What are the patterns of civic engagement that we need for a healthy representative democracy? What is required of the citizens represented—individually and collectively—for it to be successful? What, if anything, can philanthropy do to help cultivate this kind of citizenship, when by its nature it is diffuse and subject to myriad social factors that encourage or work to undermine it?

We have been wrestling with these questions from the outset of the Madison Initiative. Last week they were again brought to my attention as I read Marc Dunkelman’s compelling new book, The Vanishing Neighbor: The Transformation of American Community.

I won’t be able do justice here to the full sweep of Dunkelman’s creative synthesis, in which he brings together many varied strands of wisdom— from Robert Putnam’s Bowling Alone and Theda Skocpol’s Diminished Democracy to Bill Bishop’s The Big Sort and Eli Pariser’s The Filter Bubble, to sample just a few. All the while Dunkelman is weaving in his own powerful insights.

At the heart of Dunkelman’s argument is the importance of what he terms “middle ring” relationships. These can be defined in part by what they are not —neither the “inner ring” relationships of one’s nuclear family and close friends, nor the “outer ring” relationships that are “passing to transactional,” a result of “a single shared interest or experience.” By this he means professional acquaintances, but also social media connections with far flung people who happen to share your passion for, say, Patsy Cline, the Detroit Tigers, Friedrich Hayek, or unstinting environmentalism.

Middle ring relationships, in contrast, are “familiar but not intimate, friendly but not close.” Think here of the talkative neighbors who always buttonhole you when you are walking your dog, fellow members of the Kiwanis Club, the parents of your children’s classmates with whom you arrange the weekly carpool, the “regulars” you have lunch with in the cafeteria at work, the other members in your National Guard unit, and the guys who play in your standing Tuesday night pickup basketball game, etc.

If you’re having trouble identifying with these examples, you may be seeing Dunkelman’s point by now. Our middle ring relationships are atrophying, and the social consequences are profound. “Today, if you don’t know your neighbors—if you’ve transferred social capital away from the middle rings—your political frame of reference is limited both to the people you love most and the legions who, through outer-ring networks, share your point of view.”

The problem is that middle ring relationships have, from the era of Alexis de Tocqueville’s townships to that of Jane Jacob’s front stoops, formed the basis for our political community. Middle ring relationships are where we are most likely to rub elbows with people who may not always agree with us yet we cannot avoid, where we come to appreciate that at times you need to go along to get along, where we learn informally to lead—and to follow. These relationships are primary school for citizenship, and we’ve become truants.

Dunkelman connects the dots between the demise of the middle ring and the mounting problems of our nation’s politics. “Absent the fundamental ability to understand those on the other side of a cultural or political divide, it’s almost impossible to stomach the possibility that “our” representative in Washington might be the one collaborating with people who represent a different flavor of constituent.” The art of compromise—as essential to governing in the halls of Congress as it is in city halls in Paducah or Poughkeepsie —has thus become a dirty word. “The institutions that frame American society no longer line up with the routines of our daily lives.”

To his credit, Dunkelman doesn’t leave us with pat answers or solutions to this dilemma. He doesn’t suggest that we can somehow go back to the patterns of citizenship that Tocqueville or Jacobs observed and celebrated. Rather, he challenges us to adapt our institutions to the social changes that have been disrupting them, and to explore ways in which we can put our evolving networks and relationships in harness so that we can better govern ourselves. Friends, neighbors, citizens: We’ve got our work cut out for us!