With over two decades of experience in the nonprofit sector, Venu Gupta has learned that key to building a strong democracy are strong connections—and, more specifically, strong friendships. Gathering in Support of Democracy is a recurring column exploring the essential connections between gathering, community, and democracy building.
Friendship is, among other things, a vital aspect of civic life. It serves as democracy’s essential thread that holds us together. But how does friendship, these bridging relationships, work in practice when powerful forces actively profit from keeping us divided? To attempt to answer this question, I spoke with Cassie Farrelly and Terri Hasdorff, two friends who, on paper, are seemingly very different.
When Cassie and Terri initially agreed to talk with me about their friendship, I thought I’d end up writing about political differences. Cassie is a registered Democrat who works in public media and has a background in nonprofit organizations and community development. Terri is a conservative Republican consultant who ran for Congress in Alabama and authored Running Into the Fire, which discusses why Christians need to engage in politics. At a glance, they are what could be considered opposites on the US political spectrum.
It turns out that getting better at having friendships across political ideologies, makes you better at being a friend to anyone—family members, colleagues, neighbors.
Yet our conversation focused less on political differences and more on the realities of navigating a friendship with someone who isn’t like you. It turns out that getting better at having friendships across political ideologies makes you better at being a friend to anyone—family members, colleagues, and neighbors.
While bridging across differences is key to a functional democracy, building interpersonal understanding across political beliefs requires extra willpower, especially in an environment where division is amplified for political and economic gain.
Start with Respect, Not Agreement
Cassie and Terri’s friendship began in 2015 as part of the Presidential Leadership Scholars program, which brings together leaders from different sectors to learn from the presidencies of George W. Bush, Bill Clinton, George H. W. Bush, and Lyndon B. Johnson. The program’s approach to leadership explicitly challenges participants to seek understanding and engage in meaningful interactions with others whose life experiences and perspectives are different from their own, even if those interactions are uncomfortable.
“It starts with respect,” Terri explained. In meeting Cassie during the program, Terri quickly learned that “[Cassie] is brilliant, self-made, and has overcome a lot to get where she is today.”
This isn’t simply polite tolerance. “I trust in my bones; I know in [Terri’s] heart that she cares about other people,” said Cassie. “At our core, we [both] want a safe society where people can live their best lives.” Both women recognize and value the humanity and goodness within each other, and that is a critical starting point.
In Mónica Guzmán’s book I Never Thought of It That Way: How to Have Fearlessly Curious Conversations in Dangerously Divided Times, assuming good intent is the foundation of bridge-building friendships, as I discussed in the first article of this NPQ series. When we start believing the other person cares about something meaningful—even if we disagree about solutions—we create space for dialogue rather than defensive positioning.
Alongside Guzmán, psychotherapist Esther Perel’s work offers another lens: the ability to hold paradox. Cassie and Terri show us how you can respect someone deeply while disagreeing with aspects of their worldview. We don’t have to choose between caring about someone and maintaining our convictions.
“At our core, we [both] want a safe society where people can live their best lives.”
“You have to be open to hearing someone else’s experience,” Cassie observed, “even when you don’t agree with their conclusions.” This was a critical lesson for Cassie as it taught her to get comfortable with other people’s vulnerability. “You have to learn to sit with, not act on,” said Cassie
This also connects to Prentis Hemphill’s work on healing justice—how transformation happens when we stay present with difficult emotions rather than immediately reacting. Both Cassie and Terri have experienced and worked through this together. They are not trying to convert each other but are instead creating space for each other to exist fully, while allowing that proximity to teach them something new.
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Approaching with Curiosity over Certainty
“Every point of view has a kernel of truth,” Cassie explained. “It is your job to find that kernel of truth.” Guzmán talks about this in her book when she describes “The CARE Framework for Good Questions,” guiding readers to ask good questions that follow CARE: curious, answerable, raw, and exploring. Here are examples of effective questions from her framework:
- “How did you come to believe that?” instead of “Why do you believe this?”: This approach invites people to share their story rather than putting them on trial, asking them to take you on a tour of their thinking process.
- “What am I missing?”: This is described as the most important question we’re not asking. It demonstrates humility and genuine curiosity.
- “What matters to you on this?”: This helps understand the underlying values and concerns driving someone’s position.
- “Where are you on [topic]? Tell me how you got there”: This question works particularly well for contentious topics because it focuses on the journey of belief formation rather than demanding justification.
The book emphasizes that even if you completely disagree with someone’s conclusions, you might find something in the path they took that you can relate to, like building base camps up a mountain that help you climb higher in understanding.
While Guzmán provides the process, the emotional work of choosing curiosity over certainty is the bridge builder’s alone.
“Look for the ones who are somewhere in the middle, for the people who are willing to be willing.”
Cassie and Terri’s friendship resists our current era’s demand for absolute certainty. Instead, it creates space to explore complexity even when the broader political ecosystem rewards simplicity and demonization. When asked about why so many of us now have a hard time having friendships across political ideologies, Terri reflected, “We’ve stopped communicating. We’ve all siloed. It used to be a lot more gray. Now you have to swear allegiance to one camp or the other.”
Rather than trying to convince the most entrenched voices, Terri and Cassie offered this advice: “Look for the ones who are somewhere in the middle, for the people who are willing to be willing.”
This is strategic wisdom about where to invest energy, especially when political and media incentives reward the most polarizing voices. As for boundaries, Hemphill writes, you can care about reaching people without exhausting yourself, which happens when trying to connect with those who profit from maintaining division.
Creating Nonpolitical Spaces
Shared activities create conditions where people can get to know each other as whole humans, rather than political positions. The Presidential Leadership Scholars program created the initial structure for Cassie and Terri’s friendship, but the principles can work anywhere—neighborhood associations, hobby groups, volunteer projects.
The key to designing spaces around a shared purpose rather than a shared ideology is recognizing that this work requires deliberate efforts to resist forces that benefit from our separation. (As mentioned in my last article, you may want to look into bowling.)
“There are people who would love to push us toward civil war,” Terri warned. “We had one, and we don’t need another one.”
Terri’s warning reminds us that maintaining democratic friendship isn’t just a nice ideal—it’s civic resistance against those who gain power through division. When political operatives and media figures benefit from keeping us angry and afraid of each other, choosing to stay curious about people we disagree with becomes a radical act.
The breakdown of a shared reality isn’t just happening in politics—it’s happening at family dinners, in workplaces, in faith communities. But the solutions are the same: it requires the patient work of building relationships across differences. It’s also about recognizing that democracy requires the ability to stay connected across differences, even when powerful interests would prefer us isolated, each of us in our respective camps.
As I left our conversation, I was struck by how ordinary Cassie and Terri’s friendship seemed, despite crossing what we’re told were unbridgeable divides. Building a shared reality with people we disagree with isn’t extraordinary political work—it’s ordinary human work, essential for democracy. The question isn’t whether we need these relationships. The question is whether we’re willing to do the work to build them, knowing that this work itself is an act of resistance.
