Welcome back to another Question of the Week here at The Confusing Middle! For those of you joining us for this weekly exercise in discomfort, I dig into Gregory Stock’s The Book of Questions every Saturday and share whatever psychological torture he’s cooked up for us. We’re now at week 469 of this journey, and Stock continues to find new and creative ways to make us squirm.

This week’s question: An eccentric millionaire offers to donate a large sum to charity if you’ll step naked from a car onto a busy downtown street and walk four blocks before getting back into the vehicle. If you knew there’d be no danger of physical abuse, how big a donation would it take to get you to do it? What if you knew your stroll would be posted online?

Well, Gregory, I see we’ve moved from contemplating our mortality to contemplating our dignity. Progress? I’m not sure, but at least this week’s question won’t keep me up at night wondering about my genetic predispositions. Instead, I’ll be lying awake imagining the horrified faces of innocent downtown pedestrians. So… thanks for that variety, I guess?

The Emperor’s New Donation

Let’s start by acknowledging what this question is really asking: How much is your dignity worth, and can it be measured in charitable donations? It’s like a twisted version of The Price is Right where instead of winning a new car, you’re losing your clothes and your self-respect, but hey, at least the local animal shelter gets a new wing.

The setup itself is fascinating. We’ve got an “eccentric millionaire,” which is apparently the polite way of saying “person with too much money and not enough hobbies.” This person has decided that the best use of their wealth is to create a real-life game show where regular people humiliate themselves for the greater good. It’s philanthropy meets public humiliation, charity meets comedy, altruism meets… actually, I’m not sure altruism is anywhere near this scenario.

The Hard No

Let me be crystal clear about my position: I wouldn’t do it. No amount of money would get me to take that stroll. The millionaire could offer to end world hunger, cure cancer, and fund a mission to Mars, and I’d still be firmly in the “thanks but no thanks” camp.

Now, I know what you’re thinking. “Aaron, don’t you care about charity? Don’t you want to help those in need?” Of course I do. But I also care about not traumatizing innocent bystanders who are just trying to grab their morning coffee. Trust me, I’ve seen me naked, and I’m doing everyone a favor by keeping that situation contained to my bathroom and the occasional unfortunate mirror encounter.

In fact, I’m pretty sure if an eccentric millionaire saw me naked, they’d immediately donate a large sum to whatever charity would ensure I remain clothed at all times. It would be less “I’ll pay you to walk naked” and more “Dear God, here’s a million dollars, please put your shirt back on.”

The Barefoot Factor

But let’s talk about the real horror of this scenario that nobody seems to be addressing: you’d be barefoot. Four blocks. Downtown. Do you know what’s on downtown sidewalks? I don’t know specifically, but I know I don’t want it touching my bare feet. We’re talking about gum, questionable liquids, broken glass, and things that even shoes don’t want to encounter.

The nudity is embarrassing, sure, but tetanus is forever. Or at least until you get a shot, which would be another fun conversation. “So how did you step on that rusty nail?” “Well, doc, there was this eccentric millionaire…”

And let’s consider the logistics. Four blocks isn’t a quick jaunt. That’s probably a solid five to seven minutes of walking, depending on your pace. Though I imagine when you’re naked, you’re either walking very quickly to get it over with or very slowly because you’re paralyzed with regret. Either way, that’s a long time to be making direct contact with urban pavement.

The Hannah Waddingham Exception

Okay, I’ll admit there’s one scenario where I might consider it. If Hannah Waddingham was following me down the street with a bell shouting “SHAME!” over and over again, Game of Thrones style, I might do it. Not because it would make it better, but because at least then it would be performance art. There’s a big difference between “random naked guy on Main Street” and “elaborate Game of Thrones recreation for charity.”

Plus, if you’re going to be humiliated, you might as well lean into it with a cultural reference. It transforms the whole thing from “what is wrong with that person?” to “oh, I get it, it’s that thing from that show!” Still mortifying, but at least with a narrative structure.

The Online Immortality Clause

And then Stock throws in that delightful little kicker: “What if you knew your stroll would be posted online?”

Oh, well, that changes everything! Said no one ever.

If I wasn’t going to do it for the live audience of whoever happens to be downtown that day, I’m certainly not doing it for the eternal audience of the internet. The internet doesn’t forget. The internet doesn’t forgive. The internet takes that video, turns you into a meme, and suddenly you’re “Naked Charity Guy” forever.

Your grandkids would find it. Your coworkers would find it. That person you had a crush on in high school would find it and think, “Wow, I really dodged a bullet there.” Every job interview would start with, “So, I Googled you and…” Every first date would end before the appetizers arrived.

The mathematics here are simple: temporary embarrassment in front of strangers < eternal embarrassment in front of everyone with WiFi.

