I dive into a challenging interaction I had during a live call-in segment, which left me feeling both frustrated and intrigued. The core of the conversation revolves around the concept of radical skepticism, a philosophical stance that questions the possibility of certainty in knowledge. I reflect on a personal experience with my brother, who was influenced by a radical skeptic he worked with, and how that impacted our family discussions about reality and communism. I recall the outrage my mother expressed during a debate about whether the existence of a purposeful divide, such as the Iron Curtain, could imply a hidden paradise behind it—a striking illustration of how radical skepticism can distort clear thinking.
The episode also highlights my struggle to maintain composure and clarity during live debates, especially when faced with callers presenting bewildering arguments. I share my introspection on how I performed in this debate, giving myself a self-assessment and discussing potential improvements. The challenge was not just the argument itself but the underlying implications of doubt and the mental gymnastics involved in navigating a conversation with someone deeply ensnared in skepticism. My goal is always to articulate the importance of distinguishing reality from fiction, yet this debate served as a reminder of how easy it is for insanity or manipulation to creep into philosophical discussions.
As I unpack my opponent's claims, particularly their assertion that certainty is unattainable, I encounter logical pitfalls that reveal the absurdity of their position. The lack of a shared understanding becomes apparent, as radical skepticism twists the basic principles of conversation. I contemplate the implications of engaging with such arguments and the responsibility I feel to protect my audience from potentially harmful ideas that could undermine their grasp of reality.
Additionally, I consider the emotional toll these discussions take and how they can feel like a mental assault, warping the very foundation of understanding. The episode becomes a case study in not just debating ideas but in understanding the psychological landscape of skepticism and the fear of certainty that often accompanies it. Drawing on historical examples and personal anecdotes, I aim to foster a clearer vision of reality amidst the chaos of competing philosophies.
Ultimately, I seek feedback and thoughts from listeners on how to improve my approach to such radical skepticism in future discussions. It’s an ongoing challenge—and a vital conversation—about the nature of belief, truth, and the philosophical battles we navigate in our search for understanding. This episode invites listeners into a deeper reflection on what it means to engage with uncertainty and how to defend against the encroachment of nihilistic thinking in everyday discourse.
0:03 - Introduction to Radical Skepticism
3:18 - Personal Experiences with Skepticism
6:20 - The Assault on Reality
12:08 - The Nature of Mental Assault
15:21 - Debating the Undebatable
18:17 - The Relationship Between Certainty and Abuse
22:11 - The Impossibility of Conversation with Skeptics
22:44 - Conclusion and Call to Action
[0:00] So it is October 23rd, 2025. So yesterday we had a caller, a call in, obviously, to the Wednesday Night Live. And it left me pissed off and jangled. Honestly, and I know why. It actually, this is just for donors, right? So I can get a little personal. But it's because this radical skepticism is my brother. And I remember my brother, worked up north and had someone he worked with who was a radical skeptic, who really did a number on his brain. And I remember him saying, my brother saying, well, how do you know that the Iron Curtain or the wall that keeps West Germany from East Germany is not there because.
[0:57] East Germany or the East German part of Berlin is a paradise and it's to keep you out of this amazing paradise. I just want to sort of just radical skepticism, right? Well, how do you know? How do you know? Could be that it's paradise over there and the wall is just to keep people out, right? Away from paradise. And my mother was really angry and upset. I remember this debate very clearly. I'm trying to think of the ages. I would have been maybe 16 or 17. My brother was a little older, of course. And I remember my mother being outraged and angry that my brother would make this case. And I mean, I guess you guys know, if you know about my history, you know enough about my history to know that if I'm saying my mother was the sane, rational, moral force in this conversation, uh, you know, that's saying a lot.
[1:54] That's saying a lot. That's saying a lot, to put it mildly. Yeah, I remember we had these sort of fuzzy green couches that were corduroy, that were L-shaped, and my brother was home from working up north, and my mother was over, and he was making this whole case about how, how do we know communism could be the best system ever? And we don't know for sure. We've never visited. Could it all be propaganda? Maybe all of the propaganda about communism is just made up and so on, and maybe the wall is to keep us non-communist out so that they can have their perfect communist system, you know, that kind of stuff, right? And of course, I didn't really get it as much. I knew that my mother, of course, was born in Berlin in 1937.
