It was a brisk evening in New York City, the kind of cold that had everyone bundled up and looking for a warm spot to take refuge from the sharp wind. But inside a luxurious steakhouse, the atmosphere was… shall we say, heated. Bill Maher and Donald Trump had agreed to share a meal, an idea that, in hindsight, no one—especially the two of them—would ever have considered a good one.
The table was set for two: polished silverware, crystal glasses, and a bottle of expensive wine that neither of them seemed interested in. Maher, ever the sardonic observer, couldn’t help but think how fitting it was that they were both seated under an oversized portrait of a smiling George Washington, looking like he was silently judging them both.
Bill Maher having dinner with Donald Trump. It was a terrible idea
Bill Maher, the self-proclaimed “liberal firebrand,” was uncharacteristically silent at first, staring down at the menu as though it were a crossword puzzle. Meanwhile, Trump, with his signature combo of self-confidence and casual arrogance, sat across from him with a grin that could only be described as “predatory.”
“Nice place,” Trump said, his voice booming like he was addressing an audience of thousands instead of just one person. “You know, I know the owner. He’s a great guy. Great steak.”
Bill Maher half-laughed, half-sighed. “I bet you do, Donald. You seem to know everyone.”
“Well, I do,” Trump replied, clearly delighted by his own observation. “People love me. They love the Trump brand. I built an empire.”
Donald Trump
Bill’s eyebrow arched, the subtle smirk on his face betraying his skepticism. “Yeah, you sure did. An empire of bad haircuts and gold-plated toilets.”
Trump leaned in slightly, narrowing his eyes. “You don’t like gold toilets, Bill? You know, if you had a little class, you’d understand.”
“Class?” Bill chuckled. “You’re like a walking billboard for excess. How’s your… what is it, a new hotel? Is it still mostly empty? Must be tough having all that space with so few people who can stomach the décor.”
Trump shrugged as though he were impervious to the insult. “It’s called luxury, Bill. Some people just don’t get it.”
“Yeah, well, luxury’s not exactly the first word that comes to mind when I think of you. More like… ‘pretentious’ or ‘oversized ego.’ But hey, maybe that’s just me.”
After ordering their food—Trump insisting
Trump didn’t flinch. Instead, he picked up his menu, waved it around, and dismissed the entire conversation with a half-hearted, “You’ll come around eventually.”
The waiter arrived just then, and the momentary distraction didn’t last long enough to break the tension. After ordering their food—Trump insisting on the most expensive cuts of beef, Maher opting for something more modest—the conversation turned, as it often did with these two, to politics.
“So, Bill,” Trump began, leaning forward again like he was about to drop a bomb, “You’ve been pretty vocal about me. I mean, I get it. You’ve got a show, you’ve gotta keep people entertained. But why so personal? Why so angry?”
Bill leaned back in his chair, crossing his arms. “I don’t know, Donald. Maybe because you spent years telling people that you could do whatever you wanted, that the rules didn’t apply to you. I’m a comedian. My job is to hold up a mirror to the absurd. And you? You’re the definition of absurd.”
People respect you?
Trump’s face reddened, and Bill could practically hear the gears turning in his brain, struggling to come up with a retort that wouldn’t make him seem weak. “I was the best president, Bill. The best. And everyone knows it. People love me. People respect me. You just don’t understand that.”
Bill’s lips twisted into a mischievous grin. “People respect you? I think you’re confusing fear with respect. They’re not the same thing, Donald. I mean, half of the country can’t even stand the sound of your voice, let alone respect you.”
The tension at the table was so thick, you could cut it with a butter knife. But Trump, true to form, wasn’t about to back down. “You know, Bill, I think you’re just jealous. I have something you’ll never have: power. People listen to me. I’ve got the kind of influence you can’t even dream of.”
Bill stared at his steak, then back at Trump
Bill leaned in, his tone mockingly sympathetic. “Yeah, because that’s really what we all want—more influence from a guy who thinks ‘the Art of the Deal’ is a strategy for running a country.”
By now, both of them were practically daring the other to make the first move in an all-out verbal war. A few minutes passed in uncomfortable silence before the food finally arrived, but the meal did little to ease the palpable animosity between the two men.
As the plates were set down, Bill stared at his steak, then back at Trump, and said, “You know, Donald, you might actually have a decent cut of meat here. Too bad it’s marred by all the grease of your ego.”
Trump picked up his fork, completely unfazed. “At least I’m not a self-loathing liberal with a deadpan sense of humor.”
Deadpan? More like napalm
Bill’s eyes twinkled with mischief. “Deadpan? More like napalm. But you keep doing you, Donald. I mean, you’re a gift to late-night hosts everywhere.”
The dinner dragged on like this, each passing moment feeling like a slow-motion car crash of egos. By the time dessert came—Trump declaring that he was too full for anything more than a “light bite” (as if that wasn’t just another flex)—Bill had made it his mission to get in as many jabs as possible, each one laced with humor so biting it could’ve given anyone whiplash.
When the check came, both men eyed it like it was a grenade.
“I’ll take care of it,” Trump said, tossing a couple of hundred-dollar bills on the table with a flourish. “It’s the least I can do for a guy who’s probably never had a good steak in his life.”
Bill’s eyes flickered to the cash and then back to Trump’s face. “No, no, Don, I insist. This one’s on me. You can afford it.”
As they parted ways outside the restaurant, the cold air felt almost refreshing after the warmth of their verbal sparring. Bill Maher was pretty sure he’d just had one of the most excruciating meals of his life—and Donald Trump seemed just as convinced he’d won the night.
But in reality, neither of them had won. Both left with their egos bruised, neither willing to admit that maybe… just maybe… the dinner had been a terrible idea.
