There are easier ways to spend a Tuesday night in Sarasota than discussing politics with strangers. Sure, some choose to do so from the comfort of their couch and behind the safety of an ambiguous Facebook profile picture. But for many, sitting face-to-face with people whose views differ from your own sounds like a recipe for elevated blood pressure and regret.

And yet, at meetings of Conversations Across the Aisle (CATA), dozens of people regularly opt to do that. The man responsible for convincing them this is a good time is CATA’s founder, Bill Woodson. He knows it sounds ambitious. "Everyone thinks their thing is going to save the world," he says with a laugh. "I'm not sure about the world, but I do think [listening and talking] can help save the United States."

CATA operates on a surprisingly old-fashioned premise—people are more likely to understand one another if they sit down together, share a meal and have an actual conversation. Participants sign up in advance for topics from the separation of church and state to whether education is still a public good. They eat dinner together, hear a neutral presentation from an expert on the issue, and then, sitting at tables, talk to people who may see the world very differently than they do. The goal isn't to win an argument—it’s pretty much the opposite.

"People don’t want their minds changed,” Woodson says. “The key criteria that qualify someone as a good person to join a CATA community are that they have authentic curiosity about how different people think differently about these issues.”

Long before he began encouraging conservatives and progressives to share a table, Woodson built a career translating ideas between people with differing points of view. As a budget analyst, computer programmer analyst and, later, a marketing professional working alongside engineers, he repeatedly found himself serving as a bridge between groups with different priorities and assumptions. “This notion of trying to get people to be on the same page to understand each other is a connecting thread throughout my career,” he says.

CATA’s first workshop was held in October 2023, after Woodson and a team of volunteers spent nine months developing a format that borrowed and built on successful elements from other dialogue-focused programs. Since then, the organization has grown, attracting hundreds of participants and expanding beyond Sarasota to Lakeland and Venice. Even cities in other states, like Texas, have expressed interest in developing their own CATA community, and there are plans to bring the project to younger populations as well.

That growth suggests a hunger for something many Americans say they want but rarely practice: meaningful conversations with people outside their own ideological bubble—bubbles Woodson believes are doing real damage. “You turn on CNN, and they’re antagonistic to the administration. You turn on Fox News, and the administration can do no wrong,” he says. “On social media, the people getting the most clicks are the ones with the sharpest takedowns and the harshest attacks on the intellect of the people they disagree with.”

The result is a culture where people increasingly make assumptions about one another without ever having a conversation, becoming so defensive and distrustful that sharing a room with someone on the other side can feel unthinkable. "It's hard to care about people that you can't even have a conversation with," Woodson says.

For him, that may be the most important lesson CATA offers. Participants don't always leave agreeing with each other, but that's never been the point. What changes is that they leave with a more nuanced—and often more compassionate—understanding of the person sitting across from them. In a time when disagreement often feels like a dead end, Woodson is betting that it can be a starting point instead. It’s a wager worth making.