[2:37] So I knew that she was, you know, pretty intense about this topic. Now, of course, I didn't understand back then because it was only much more recently that I began to learn just about the horrifying treatment of females by the Red Army at the end of the war. So when my brother was saying communists, you know, how do you know the communists aren't the good guys? Communists could absolutely be the good guys. Well, you know, my mother was treated appallingly in ways that I think Satan himself would quail before after the war. So I'm not blaming my brother for this. He didn't know this history either. It's pretty well suppressed, right?
[3:15] But I think that's one of the reasons why it bothered me. And the other thing too, you know, it's a pretty wild thing to have a debate that kind of comes out of nowhere and people are, you know, really kind of in system.
[3:32] I know, I mean, I'm basically dialing up to, I think I'm one of the few people left who does live shows, live debates, no prep, right? I mean, I'm not prepared for these topics as a whole. Like, I'm not prepared for the guy who calls in trying to defend CP. I'm not prepared for, you know, guys who call in sort of radical skeptics and so on, right? Now, if I know I'm going to have a debate, then I can do the research and get my arguments ready and so on. But that's fine. I mean, I know that that's the nature of the beast. It's not an excuse. I'm just saying that it is sort of an interesting environment to be in. So, I would give myself 7.5 to 8 out of 10 in that debate.
[4:17] It's a passing mark, but it's not a great mark. A 9 or a 10, obviously, is the ideal. I would give myself probably a bit closer to 8, but 7.5. I'd give myself, let's say, 78% on that debate, which is good, but not great, and certainly not a knockout.
[4:40] So, in reviewing how I could do it better, how I could improve, and it's funny because I said at the beginning, what are the arguments, if I'm going to debate with someone, I need to ask them, what are the arguments against your position? Have you studied the arguments against your position?
[4:53] Now, I did that, of course, because I said to, I'll just call him Bob, right? I said to Bob, have you read Essential Philosophy? Yes. Well, what are my arguments? Well, I just kind of skimmed it. And personally, I think he's lying. I just, I don't think he's read it. I think he's, yeah, I've read it. But he, you know, I just skimmed it, you know, that's what people who haven't done their homework do, right? They just, yeah, yeah. But, you know, I just kind of, I didn't read it in great detail, blah, blah, blah. Did you remember any of the arguments? No, oh, it's like it was a while ago, I just skimmed it. Yeah, so anyway, so then there's no functional difference between reading and not reading the book. And early on, of course, and it was interesting because he was saying that he wanted to apologize, but then he wouldn't say anything that he had to apologize for. And I don't know, part of me was like, I should stay on this topic. And the other part of me was, does that sort of open your flank to like, well, just let it go. He apologized. What are you hammering him for? And the sort of peanut gallery and so on, it's something that I have to sort of be aware of because I'm not debating in private. I'm not debating in some sealed Oxford Union demons, right? So I have to be aware of sort of the peanut gallery and what they're going to say and think. But I did kind of move on and let that one go, which I thought was I think it was okay, because it was interesting to get to the other debate.
[6:20] I view what Bob was debating or what he was arguing for, I viewed it as an assault.
[6:29] And I do, honestly, just straight up, I do view it as assault. And I sort of tell you why. So, if you were to go to your doctor and you were to say, I don't believe anything is real. I don't believe that you're real. I am not certain that this table exists. I don't know if the world exists. I don't know if I'm just wildly hallucinating or if anything is real. And you genuinely believe this, right? What would your doctor do or say? A, I don't know, but B, if I had to guess, your doctor would probably suggest that you go to a mental health facility, that you check yourself into some mental health facility. Because people who are unable to distinguish reality from fantasy are psychotic.
