I listened to an interview where you spoke about acknowledging that people who have problematic views probably experienced some sort of pain in their past that led them to having those beliefs. Does that idea inform the journalism that you do or how you talk to people?
Yes, definitely. It informs my journalism in that I’m genuinely interested in how people came to be the way they are, and I try not to make assumptions about people’s ideologies and inherent worth. I’m generally more curious about people who hold problematic beliefs than I am about people who I agree with. I understand pretty well how you get to the place where I am, but I am fascinated by people who get someplace else, whose life experience maybe doesn’t seem that different from mine on the surface yet they wound up with an entirely different worldview. Because I’ve been really curious, I have been able to gain the respect of a fair number of people who I don’t agree with, even before I was doing the podcast. I covered McCain’s campaign and I covered the right for a long time, and I’ve always been able to have good relationships and good conversations with people that I cover. I have been told at least that they respect me, and I think that they do because I don’t assume a caricature all of the time. Also, I’m open about what I believe. Conservatives assume all journalists are liberal and they prefer for people to at least admit it.

Is it ever hard for you to put that empathy into practice?
Oh yeah, definitely. I was at CPAC (the Conservative Political Action Conference) this year–and it was obvious in retrospect, but not obvious when it happened. I started talking to this kid who had a Pepe pin and that should have been my tip-off, and he’s just a straight up white nationalist. A truly white nationalist. I fell for it basically. I got trolled. Like he “owned a lib” because he made me angry. He was just being willfully stupid, and I’m sorry, even saying that I feel kind of bad–I don’t usually talk that way about people. He was like, “White people came here first, why shouldn’t we run the country?” I don’t have anything to say to that. I’m sure someone hurt him at some point, but in the moment I could not maintain my professional curiosity.

Do you think empathy can be a tool to break out of that troll trap?
Empathy can be a tool. I also think empathy doesn’t have to be in person. I think it is important to develop a general empathy for people. It’s weird–I think you have to generally understand that people are individuals and everyone has their own story and in individual situations, it depends whether empathy is the right way forward. If you are someone who is marginalized in some way–I never want to ask a black person to face-to-face empathize with a racist. But I think that it can be powerful to ask people why they believe what they believe, if you are in a situation where it’s safe to do so. I’ve found that to be a somewhat magical solution to the escalation of bad feelings.

You said in another interview that when we speak with people we disagree with, we have to get out of the headspace where we try and change their minds or find common ground, but, rather, that we should try to understand each other. Can you talk about what it means to understand someone?
On some level I think you have to stop thinking about the conversation in terms of a game. The understanding in and of itself has to be the thing that you’re trying to do. If you have an agenda as far as why you want to understand someone, like, I want to understand where you’re coming from so I can convince you to believe something else, that tends not to work. People are real sensitive to that. People can tell what you’re doing is just trying to hook ’em. Weirdly, if you genuinely seek to understand where someone is coming from, you have a better shot at changing their views. It just can’t be the primary reason why you’re doing it. If you seek empathy for its own sake, there can be rewards beyond that, but you have to also be prepared for the fact that you may not get anything but understanding where they’re coming from. I don’t think you give up the right to be seen even if what you believe is horrible. Sometimes it’s actually really good to know that someone is really horrible–to see them as they are.

Has there ever been an episode of With Friends Like These that completely changed the way you looked at an issue?
I would not say there has ever been a complete turn around on anything. One of my early interviews with my friend Ira Madison was a real moment of impact because he shifted the way I thought about my own discomfort. I was talking to him about the phenomenon of being someone’s black friend. He’s black. He’s my friend. He’s also from Wisconsin. He’s used to being one of the only people of color in a group and he’s used to being a white person’s only black friend. I was talking to him about that and I got into talking about how I personally tried to increase the amount of diversity in my circle of friends. I’ve tried to go out of my way to speak to people who are different races, gender identities, etc. and I said something about how I felt weird doing that and how it’s a place where intentionality can feel strange. To be intentional about making a friend feels really weird and uncomfortable. Ira said, basically, “You know, Ana, the lives of black people are uncomfortable.” That woke me up. I probably knew that before but it made me realize that my own sense of, I don’t know, it feels really strange to go out of my way and make friends, was just a stupid, minor concern. The experience of marginalized people in America is basically like that all the time, having to be intentional about your relationships.