A Winsome Strategy to
Win-Some for Jesus
in a Negative World

There has been some rhetorical debate centered on social media regarding the use of the word, “winsome.” Dictionary.com gives this definition: “sweetly or innocently charming; winning; engaging…”I believe it’s been said that if you are “winsome,” then, in the Christian sense, you could “win some” to Jesus.

In an article by First Things associate editor James R. Wood, he addresses our approach in a culture that has moved from neutral toward Christianity to negative. He references the contention of Aaron Renn of American Reformer:

There was a “neutral world” roughly between 1994–2014 in which traditional Christianity was neither broadly supported nor opposed by the surrounding culture, but rather was viewed as an eccentric lifestyle option among many. However, that time is over. Now we live in the “negative world,” in which, according to Renn, Christian morality is expressly repudiated and traditional Christian views are perceived as undermining the social good.

Wood contends: “…the ‘negative world’ is a different place. Tough choices are increasingly before us, offense is unavoidable, and sides will need to be taken on very important issues.” He goes on to say: “If we assume that winsomeness will gain a favorable hearing, when Christians consistently receive heated pushback, we will be tempted to think our convictions are the problem,” adding, “An excessive concern to appeal to the unchurched is plagued by the accommodationist temptation.”

Rod Dreher, writing at The American Conservative, sheds some light on the Renn timeline, saying that the era before 1994 could be described as “positive world.” He writes:

I have described America as a “post-Christian nation,” meaning not that there are no Christians, but that Christianity is no longer the story that most Americans regard as explaining who we are. You might think that’s great, you might think that’s terrible, but it’s simply true.

Dreher and Wood seem to be advocating for a new understanding of the world we live in and a bolder strategy to reach an increasingly hostile world. Dreher adds: “The moment for Christians to love our enemies and pray for them will never pass, this is true. But the idea that they will embrace us, or even tolerate us, if we just be sweet is no longer viable.” But he states, “I don’t advocate at all hating our enemies.”He warns:

Winsome World Christians are failing to prepare themselves, their families, and (if pastors) their flocks for the world that exists today, and the world that is fast coming into being. Again, I am thinking of the pastor I argued with who believed that he didn’t need to speak about gender ideology to his parish (“I don’t want politics in my congregation”) because, as he explained, if he just keeps winsome teaching Biblical principles, all will be well. I am certain that man believed he was taking a virtuous stand against fearmongers and alarmists like Dreher. I think it was cowardice.

Dreher warns,

“American Christians have to learn how to endure persecution without capitulating to apostasy or to hatred.”

Here’s a quote from Twitter from recent Meeting House guest Erik Reed of Knowing Jesus Ministries and pastor of The Journey Church near Nashville:

“The overly winsome, tiptoe approach some of our evangelical thought leader stake on secular ideologies like abortion, gender, and sexuality forgets the enormous number of Christians facing pressures to conform. Their silence and lack of clarity isn’t helping those people at all.“

Reed adds:

“With a church of 1500+ ppl, our staff/elders can’t afford to ignore the realities our kids, students, college kids, and adults face each day. Secular progressive ideology is the air they breathe in this culture… They’re not helped if we are silent or ambiguous on these issues.”

That is a powerful image and can lead to this question: What air are you breathing? Are we breathing in the toxic air of the world and the culture that can pollute our souls, or the “fresh air” of the wind of the Holy Spirit?

We can also consider if we are boldly standing on truth or if our lives are reflecting compromise. There is talk of a “third way” on issues that the Bible speaks clearly to, in order to be more appealing to the world. While Jesus calls us to reach the world, He doesn’t direct us to appeal to it by watering down the gospel.

Scripture speaks to a host of issues -directly through proclamation or indirectly through principle. We can adhere to truth and maintain a Christ-like spirit. Podcast host Josh Daws tweeted:

We need to distinguish between winsomeness as a strategy and winsomeness as a demeanor. Winsome strategy seeks to engineer a response from those we’re trying to win. Whereas a winsome demeanor is focused on Christ-like interactions rooted in truth regardless of the response.