Last Thursday I spent my evening in Boston’s North End, which was overrun by joyous Scots in kilts celebrating the World Cup. As The Free Press’s head of community and events, I’ve spent the last few months helping build the Free Press Supper Club, a new dinner series connecting subscribers for real-world conversation over shared meals. And on Thursday, I finally got to attend one.
Our table was upstairs at the Union Oyster House, away from all the ruckus. Within minutes, I found myself sitting with a perfectly Free Press mix of people: the writer and policy analyst Leor Sapir; a couple who found The Free Press through our limited podcast series The Witch Trials of J.K. Rowling and have been hooked ever since; an HR director for a Boston dental company who relies on The Free Press to challenge his assumptions; and a bond trader who argued that it’s our civic duty to speak up against ideological rigidity.
Needless to say, there wasn’t much small talk.
We went straight into Olivia Reingold’s reporting on anti-Israel sentiment in my home state of Vermont. From there, the conversation widened to Title IX, public schools, parenting, and whether the country is really as fractured as it feels.
And that was just our table.
While I was at one table in Boston, more than 2,000 Free Press subscribers across the United States, Canada, and Israel gathered at nearly 300 tables to do something increasingly rare: sit down with strangers and have an open, unfiltered conversation.
After dinner, nearby tables converged at after-parties. At a cocktail bar in Boston, a woman from Israel told me she came partly for conversation, but mostly in search of love. People exchanged phone numbers, and WhatsApp groups sprang to life on the spot.
All of this grew out of a project we launched less than a month ago: a new world of community experiences designed to bring Free Pressers together. Alongside the Supper Club, we launched The Free Press Forum, a digital community where thousands of readers have discussed the Iran war, the rise of socialism, books worth revisiting, political primaries, and plenty more. You’ve also welcomed newcomers, offered wise advice, made wedding dress recommendations, and, most remarkably, required very little moderation. Then you started asking for something else: a way to meet each other in real life.
At a moment when we’re constantly told Americans are retreating into tribes, 2,042 people volunteered to spend an evening with complete strangers and speak freely. I’ve spent the last few days looking through photos from the dinners in The Free Press Forum’s Neighbors channel, reading Forum posts, and thinking about the conversations I overheard that night.
What I keep coming back to is this:
Most of us know what it’s like to tiptoe around the subjects that matter most. It can be lonely. Last Thursday, we stopped tiptoeing. At our table—and at hundreds of others—we asked questions, challenged assumptions, and talked openly about topics that are the third rail elsewhere.
It’s easy to forget how good that feels.
If you missed out on the fun, don’t worry! Our next Free Press Supper Club is July 15, and we’re expanding from 28 to 39 cities. The theme is America at 250—we’re throwing birthday dinners for the country, Free Press style.
If you’d like to join us, reserve your seat now. Last month’s dinners sold out quickly, and July is already filling up!
The Free Press has always believed that adults can handle complexity—and each other. Last Thursday, you showed up looking for just that. And we’re just getting started.
The Free Press Supper Club and The Free Press Forum are available exclusively to paid subscribers. Upgrade today.
See you in July.
How about a supper club in London UK?
How about something in the Valley? LA is quite difficult to get in and out of on a weeknight.