What Bill Maher Missed In His Meeting With Trump

The comedian was surprised the President was so charming in person—but that was the point.

Last week, Bill Maher met President Trump at the White House at an unlikely dinner date set up by Kid Rock.

Maher, a long-time Trump critic who was once sued by him for joking that he was "the spawn of an orangutan," shared the full play-by-play in a 10-minute book report on Real Time with Bill Maher Friday night.

I’m not sure what Maher expected going into the meeting, but his takeaway was one of genuine surprise and even admiration.

For all his years mocking Trump on air, he found the version of the guy he met to be an absolute delight.

“He was gracious and measured…He’s much more self-aware than he lets on in public.”

Maher has mocked Trump for never laughing, but apparently, this night, Trump yukked it up.

“He laughs! I've never seen him laugh in public. But he does, including at himself. And it's not fake. Believe me, as a comedian of 40 years, I know a fake laugh when I hear it. And I thank you for them.”

Maher was also shocked by how open Trump seemed to criticism.

When he told the President he thought scrapping the Iran nuclear deal was a mistake, Trump listened.

When Maher questioned parts of Trump’s plan for Gaza, Trump nodded and even agreed in some cases.

“I never felt I had to walk on eggshells around him…There were so many moments when I hit him with a joke or contradicted something, and no problem.”

In the end, Maher concluded he was somewhat confused by how the guy he met for dinner was the opposite of the guy we all see publicly.

“A crazy person doesn't live in the White House. A person who plays a crazy person on TV a lot lives there.”

Charmed and Disarmed

It was all kind of cringy. Not because Trump was a charmer, but because Maher seemed so taken in by it.

I mean, isn’t this what narcissists do? They put on the charm for the people they want to impress. They mirror your values. They laugh at your jokes. They make you feel heard.

It’s all part of the manipulation.

And even if Trump wasn’t trying to manipulate Maher, even if he was just Trump being Trump in his natural habitat. His behavior still reeks of narcissism.

For all his MAGA bravado and regular-guy posturing, Trump has always craved the approval of A-listers like Maher. He doesn’t just want to win; he wants to be liked by the people he publicly trashes.

Narcissists want to be in the room with the cool kids.

Approval from the masses is nice. But approval from the elite? That’s power.

How Do I Know This?

I’m not a therapist or a mental health professional, although I married one. So what makes me at all qualified to have an opinion about this?

Because I was in a cult for 15 years, and I can assure you this is exactly how cult leaders operate.

In my experience, the cult leader constantly criticized the materialism and shallowness of the outside world. He told us we were above it. That true enlightenment came from rejecting status and staying loyal to his principles.

But the moment someone with real-world success entered the picture, everything changed. The outsider was treated like royalty—invited to private dinners, lavished with attention, praised mercilessly.

The same man who preached wordly detachment would fall over himself to impress anyone with fame or money.

Meanwhile, the true believers—the ones who gave up everything to follow him—were mostly ignored. Second-class citizens funding his lifestyle.

And as soon as the celebrity left? He'd talk trash behind their back. Dismiss them as shallow, corrupt, unenlightened.

The cult leader wants it both ways: to pander to his base and impress his peers. To be worshipped and accepted.

Sound familiar?

It will come as no surprise if Trump talks smack about Maher in the next few days, especially if he thinks his MAGA base is losing respect for him.

And Maher will say, well, that’s the public Trump, the performative Trump. The Trump I met was really a decent guy, funny even.

This brings me to the next thing that really stuck in my craw.

The Big Deflect

Maher opened his monologue:

“What I'm gonna do is report exactly what happened. You decide what you think about it.”

And later, he ended by saying:

“OK, that's my report. You can hate me for it, but I'm not a liar… I'm just telling you what I saw, and I wasn't high.”

I liken this to Joe Rogan’s “I am just asking questions” defense.

Framing yourself as a neutral observer doesn’t absolve you from the impact of what you’re putting into the world, especially when your platform reaches millions.

Maher hasn’t gone full MAGA, and I fully expect him to keep mocking and criticizing Trump. But by stripping the night of context and letting Trump’s charm outweigh consequence, he does us all a disservice.

Would I have done anything differently? Probably not. Like so many before him and after him, Maher was swayed by an expert conman. Just as I was all those years in the cult.

Do I hate Maher or think he’s dishonest? Absolutely not. I will continue watching his show and agreeing with many of his observations.

However, let’s be honest here, Bill: There’s a reason Trump has gotten as far as he has. And it’s not just because he plays a strongman on stage. It’s because, behind closed doors, he knows how to work a room.

You’re a standup comedian, for Chrissakes, you know all about that!

Maher may have been “just telling us what he saw,” but what he saw was an act. And what he reported, unintentionally, helped soften the image of someone whose most damaging behavior happens in public.

He ended by saying, “I wasn’t high.”

But maybe it would have been better if he was. Because he was clearly under the influence of some other bullshit.