Welcome back to another Question of the Week here at The Confusing Middle! For those brave souls who continue to join me on this weekly journey through psychological discomfort, I’m once again cracking open Gregory Stock’s The Book of Questions to share whatever fresh hell he’s prepared for us. We’ve reached week 470, and I’m starting to think Gregory might need a hobby that doesn’t involve cataloging every possible way humans can experience social agony.

This week’s question: Which would be worse: being naked in public, getting spit on by strangers, arrested for shoplifting, throwing up on someone at dinner, or begging on the street?

Well, Gregory, I see we’re following up last week’s nudity-for-charity scenario with… more nudity. Plus a delightful buffet of other mortifying options. Are you okay? Do you need to talk to someone? Because this feels like you’re working through something, and we’re all just along for the deeply uncomfortable ride.

Gregory Stock’s Greatest Hits

Before we dive into this week’s smorgasbord of shame, can we just acknowledge that Gregory has a thing about public nudity? Last week it was “would you walk naked for charity?” This week it’s back on the menu of horrors. I’m starting to think Gregory had a traumatic experience at a clothing-optional beach and he’s been processing it through philosophical questions ever since.

But at least he’s given us options this time. It’s like a multiple-choice test where every answer makes you want to change your name and move to another country. Thanks for the variety, I guess?

The Worst of the Worst

Let me cut right to the chase: being naked in public is absolutely the worst option on this list. And before you think I’m being inconsistent or wishy-washy, let me remind you that last week I said no amount of charitable donations would get me to take that four-block stroll in my birthday suit. I stand by that position, fully clothed, thank you very much.

The thing about public nudity is that it combines so many different flavors of mortification. There’s the immediate physical discomfort (where do you put your hands?), the social humiliation (everyone’s looking and no one’s making eye contact), the legal concerns (pretty sure this is illegal in most places), and the eternal documentation (everyone has a phone with a camera).

Plus, unlike some of these other scenarios, nudity doesn’t happen quickly. You can throw up in seconds. Getting spit on is momentary. But being naked? That’s an ongoing state of being until you find clothes. Every second stretches into eternity when you’re standing there in nothing but the confidence you definitely don’t have.

The “Least Worst” Option

Now, you might find this surprising given what I’m about to tell you, but throwing up on someone at dinner would be my pick for least awful. And this is coming from someone who is genuinely, legitimately almost phobic about vomiting. The thought of it makes me anxious. The sound of it makes me leave the room. I haven’t thrown up since 2014, and I intend to keep that streak going indefinitely.

But here’s the thing—and I say this as someone who has been vomited on before (thanks, kid who ate too much pizza at that sleepover back in 6th grade)—at least vomiting is involuntary. Nobody thinks you chose to projectile express your dinner onto their lap. It’s mortifying, sure, but it comes with a built-in excuse: you were sick.

People might be disgusted, they might be angry about their ruined outfit, but they’re also likely to show some concern. “Are you okay? Do you need water? Should we call someone?” Try getting that sympathy when you’re arrested for shoplifting or standing naked in a Walmart.

The Spitting Situation

Getting spit on by strangers is awful, don’t get me wrong. It’s degrading, it’s disgusting, and it’s assault in most jurisdictions. But notice the question says “strangers,” plural. What scenario leads to multiple strangers spitting on you? Are you in stocks in medieval times? Did you just announce your support for pineapple on pizza at an Italian cultural festival?

The logistics alone make this seem less likely to happen organically. You’d almost have to orchestrate it, which means on some level you’d be prepared for it. Unlike, say, accidentally walking through the wrong door at the gym and ending up in the pool area during senior water aerobics while fully nude. That’s the kind of thing that just happens when the universe decides you need humbling.

But the real issue with being spit on is the immediate need for decontamination. You’d want to shower in hand sanitizer. You’d want to burn your clothes. You’d want to move to a different city where no one knows you as “that person who got spit on by an angry mob.”

The Shoplifting Scenario

Being arrested for shoplifting carries a special kind of shame because everyone assumes guilt. Even if it’s a misunderstanding, even if you can prove your innocence, there’s always that moment where everyone in the store is looking at you like you’re a criminal.

I still remember being about ten years old, walking out of a store with my mom, and having the alarm go off. Even though we hadn’t done anything wrong—turns out the cashier forgot to remove a security tag—that feeling of everyone staring, everyone judging, everyone assuming the worst… it stays with you.

