. Make no mistake, it is on this particular battlefield where the surrounding secular culture is obsessed with demanding the church’s surrender. And winsomeness is laughably ineffective body armor in this battle. An often misattributed quote provides a bracing tonic for those of us still struggling to find a way to offer an inoffensive gospel:

If I profess with the loudest voice and clearest exposition every portion of the truth of God except precisely that little point which the world and the devil are at that moment attacking, then I am not confessing Christ, however boldly I may be professing Christ. Where the battle rages, the loyalty of the soldier is proved; and to be steady on all the battle-field besides is mere flight and disgrace to him if he flinches at that point.[4]

That’s the point, isn’t it? The dominant culture has no problem whatsoever with certain articles of Christian belief and moral conviction such as the ethics expressed in the Parable of the Sheep and the Goats in Matthew 25. Secularists think we’re swell when we care for the sick, the poor, the homeless, and the prisoner – as long as we leave the Jesus bits out. Yet, Christian anthropological convictions that focus on the sanctity of human life, the telos of the human body, and the sacramental character of the male/female union in marriage constitute a massive burr under the secular saddle.

Further, if we are being honest, it’s not just secularists who find biblical convictions about these topics embarrassing if not downright irritating. Christians can become so attuned to just how nutty and, frankly, repugnant our anthropological definitions and moral convictions sound to the world that we cringe a little when they are openly proclaimed. I actually experienced that personally a while back when a godly priest, faithfully expositing the Word of God from the pulpit, boldly declared that Christians needed to stand firm against the pressure exerted by the sexual revolution. As he named same-sex marriage and transgenderism I flinched a little, worried how the more progressive evangelicals and nominal Christians in the congregation would hear those words. Barely articulated, in the back of my mind, I felt that we had just offended the jealous god of winsomeness.

The Love Hammer

Yet, winsomeness is not going to save us from hard times in this present darkness (Eph. 6:12), let alone serve as an effective evangelistic strategy. In response to Christianity’s sand in the eye of the body politic, massive amounts of social, economic, and legal pressure are applied to churches, Christian organizations (like schools), and individuals. First comes the nudge of social opprobrium, then the push of economic retaliation, and finally the shove of legal sanctions. Somewhere along the “nudge” end of the spectrum of response the offending Christian institution or individual is bombarded with sentimental, emotivistic language usually employing what I call the love hammer. That sounds like something from an old Austin Powers movie, but what I mean by it is when love is used as a convenient rhetorical hammer to be applied to the heads of Christians. We are chided for not being loving in just the way the imaginary jesus (sic) they made up in their own heads would be.

Here’s a recent case in point: In May of 2022 a teacher at the Christian Academy of Louisville, Kentucky gave an assignment in which students were to write a letter to a hypothetical friend “struggling with homosexuality.” The assignment goes on to state “… The aim of your letter should be to lovingly and compassionately speak truth to the person you’re talking to in a way that does not approve of any sin. Instead, TRY TO PERSUADE THEM OF THE GOODNESS OF GOD’S DESIGN [all caps in the original] for them.”[5] Obviously, the standard of Christian winsomeness was embedded in this assignment. Yet when news of this Christian school teaching Christian ideas to Christian students seeped out into the community there was outrage. One 2002 alumna of the school started swinging the love hammer like Thor wielding Mjölnir when she heard about the assignment. She opined to a local newspaper, “But I was still really disappointed because I’ve been gone 20 years, and I would’ve hoped that in 20 years maybe they would have learned that love is the way to go, as opposed to the fire-and-brimstone hate. But it doesn’t seem like it to me.”[6] It’s revealing that in an assignment that directly appealed to Christian love, this alumna saw “fire-and-brimstone hate.”

Thinking Christians easily recognize that what is being appealed for when dewy-eyed sentimentalists chant some variation of the “love is love” mantra is actually license. In contrast to antinomian sentimentalism, authentic Christian love always desires and acts for the genuine good for the beloved. God alone reveals, first in creation and then supremely through his Word (see Ps. 19), what constitutes the genuine good. Yet, sometimes (most times) “beloveds” don’t want the genuine good. They want to “suit their own passions” (2 Tim. 4:3) and for anyone to create obstacles – you know, like winsomely disagreeing – to the fulfillment of those passions is deemed unloving. We fallen humans don’t want the genuine good, so much so that we are willing to employ violence to eschew it; as in crucifying the Lord of glory (1 Cor. 2:8).

Whither now, if not Winsomeness?