The Moral Mathematics

Let’s talk about the supposed moral high ground of this scenario. Yes, charity is good. Helping others is admirable. But there’s something fundamentally wrong with the equation of “your humiliation = someone else’s benefit.”

It’s like a twisted version of effective altruism where instead of calculating the most good per dollar, we’re calculating the most good per unit of personal dignity sacrificed. How many hospital wings equal one naked stroll? How many scholarship funds equal the death of your professional reputation?

And what kind of charity would even want this money? “Great news, everyone! We’ve fully funded the new community center! The money came from Steve walking naked down Broadway. We’ve actually named it the Steve’s Naked Walk Memorial Center. The ribbon-cutting is next Tuesday, and yes, Steve will be clothed for it.”

The Slippery Slope of Charitable Humiliation

If we normalize this kind of charitable giving, where does it end? Today it’s walking naked down the street. Tomorrow it’s “I’ll donate a million dollars if you’ll let me broadcast your colonoscopy.” Next week it’s “I’ll fund the new library if you’ll karaoke ‘My Heart Will Go On’ at your ex’s wedding.”

We’d end up with a whole economy of embarrassment, where the rich entertain themselves by watching the rest of us debase ourselves for good causes. It would be like Black Mirror met The Hunger Games met a particularly aggressive NPR pledge drive.

The Gender and Body Type Elephant in the Room

Without getting too deep into it, we all know this scenario plays out differently for different people. Some folks have the confidence and the conventional attractiveness to pull this off as a funny story they tell at parties. “Remember that time I raised fifty grand for charity by streaking downtown? Classic me!”

Others of us would need therapy just from considering it. And extensive therapy after actually doing it. The charity better be mental health-focused because that’s where a significant portion of the donation would need to go just to undo the psychological damage.

The Practical Concerns Nobody Mentions

Can we talk logistics for a moment? The question says you step out of a car and walk four blocks before getting back in. But where does the car go? Does it creep along beside you like the world’s worst escort vehicle? Does it circle the block? Is there a designated driver who has to witness this whole thing and then make eye contact with you afterward?

And what about weather? The question doesn’t specify. Am I doing this in January? Because frostbite in unfortunate places isn’t just embarrassing, it’s medically concerning. Or is it August, when the pavement could literally cook an egg and I’m the egg?

What about law enforcement? Even if the millionaire has somehow arranged for this to be legal, you know someone’s calling the cops. And then you have to explain to an officer that no, you’re not having a mental health crisis, you’re just really committed to charity.

The “But Think of the Good You Could Do” Argument

I know someone out there is thinking, “But Aaron, imagine if it was a million dollars for cancer research. Wouldn’t a few minutes of embarrassment be worth potentially saving lives?”

To which I say: If this millionaire cares so much about cancer research, they could just donate the million dollars. The naked walk isn’t a necessary component of the donation. It’s not like the cancer cells are going, “We would have been cured, but the donation didn’t involve enough public humiliation.”

The only purpose of the nudity clause is the millionaire’s entertainment. And if someone needs to see me naked to be motivated to donate to charity, then we have bigger problems as a society than underfunded nonprofits.

My Final Answer

So no, there’s no amount that would get me to do this. My dignity might be negotiable in some circumstances (I have a blog where I regularly overshare, after all), but not for this particular trade.

The eccentric millionaire can keep their money, or better yet, donate it without the weird stipulations. And I’ll keep my clothes on, continuing to do my small part for charity in ways that don’t involve traumatizing downtown pedestrians or becoming an internet sensation for all the wrong reasons.

Besides, I genuinely believe I’m performing a greater public service by remaining clothed. Sometimes the most charitable thing you can do is know your limitations. And my limitation is that no one needs to see that. No one.

Your Turn

Alright, I’ve thoroughly explained why I’ll be keeping my clothes on for the foreseeable future. But what about you? Is there an amount that would get you to take this walk of shame for charity? Would it matter what cause the money went to? Would the online posting be a deal-breaker, or would you see it as extra publicity for the cause?

Have you ever done something embarrassing for charity? (And I mean intentionally embarrassing, not like that time you tripped at the charity 5K.) Where do you draw the line between helping others and maintaining your dignity?

And for those brave souls who would do it—what’s your number? What donation would get you out of that car and onto that sidewalk? And more importantly, what charity deserves to benefit from your sacrifice?

Drop your thoughts in the comments below. Let’s discuss how we’d handle this hypothetical humiliation, from the safety of our fully clothed positions behind our keyboards.

Until next week, when Gregory Stock will undoubtedly find yet another way to make us uncomfortable, this is Aaron, still here in The Confusing Middle, still fully clothed, still believing that some things are worth more than money—and my dignity, whatever’s left of it, is apparently one of them.

Feature Photo by Nout Gons