[7:26] Psychotic is someone who's unable to differentiate reality from fantasy. They see dragons, they see fire in the sky, they see giant buses that look like snakes. They're in a waking dream. They don't know reality from fantasy. That's the beautiful mind thing, right? So, if being unable to differentiate reality from fantasy, objective from subjective, is a mental illness that is serious. It's very serious.
[8:01] Well, I'm going to assume that reality is real, but I don't really believe it. I can't prove it. I don't know for sure. I'm not sure. Sure about anything. I don't even know that two and two make five, blah, blah, blah, right? Or you get to these sort of rank contradictions. And this is where the sort of sanity thing is. So I asked the guy, like, is there any point where you cross a line and you say, okay, well, what I'm saying really doesn't make any sense. Like when he was saying, you can't prove that a pizza without mass doesn't exist, right? I mean, there's so much that's wrong with that sentence, right? You can't prove that a pizza without mass doesn't exist. Well, anything without mass by definition doesn't exist. Non-existence is the absence of mass. So by definition, a pizza without mass doesn't exist. The other thing too, is that a pizza without mass is a contradiction.
[8:56] Pizza without mass is a contradiction. Because a pizza exists. That's why I said if you get the open box, do you still pay for the pizza? Well, of course not, right? So a pizza without mass is non-existent and shares that characteristic of non-existence with everything else that doesn't exist. Like if I were to say, the space between the stars is filled with pizzas that don't exist. Of course, the question would be, well, why would you categorize something that doesn't exist as a pizza, right? And there was an escalation, right? And I viewed him like a flamethrower, like somebody who was spreading psychosis through the insistence of his language. So, when somebody says, you can't prove that a pizza with no mask doesn't exist, again, to unpack what's wrong with that, if it's not obvious. And look, I get, you know, we want to take the non-obvious and break it out and all that kind of stuff. How do the senses operate and things like that? We want to do all of that for sure.
[10:03] But if someone says, you can't prove that a pizza with no mass doesn't exist, the question is, and this is, it's not an argument, I get that. But if somebody doesn't notice that that's insane, like, I don't mean it's always kind of crazy, like, that's insane. That's insane. In the same way that if someone serves this guy a pizza, Joe serves Bob a pizza, box, right? And he wants to order a pizza and it's in a box. And then Bob opens up the pizza box and says, there's no pizza in here. And Joe says, you can't prove that there's no pizza in there. You sort of wave your hand in there like there's no pizza. You can't prove that there's no pizza in there.
[10:49] That is either, it's either A, insane or B, fetishistically manipulative. Like it's so deeply committed to being fucked up and manipulative that it's either insane or utterly corrupt. An assault upon reality right if you were to take a pill right this is right this is why i fought so hard with this guy right so if someone were to force feed you a pill that had you unable to tell what was real and what was not real i mean you couldn't leave the room like in other words if someone sent if someone fed you a pill in your bedroom and or someone drugged your drink and then And what they did was, you woke up and you couldn't tell the real from the unreal. You couldn't tell if you were in a waking dream. You couldn't tell if you were awake or asleep. You couldn't find the door because the door kept opening and closing like a mouth. It kept drifting all over the place. It turned from a door into a doormouth, into a dormant bear, right? It would just keep changing. It would be on the ceiling. something like you would consider that one of the worst conceivable assaults on your mind that would ruin your entire life that you would have to go through life not able to trust any of your senses.
[12:09] And hallucinating now he would say yes but but i don't hallucinate blah blah blah but not being certain right i think that's a door that i can go through i'm not sure it could be a door i go itself, right? I don't know. To not be certain.
[12:28] So, in terms of how to handle the debate better, you know, it's a tough thing because philosophy should be able to handle just about anything. Philosophy should be able to handle just about anything. And so, if someone says, I'm not real, you're not, somebody says, you're not real, I know two and two don't necessarily make four, blah, blah, blah, then can you handle it? Can it be done, right? Because if I just kick the guy and say, if you don't believe that two and two make five, I'm not going to have a debate with you because you're insane. Does that feel like a cop-out? Because there's a lot of people who have that kind of perspective. I view it as a dominance play, basically, because he got very huffy when he perceived that I was talking over him, which I was at times. It was not just a perception, right? I was talking over him at times for sure. But then he was certain that it was negative, right? It was bad. Well, you talked over me. It's like, so? Well, you don't even know that two and two make five. What does contradictions matter, right? So, what do you do when somebody launches into that? Now, I need to be able to defeat.