What I’m saying here is that winsomeness is not a Christian virtue to be sought at all times and in all places. It had its moment (maybe) as an evangelistic approach, but Christians in Negative World should not be shackled with the guilt of not being “winsome” enough. Yet, if we are not called to be winsome, what exactly are we called to be in this particular cultural moment? Are there any enduring and transcendent attributes Christians should seek to embody while engaging the world around them? In fact, are there any transitory, yet godly attributes enjoined upon us in Scripture that we should strategically adopt? I’m glad you asked.

Let’s assume we all know that we are to “always [be] prepared to make a defense to anyone who asks you for a reason for the hope that is in you; yet do it with gentleness and respect. (1 Pet. 3:15b ESV)” Let’s also assume that we are all on board with the apostle’s imperatives to, “Be watchful, stand firm in the faith, act like men, be strong. Let all that you do be done in love. (1 Cor. 16:13–14 ESV)” Likewise, we, of course, obey Jesus’ command to, “Love your enemies and pray for those who persecute you. (Matt. 5:44 ESV)” You were expecting all of that, so we’re not going there. Instead, I want to offer two lesser-traveled scriptural paths.

Wise as Serpents

To begin with, let’s adopt the method of strategic engagement that the Lord Jesus enjoined upon his first followers as they went out to minister in the “Negative World” of first-century Palestine: “Behold, I send you forth as sheep in the midst of wolves: be ye therefore wise as serpents, and harmless as doves. (Matt. 10:16 KJV)” Sheep among wolves, that is where we are situated again today, and it is certainly an apt description of the church in Negative World.

Be “wise as serpents.” The connotation of the Greek word translated wise is amplified by applying the simile of serpents. In other words, in Negative World be clever, be canny, even crafty. The modifying simile of being “harmless as doves” demonstrates that Jesus is not offering an injunction towards dishonesty but towards prudence.

What does this mean for evangelicals living in Negative World? The context of our Lord’s command is that of being sent out on mission. Thus, when we are about God’s mission in the world this is to be our disposition. There are abundant vectors for applying this instruction from Jesus. First of all, avoid being unnecessarily provocative. Avoid unnecessary conflict. Call to mind historic Christian communities living in the hostile environment of the Muslim world. For centuries these churches have had to manage to remain unyieldingly faithful to Jesus Christ, while not calling down the ire of their Muslim rulers (or neighbors, for that matter). They realize that they may be called to martyrdom for their loyalty to Jesus, but they aren’t rushing to get there.

Similarly, Christians in Negative World need to avoid unnecessarily poking every tender idol of the culture. There will be a time to call out the idols, but when there is a pagan shrine on every corner you need to have the clear unction of the Holy Spirit about which ones to topple first. This isn’t a call to timidity, but to choosing the right battle. Sometimes we are called to side-step one legitimate issue so that we can be confrontational on an issue of greater biblical significance.

Jesus’ encounter with the Samaritan woman at the well in John 4 is paradigmatic at this point. She wants to pin Jesus down in a political/theological argument: Jews say worship only in the Temple in Jerusalem. We Samaritans say worship on this mountain. What do you say, huh? Likewise, Jesus doesn’t get distracted by her domestic arrangement, which he definitely does not endorse. Rather, wise as a serpent, he gets to the salient missional point: “I am the Messiah that both the Jews and Samaritans long for!”

The woman said to him, “I know that Messiah is coming (he who is called Christ). When he comes, he will tell us all things.” Jesus said to her, “I who speak to you am he. (John 4:25–26 ESV)”

Of course, the danger is that such prudence becomes window-dressing for cowardice. Yet, prudence is why there are still Christian churches in Lebanon, Syria, Jordan, Turkey, and other countries in the so-called 10/40 window. Yes, these countries have more moderate expressions of Islam, but Christians have also learned to be wise as serpents and harmless as doves in these places.

Practically, for me as a priest, I want to avoid being drawn into the political imbroglio du jure that would distract me from getting to the juicier, and even more offensive parts of the gospel such as, “Jesus is Lord, whether you like it or not.” This is why I don’t put provocative bumper stickers on my pickup truck. I don’t want to short-circuit giving people time to get to know me so they can hate me for all the right reasons, and not because of some stupid slogan.

Being wise as serpents also means having missional situational awareness. The days of one-size-fits-all evangelistic methods are long, long gone. Similarly, church planting models have to be tailored to fit specific communities instead of assuming prosperous, white, Neutral World, suburbia is the ubiquitous mission field. How do you do that? For the sake of brevity, just check with the One who sent you out on mission for his advice.