Now imagine that, but with actual handcuffs. And a real arrest. And having to explain it on job applications for the rest of your life. “Have you ever been arrested?” “Well, yes, but it was a misunderstanding involving a candy bar and an overzealous security guard…”

The legal implications make this one particularly brutal. The other scenarios might haunt your dreams, but this one haunts your background check.

The Begging Question

This one hits differently because it touches on real struggles that real people face every day. I would never wish that situation on anyone, and I can’t judge someone for doing what they need to do to survive. You never know what someone is going through, what led them to that point, what they’re dealing with behind the brave face they’re putting on.

That said, the question is asking about the personal experience of it, the emotional impact of having to ask strangers for help in such a public, vulnerable way. And that would be devastating. The rejection, the judgment, the people who look through you like you don’t exist—it would chip away at your soul in a way the other scenarios wouldn’t.

I’ll be honest about something that might not make me look great: I rarely give money to people panhandling. For one thing, I never have cash anymore—I’m basically living in a cashless society at this point. But also, I’m admittedly cynical about it, especially when I see people at intersections with signs saying panhandling is illegal there while also providing information about local resources.

There’s always that urban legend about panhandlers being dropped off for “shifts” like it’s a job. And while I know that’s probably more myth than reality in most cases, it’s made me hesitant. If that makes me unsympathetic, I apologize. I know there are many resources available in my community that go underutilized, and if I had the means, I’d love to do more to support those organizations that help the unhoused.

But the personal humiliation of having to beg, of having to put yourself at the mercy of strangers’ kindness (or lack thereof), would be profound. It’s a vulnerability that goes beyond embarrassment into something deeper and more painful.

The Hierarchy of Humiliation

If we’re ranking these from least to most awful (for me personally):

5. Throwing up on someone at dinner – Horrible, but at least you have the “I was sick” excuse. Plus, it’s over quickly, even if the memory lingers forever.

4. Getting spit on by strangers – Disgusting and degrading, but you’re clearly the victim here. No one’s going to blame you for being spit on (unless you really, really deserved it, which raises other questions).

3. Begging on the street – The emotional and psychological toll would be immense, but at least there’s no legal record or viral video potential.

2. Being arrested for shoplifting – The legal ramifications make this a nightmare that keeps on giving. Every job application, every background check, every time someone Googles you.

1. Being naked in public – Just no. Absolutely not. Never happening. I said it last week, I’m saying it this week, and I’ll keep saying it until Gregory Stock finds a new obsession.

The Modern Twist

What makes all of these scenarios worse in 2025 is the documentation factor. Every one of these moments would likely end up on someone’s TikTok, Instagram story, or Twitter feed. You wouldn’t just be experiencing the mortification once—you’d get to relive it every time someone shared, commented, or turned you into a meme.

Imagine being the “dinner vomit guy” or the “naked person at Target.” The internet doesn’t forget. Your grandchildren would see it. Your future employers would find it. That person you had a crush on in high school would share it with the caption “dodged a bullet with this one lol.”

Your Turn

So there you have it—my deeply personal ranking of Gregory Stock’s menu of mortification. Being naked in public remains my ultimate nightmare, while throwing up on someone at dinner is somehow the option I find least catastrophic (though still absolutely catastrophic).

But what about you? Which of these scenarios would be your personal worst nightmare? Is there one that doesn’t seem as bad as the others? Have you actually experienced any of these situations and lived to tell the tale?

And here’s a follow-up question: does the context matter? Would you rather be naked at a beach (where at least some people are barely dressed) or in a courthouse? Would you rather throw up on a stranger or your boss? Would being arrested for shoplifting a luxury item be worse than being caught with a single grape at the grocery store?

Drop your thoughts in the comments below. Let’s commiserate over these hypothetical humiliations from the safety of our fully clothed, law-abiding, non-vomiting positions behind our keyboards.

Until next week, when Gregory Stock will undoubtedly find new and creative ways to make us squirm (possibly involving more nudity if the pattern continues), this is Aaron, still here in The Confusing Middle, still clothed, still keeping my dinner down, and still grateful that these are hypothetical questions and not required experiences.

Though at this rate, I’m half expecting next week’s question to be “Would you rather be naked while being spit on, or throw up while being arrested?” Gregory, seriously, are you okay?