[13:37] Virus. I need to be, because if I'm going to allow the virus of doubt to land in the mind of my audience, I have to be the antibody, right? That makes sense, right? I have to be the antibody against the virus. I can't just let it infect people and then hang up on the guy, right? Because then it'd be like, wow, Stef really ran away from that debate. Maybe he's scared. Maybe he doesn't have the answer. Maybe it's all bullshit. Maybe the other guy, do you know what I mean? So there's a dominance play that comes in, which is you can't be certain of anything. You can't be sure of anything. Okay. And of course, I asked him, are you certain you can't be certain of anything, blah, blah, blah. And that just kind of faded out. And it's not the greatest answer in the world. I mean, it's an interesting kind of logical hiccup, but it's not the greatest answer in the world to, I'm not certain of anything. Are you certain of that? I mean, it shows a contradiction, but it's the only thing I'm certain is that I'm certain of nothing, blah, blah, blah. Okay. I mean, you can, it's not, it's not hugely compelling. It's not bad and it's interesting. And it's definitely a pushback, but it's not compelling, right? So what should I have done in hindsight, right? How could I have handled it better? I mean, again, I think I did a pretty good job, but I could have done it better. I don't know for sure because people who are either insane or this guy wasn't insane, but he was attempting to spread insanity. He was a a mental virus, in my view. But this guy was not insane.
[15:03] So he says, I don't know anything for certain, right? What if the response is to just not engage? And he says, don't you have anything to say? And I said, I already gave my reply. He says, oh, I must have cut out. I didn't hear it, right? Then he says it again.
[15:22] And I say, no, no, I already gave my reply. And he's like, "'No, you didn't.' "'Yeah, I did. "'I gave my reply. "'No, you didn't. "'I didn't hear anything.' "'Are you certain?'.
[15:35] That's the approach, which is to take the principles of the debate as his principles as axiomatic to begin with, right? So maybe what I can do is I can say, okay, let's have the debate on radical skepticism as if we're both radical skeptics. So I can not give a response and then claim I gave a response. Or he can say, I'm not sure that two and two make five. And then I can say, so you're saying that two and two make four. Sorry, he says, I'm not sure that two and two make four. And I say, oh, so you are certain that two and two make four. You're a hundred percent said, no, no, that's not what I said. How do you know? Well, it's recorded. So we're certain, right? So maybe instead of cheesecake without dairy, blah, blah, blah, right? Non-dairy cheesecake, which is that cheesecake? I mean, and I get, you know, he had a reasonable point about that in terms of semantics. I mean, that's fine. That's why I moved to said, okay, fine, let's take another example.
[16:36] But maybe it's better to take the premise of the argument and to say, I can either do it verbally or I can do it empirically. So I can either verbally say, okay, so if you're not sure that two and two make four, how can we have a debate? Well, because of X, Y, and Z. It's like, well, I don't know if I heard X, Y, and Z. I'm going to take your approach and accept radical skepticism. I'm going to take your approach. And then if I get things wrong and he corrects me, he's violating radical skepticism. Because he's going to say, I said, I couldn't be sure if two and two make four. And I would say, so you're certain that two and two make four. It's like, no, that's not what I said. How do you know? Well, I know what I said, right? Know what my reply is, my reply, right? So, or if somebody says, yeah, so it's a meta question or a meta narrative, which is to say that how can you be sure of anything if you're going to have a conversation? Because he wasn't certain that I existed, but he wanted to call back. Now he's going to say what he's going to say, right? Because he's going to get the best of both worlds. so maybe this wouldn't work. Because he's going to say that...
[18:01] As if things are real, even though I cannot prove that they're real. I'm going to act as if they're real, although I cannot prove that they're real. And then he gets the best of both worlds. So he can be certain about things, but he gets to retain his skepticism, right?
