How to Talk to Friends and Family Members who Support the Regime

“You can resolve to live your life with integrity. Let your credo be this: Let the lie come into the world, let it even triumph. But not through me.” - Aleksandr Solzhenitsyn

How do we talk to people we love who support what Trump is doing? Most say, “I won’t talk to them, it’s useless.” I disagree. It will take all of us (Republicans, Democrats and Independents) to save the Republic. In order to do that we need to build bridges and have crucial conversations. As David Brooks writes, “What Is Happening Is Not Normal”.

When it comes to hard conversations it’s best to start small. This week, I suggest talking face-to-face with someone you love who supports the Trump administration.

Here’s an example of a conversation I had awhile back that was life-giving for me. I have concerns about President Trump’s love of dictators like Putin in Russia and now Bukele in El Salvador. It worries me when he calls himself a king or talks about a third term. I was distressed by January 6th, a failed attempt to disrupt the peaceful transfer of power. So, I asked a person I love and respect who is very involved in Christian nationalist circles to have lunch with me.

Do not attempt this when you are emotionally dysregulated. If you’re not calm your conversation will be counter-productive. Get your nervous system regulated before talking about anything challenging. It might help to exercise before your meeting, go for a walk, take some deep breaths, and then lower your expectations to zero. Also, don’t attempt to cover a dozen things. Just pick one or two that feel important. You might even choose issues your Trump-supporting friend or family member might care about.

Here’s how it went for me. This person and I had lunch. First, I listened to what he liked and didn’t like about Trump 2.0. I did not engage in debate. After listening I told this person how much I loved and admired them. Be honest but lead with kindness. Do you like feeling attacked? Yeah, me neither.

Then I shared my concerns about protecting checks and balances and the rule of law. This was awhile back, so I said the budget needs to go through Congress, and it concerns me that Trump is not doing that with tariffs and DOGE. I told this person that I was afraid that releasing the Founder of the Silk Road would erode confidence in the fairness and impartiality of our entire legal system. They didn’t know that that had happened, or who the Silk Road guy was. Remember: We all live in personalized media ecosystems and this makes it easier “to not know” what is being done in our name.

My conversation went well. It felt like doing something instead of nothing. Anxiety comes from feeling powerless and out of control. This lunch gave me a sense of having tried. In the end, I put the ball in this person’s court and said, “We probably won’t agree on what crosses a line, and that’s fine, but if anything ever feels immoral or unconstitutional to you please speak up, because I know your fellow Republicans will listen to you as a lifelong conservative.”

It’s important to help people understand that criticizing something a fellow Republican is doing doesn’t make the critic a Democrat; it simply makes them brave.

Judge Harvie Wilkinson III, a lifelong Republican appointed by Ronald Reagan and a member of the conservative Federalist Society, just unanimously upheld the ruling requiring the US government to return Kilmar Armando Abrego Garcia to Maryland in the 4th Circuit Court of Appeals (3-0) writing, “It is difficult in some cases to get to the very heart of the matter. But in this case, it is not hard at all.” That’s what courage looks like. He is saying, “It doesn’t matter if it’s my ‘team’ that’s cheating, I am against cheating.”

The goal of bullies and dictators, whatever their politics, is to make us feel scared and powerless. Sebastian Gorka, the Deputy Assistant to the President and the “Counterterrorism Czar” said that anyone advocating for due process for Abrego Garcia could be viewed as “aiding and abetting a terrorist” and “federally charged.” Me. You. Anyone. That’s what bullies do. They threaten.

Remind your friend or family member that their elected representatives work for them not the other way around. Maybe your Trump-supporting family member wants to secure the border and deport illegal immigrants. Fine. Don’t argue every point. Deportations are something Democrats and Republicans have both done in the past. We are way beyond that, frankly. What no administration has done in the past is send illegal immigrants to concentration camps in other countries and pose in front of their cells during Holy Week with a "thumbs up." This is sadism, not business as usual. Sadism is deriving pleasure from inflicting physical and psychological suffering on to others.

Any time you can, find common ground and remind your Trump supporting friend or family member that you both want the same things. Maybe you both love America or believe in due process. Due process after all is what allows, for example, someone to prove they are a citizen if and when they are arrested. Without it, anyone could be nabbed on the street and disappeared before they could gather their documentation and prove their case.

Because you first listened to this person without debating them, you can acknowledge their concerns. For example, “I know you voted for cheaper eggs”, or because you’re pro-life, or because Covid was mishandled. One can still think all those things and call their reps and express their concerns about sending prisoners to stateless zones like they did in the Holocaust.

Have empathy for people who voted for Trump but didn’t know he was going to do all this. Recognize how scary it can feel for someone to lose their certainty. It’s scary to call out your own side. I’ve done it. It’s terrible. I've had people call me names and publicly end their friendships with me because of an article I published which, if anything, downplayed the truth. It hurts. It’s supposed to. When I was working in chaplaincy I had priests tell me I “wasn’t orthodox” and that they “did not trust me” because I liked Pope Francis and supported gay students. That might not sound like a big deal, but when you've built your entire identity and career around being an “orthodox” Catholic, it’s career ending. I had to rethink my entire life. Still, I have never once regretted telling the truth. I have only ever regretted not telling it sooner.

Talk to somebody who supports Trump about your concerns. However the conversation goes pat yourself on the back for staying calm and connected and then release the outcome and go live a beautiful life. Dance in your kitchen and be kind to everyone, dictators hate that.