LOS ANGELES, CALIFORNIA - DECEMBER 02: Bill Maher attends a game between the Houston Rockets and ... More
Some images stop you mid-scroll.
For me, one of those was a photo of comedian Bill Maher—longtime liberal firebrand—having dinner with President Donald Trump, a figure he’s relentlessly criticized for years.
My first thought: Seriously?
My second: Good on him.
Not because I share all of Maher’s views (or President Trump’s), but because what we witnessed wasn’t just an unexpected dinner—it was a small but immensely potent gesture toward something we desperately need more of: dialogue across divides.
In an era of outrage—where even casual conversations can spiral into ideological standoffs—sitting down with someone you vehemently disagree with has become a radical act, one that risks marginalization or, at the very least, public condemnation. Certainly, many were quick to criticize Maher, accusing him of legitimizing Trump simply by sharing a meal. But the more constructive response, in my view, is to applaud his willingness to engage. Maher didn’t soften his stance or retreat from his convictions. As he later said on his show, “I did not go there to kiss the ring.” He pushed back—directly, respectfully, and with tough questions.
Maher, who has spent decades fine-tuning his brand of biting, socially charged humor to make sense of complex, often uncomfortable issues, brings a sharp wit that’s more thoughtful and layered than he’s often given credit for. Beneath the sarcasm and satire, there appears to be a genuine desire to challenge assumptions, expose hypocrisy, and shine a light on uncomfortable truths and double standards.
Will their ‘breaking bread’ shift any of Trump’s policies or perspectives? I wouldn’t bet on it. But that was never the point. The deeper value of their conversation lies in the act itself: two people with vastly different worldviews, sitting face-to-face in civil conversation—not to convert each other, but to better understand one another; to understand why someone believes what they do, and who they are beneath the labels, rhetoric, and public persona.
The Latin root of the word conversation is conversari—“to turn about.” That’s the potential of genuine conversation. Not to convert others to our views, but to soften our certainties. To walk away seeing the world just a little differently.
This is the hard work of bridging divides. And we need more of it.
Just last week, I led a bipartisan leadership session for Congressional Chiefs of Staff on Capitol Hill which I’ve been doing now for several years. It reinforced something I’ve seen repeatedly: the majority of people—on the left, right, and in between—genuinely want to work toward a better future, not fuel ideological warfare. But meaningful progress takes a special brand of personal bravery. It requires us to step out of our self-protective echo chambers—those places where our certainties are constantly validated and our (often unconscious) desire to claim the moral high ground is actively reinforced (and rarely challenged) —and into spaces where our entrenched perspectives can be tested, and our perspectives stretched.
Of course, like so many optimal behaviors, this is not easy or comfortable work. In fact, it’s just the opposite. As social psychology researchers have found, our brains are wired for certainty and belonging—often at the expense of curiosity and nuance. Echo chambers don’t just keep us comfortable; they keep us convinced. Convinced that we are right. And that they are not just misguided and wrong, but outright dangerous, even existentially threatening.
No, we won’t always agree. Some conversations will be awkward, tense, even painful. The most critical conversations often are. But we cannot bridge the divide by refusing to sit at the same table.
Abraham Lincoln once said, “I don’t like that man. I must get to know him better.”
That quote speaks to the essence of real leadership—not just the courage to speak truth to power, but to set aside tribal loyalties and listen to those who see the world differently. If Albert Einstein’s observation that "problems cannot be solved from the same level of thinking that created them”, then vilifying those who don’t share our views won’t rebuild trust, heal relationships, or unify communities.
What will?
The willingness to loosen our grip on our certainty and engage with those who trigger our judgments.
The humility to consider that maybe—just maybe—there’s something we haven’t seen, felt, or understood.
And the courage to see how someone else might be the hero in their story, even when they seem like the villain in ours.
I don’t see how we move forward without more of that kind of courage.
If a president and a comedian—two men who’ve traded barbs for years (Maher walked into the White House with a full sheet of Trump’s insults… which Trump promptly signed)—can sit down for a civil conversation and break bread as two humans with something to learn from each other, maybe the rest of us can too. And maybe—just maybe—that’s where real change begins.
It’s easy to throw stones. Far harder is using them to build a bridge. But in this moment, that may be the most important work of all.
Margie Warrell, PhD, is a leadership speaker, advisor and bestselling author dedicated to bridging the courage gaps that confine people, leaders, organizations, and our shared future. Her latest book is The Courage Gap. More at www.MargieWarrell.com.