Ross Douthat's Podcast is Proof that Winsomeness is Still a Thing

Three years ago, I registered a complaint about the evangelical debates over “winsomeness.” Specifically, I said that these debates almost all treat interpersonal dynamics as Internet things. Arguing about civility is what people do when technology and mobility allow them to withdraw from the real world.

Abandoning civil discourse is a romantic idea for a writer whose daily bread depends not on cooperation and mutual trust among laborers but on generating high amounts of page views for a remote employer. Winsomeness seems like cowardice—to somebody whose main experience of human connection is scrolling. The redefinition of how we speak to each other is tied closely to the redefinition of what “each other” means. You don’t cheerlead for winsomeness in a life that is embedded in offline relationships. You simply practice it, because the alternative is that these relationships combust. You only think of winsomeness as a thing that you might choose or reject when that choice does not carry much vocational or existential weight for you. And that is only true for most of us if what really matters in our lives is the Internet.

My point is that when people want the company of others, when they desire things like conversation, friendship, and cooperation, they don’t immediately frisk the people in their lives for the wrong political views. They don’t agonize over whether to say “hi” or “how are you doing,” worried that such friendliness might communicate wholesale endorsement of their worldview. A posture of welcome to people prior to showing their ideological papers is just the normal, “people” thing to do. The only reason essays and blog posts can make it seem abnormal is because it’s precisely people that are missing from our digitized existences.

Ross Douthat

’s podcast “Interesting Times” is one of the best podcasts out there right now. I say this as someone who is very selective and impatient with podcasts. I don’t cruise through every workday with a stable of talky podcasts in my ears. I don’t wake up every morning and refresh NPR’s feeds. I find most podcasts hard to listen to and impossible to finish. But Ross’s show has become “must listen.”

Two reasons for this.

One that I’ll briefly note is that Ross is a master questioner. The besetting sin of podcasters these days is to play the publicity game well enough to get a thoughtful guest, and then reveal how little of the guest’s work they know by offering them the most banal questions one right after another. I have a feeling this is driven by a desire to get more guests and more episodes out there, and the best way to do this is to 1) offer softballs and 2) focus on promotion/guest acquisition more than show prep. A couple years ago I did a fair number of podcasts around my book, and I was struck by how many interviewers basically asked me to summarize the contents of the book. (For what it’s worth, as an author, I have not seen any evidence that podcasts have a meaningful effect on book sales; I suspect that listeners take boring podcast interviews to mean that the guest’s book is likewise boring, and who can blame them?)

But the other reason this podcast succeeds is that Ross does a great job pressing on his guests in respectful but forceful ways. He doesn’t let them get away with non-answers. He doesn’t avoid tough questions, and he doesn’t pivot off intractable disagreement as soon as he can. Yet he never comes off as rude, arrogant, or condescending. He takes his guests seriously as thinking adults. Ross Douthat is winsome!

Two episodes stand out for demonstrating this. His interview with Peter Thiel contains numerous tense moments. To be clear, Ross isn’t a bully. He wants people to appear on his show. But with Thiel, Ross doesn’t hesitate to force Thiel to answer straightforward questions like, “Is it good that the human race survives?”

Ross isn’t trying to embarrass Thiel. But he’s not trying to let him hide behind jargon, either. This is an amazing moment because listeners can hear and see Thiel struggling to decide whether he can fully endorse the survival of the human race. And this peels away rhetorical layers so that everyone can see the transhumanist project, at least for a few seconds, in high definition.

There was a time when people talked about Christian apologetics as the art of getting secular people to own the limitations of their own worldview. I’m not sure if a lot of people think Christians ought to be doing that nowadays. It sometimes seems like the main thing going in Christian apologetics and public theology is trying to draw tighter and tighter circles around the right tribe, and going all in on political solutions that will help us avoid, as much as possible, ever encountering anything outside the circle. Because if we encounter anything outside the circle, we may become corrupted through our own civility.

Douthat models here how to respect our ideological opponents enough to let them prove us right. He’s asking the right questions, and pressing for an answer, and he gets an astonishing moment of clarity that doesn’t wash away just because Ross accepts Thiel’s eventual answer. It’s a masterclass of respectful, forceful, unequivocal confrontation.

The interview with Doug Wilson is another example. There’s no single moment as striking as what happens in the Thiel interview, but if you listen carefully to the whole episode, you’ll hear Ross pushing Wilson in particular to explain two things: 1) how his political theology would come to fruition in the USA that currently exists, and 2) how his methodology and rhetoric can maintain a coalition that excludes antisemites and other transparently evil people. Wilson struggles to give plausible reasons, especially as Ross continually asks for particular examples. One revealing moment, concerning Wilson’s theocratic tendencies, is here:

Wilson: So in Mosaic law, there is no express penalty for fornication. There is a penalty for marital fraud. So, if a woman represents herself as a virgin, and she’s not a virgin, then there were civil consequences. But that had to do with things like inheritance and who the father of the baby was — all of that.

Douthat: So we’re going easy on fornication.

Wilson: Well, we’re following the Bible. So what I want to do is I want to be a biblical ——

Douthat: But we’re not completely. I mean, at least in the discussion we just had, you did not advocate stoning adulterers, right?

Wilson: No.

Douthat: So you’re deciding which particular aspects of the Bible should apply.

Wilson: Well, yeah.

Douthat: There are biblical precepts that allow for the stoning of adulterers in the Old Testament.

Wilson: You are correct. Right.

Douthat: And you’re not in favor of stoning adulterers.

Wilson: Well, I’m not against it, either.

Douthat: You are open to it.

Wilson: No, this is the thing: Politics is the art of the possible.

Listeners can judge for themselves whether Wilson is coherent here. And that’s the thing. Without trying to peg Wilson as a would-be Christian emperor, without affectation, Ross simply walks Wilson into a dilemma whether Wilson cannot really explain how his views intersect with reality. He lets the right questions do the work instead of the right allegations. Yes, he lets Wilson expand on his views, and if your sole criteria for righteousness is keeping the Wrong Kind of People out, you may think Ross is guilty. But an attentive listener knows what’s going on. It’s quiet, adult, respectful deconstruction. It’s holding ideas accountable without holding them in contempt. It’s winsome!

You can see a three-dimensional example of this is in the episode where Ross moderates the conversation between Leah Libresco Sargeant and Helen Andrews on the “great feminization.” Ross pushes both women in appropriate directions. This episode is a little different in that Ross is trying more than usual to be “neutral.” But the episode still rebukes anybody who thinks rigorous disagreement and civility are incompatible, or anybody who wants one without the other.

Look, I think it’s a mistake to talk of “civility” or winsomeness as the most ultimate values. They’re not. Politeness is not the chief of the virtues. But Ross Douthat illustrates that when you get mature adults together, there is a gravitational pull toward trying to hear and be heard, trying to understand what each other is saying, and honest expressions of surprise, dismay, and skepticism. It’s the full range of human interaction that makes Ross’s work as a podcaster so compelling, and vivifies the idea that a liberal society can be one where ideas win and lose without the coercion of law or the dissolution of community.