Pearls before Swine

Finally, in keeping with the theme of prudence as the new winsomeness, we need to learn to keep our mouths shut – about the right things. Jesus said, “Give not that which is holy unto the dogs, neither cast ye your pearls before swine, lest they trample them under their feet, and turn again and rend you. (Matt. 7:6 KJV)” Back when we lived in Positive World and Neutral World we could count on being given some leeway when we talked openly about topics earlier generations of Christians kept opaque from outsiders. In Negative World we have to relearn not to be exhibitionistic about the “mysteries” of the faith with the unconverted and uncatechized. These are the pearls, the holy things that will be turned against us by the “vincible ignorance” of unbelievers. Early Christians were accused of incestuous orgies and cannibalism because of intentionally malicious pagan misinterpretations of the eucharist.[7] Those pagan conspiracy theories were used against us as warrant for persecution, to “turn again and rend” us.

To this very day, the Divine Liturgy of Saint John Chrysostom contains this line exclaimed by the deacon prior to the celebration of the eucharist: “The doors! The doors! In wisdom let us attend!” In the ancient church (and still in some churches today) that meant that the physical doors of the church were closed, shutting out the catechumens and the unevangelized. Only the baptized, the “illumined,” were allowed to witness and participate in the mysteries of the eucharist. This was in direct response to our Lord’s admonition to keep the holy things from being profaned.

St. Paul warned us that, “The natural [that is, unregenerate] person does not accept the things of the Spirit of God, for they are folly to him, and he is not able to understand them because they are spiritually discerned. (1 Cor. 2:14 ESV)” We need to resist flippantly referring to the things of the Spirit around unbelievers. For Christians in the sacramental stream of the faith, we need to adopt earlier generations’ canniness about divulging the theology of the mysteries to those who will just trample them underfoot. Likewise, Christians in the charismatic stream of the faith need to have a greater awareness of things that can be spoken about in the household of faith (Gal. 6:10) and that which can be expressed among scoffers and mockers.

Living in Negative World among the unconverted, I resolve to know nothing but Jesus Christ and him crucified (1 Cor. 2:2). That will be scandalous enough. Indeed, it will not be winsome, but it is the power of God unto salvation (Rom. 1:6) and the only message that can bring people out of darkness and into his marvelous light (1 Pet. 2:9).


  1. Aaron M. Renn, “The Three Worlds of Evangelicalism,” First Things, February 2022, accessed May 19, 2022, https://www.firstthings.com/article/2022/02/the-three-worlds-of-evangelicalism.
  2. Renn, “The Three Worlds of Evangelicalism.”
  3. Renn identifies Negative World as the period from 2014 to today. In Negative World, Christianity is seen as harmful to public welfare and being a known Christian is a social negative. Positive World existed prior to 1994. In Positive World Christianity was seen as beneficial to society and being known as a Christian enhanced social standing.
  4. Elizabeth Rundle Charles, Chronicles of the Schoenberg-Cotta Family, (New York: T. Nelson and Sons, 1864), 276.
  5. Lucas Aulbach, “Homework at Christian Academy of Louisville: Persuade your friend to stop being gay,” Louisville Courier Journal, May 15, 2022, accessed May 19, 2022,https://www.courier-journal.com/story/news/education/2022/05/13/christian-academy-louisville-lgbtq-homework-assignment/9765498002/.
  6. Aulbach, “Homework at Christian Academy of Louisville.”
  7. Richard J. Goodrich, “Cannibals at an Orgy,” November 24, 2020, accessed May 19, 2022, https://medium.com/lessons-from-history/cannibals-at-an-orgy-45f478e760ba.


The Revd. Canon Dr. Ben Sharpe

The Revd. Dr. Ben Sharpe is a church planter, the Rector of Christ Church in Winston-Salem, NC, and Canon Missioner for West Virginia and Appalachia in the Anglican Diocese of Christ Our Hope, ACNA.

'We Are not Called to Be Winsome' have 2 comments

  1. June 5, 2022 @ 9:05 pm Paul William Erlandson

    I don’t find this article to be useful at all.
    First off, the author does not understand the purpose of being winsome:
    “And winsomeness is laughably ineffective body armor in this battle.”
    That is not the purpose. We are not using it to protect ourselves from harm or sacrifice. Later, he writes:
    “Yet, winsomeness is not going to save us from hard times in this present darkness …”
    Again, that is completely NOT the point of winsomeness.
    Then, when he gets around to giving advice, he says things like:
    “First of all, avoid being unnecessarily provocative. Avoid unnecessary conflict.” which are borrowed directly from the doctrine of Winsomeness.


  2. August 17, 2023 @ 7:31 pm jeff kordon

    In my vernacular (Texan) winsome has always meant “childish” or “naive.” And that’s obviously the correct definition. And I never h3ard anyone trying to day Christians should be “winsome” until 2022. Russel Fagmoore seemed to me to be the origin of it, but maybe it was his boyfriend Tim Keller.


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