[18:18] Yeah, it's funny because I can feel that a little bit of churning in my gut, this like mental assault, right? And honestly, I mean, I really do think that this is going to be more important in the long run than the political stuff that I did. Or even, God, what was it? My producer put together a presentation on David Letterman after we had success with Robert Williams, which went precisely nowhere. You can't reproduce success. It's just a fact. So maybe somebody says, I can't be sure of anything, and I'm just silent. Or just let them talk. The problem is, what do I do if that person just keeps on talking. And then I'm letting them communicate their mental sickness, their corruption to my audience. So that's a problem, right? So let's say he just rambles, right?
[19:10] Then I'm letting him infect my audience. If he just keeps spewing all this crazy shit, right? I'm letting him infect my audience. Maybe I just don't like, he apologizes, I don't respond, right? I don't respond. And then he says, don't you have anything to say? And I say, how do you know I didn't say anything? Oh, maybe that's it. Maybe this guy's like, I'd like to apologize. I just don't answer. Are you there? I don't answer. Don't you have anything to say? I did say something. I did reply. Oh, there must have been a bad connection. Okay.
[19:43] Oh, it must be a bad connection. Okay. And maybe that's it. And then just hang up with the guy and then say, well, how did he know? How did he know I didn't reply? Or how did he know I did or didn't say anything? Because I really find it annoying when people push all of this supposed certainty and then whenever confronted on absolutes, it's the pause, you know, this pause, it's just, it's a mental chasm or a canyon, which is, you know, is it more accurate to say that the sun is the center of the solar system or that the earth is the center of the solar system?
[20:18] Like the pause, right? Isn't it kind of a paranoia? It's a paranoia, isn't it? Like, I can't, at the moment, I'm certain I'm going to get attacked. The moment I'm certain I'm going to be abused. The moment I'm certain I'm going to be humiliated. The moment, right? So there's this fear of certainty, which turns into an attack upon certainty, right? There's a fear of certainty that turns into an attack. And I assume it's because they were abused by somebody who was absolutely certain that they were right and this guy was wrong and beat him senseless or whatever it was, right? So then certainty becomes abuse. And then your defense against the abuse called certainty is this sort of radical skepticism. So I would say skeptical compared to what? And I was sort of doing that at the beginning, but I think I, I wouldn't say I got dragged because, you know, it's a choice, but, you know, trying to move with the debate. I was saying, you know, well, we got rid of the earth is flat and went with the earth is round because the earth is round, right? So it's closer to the truth, right? But you can't ever get there. It's an asymptote. You can get closer to the truth, but you can't get the truth, right?
[21:24] I just need to not respond, let them get more frustrated, and say, I did respond. No, you didn't. Are you certain of that? Well, I'm mostly certain. Then how dare you accuse me of not responding? Yeah, I think maybe that's it, right? They ask a question. I don't respond. They say, are you still there? And I said, I just gave you an answer. And they said, no, you didn't. Ah, there you go. You're 100% certain that I didn't. Boom, we're done. You didn't say, I'm somewhat certain, or I don't think you did, or whatever, right? You just said, no, you didn't. Well, that's just a convenience. Nope. The moment you make an absolute statement, you can't be a radical skeptic anymore. Or if they say, I don't even know that two and two make five, I can say, I have no idea what words you just used. I don't know what words you used. I can't have a conversation. Well, I said that two and two make five. I don't know that.
[22:12] I mean, I think maybe, but I don't know. So I think maybe that's the approach to take, is to simply point out the impossibility of a conversation with someone who is a radical skeptic. That they don't even know if you answered or haven't answered. They don't have any knowledge of any particular meaning of the words. They don't even know if you exist. And so maybe the problem is that I graced
[22:36] someone with the sobriquet of rational or debate-worthy when they just plain weren't. Hope that helps. Love to know what you think. Freedomain.com/donate. Well, you guys are subscribers anyway, but hey, never hurts. Bye.
Support the show, using a variety of donation methods
Support the show
