Welcome back to another Question of the Week here at The Confusing Middle! After last week’s easy slam-dunk about accepting $150,000 a year to never work again (spoiler: yes, obviously yes), we’re pivoting to something considerably less hypothetical and significantly more uncomfortable. Gregory Stock is apparently done letting us fantasize about financial freedom and is now coming for our emotional vulnerability.

This week’s question: When did you last cry in front of another person? To yourself?

Well, This Got Real Quick

You know how sometimes a question seems simple on the surface, like Stock is just making conversation at a dinner party, and then you actually start thinking about it and realize you’re about to get emotionally excavated? This is one of those questions.

I could lie. I could make something up that sounds profound and dignified. “Oh, I cried at my grandmother’s funeral a few years ago” or “I shed a single, cinematic tear while watching Up for the first time.” You know, the kind of crying that comes with a soundtrack and soft lighting, where you dab at your eyes with a handkerchief like you’re in a black-and-white film about the human condition.

But that’s not what happened. What actually happened is significantly less poetic and way more recent than I’d like to admit.

The Ugly Cry at Work (A Horror Story in Three Acts)

Let me set the scene: It’s mid-December 2025, and I’ve just started a new position at work. Same organization, different role. For those who don’t follow my professional saga (and why would you?), I work in early childhood education coordinated enrollment. I took on a new position that, under normal circumstances, would have a learning curve. A manageable learning curve. The kind you tackle with some training, a few stumbles, and eventually competence.

These were not normal circumstances.

What I actually inherited was the professional equivalent of someone handing you a dumpster fire and saying “good luck!” and then immediately going on vacation. Years of mismanagement, systems held together with digital duct tape and prayer, processes that made sense to exactly no one, and documentation that might as well have been written in ancient Sumerian for all the help it provided.

About a week into this new position—a week!—I hit my breaking point. And when I say “breaking point,” I don’t mean I got a little frustrated or needed to vent. I mean I completely fell apart. In front of people. In front of my supervisor. In front of the person above my supervisor.

I tried to hold it in. I really did. Because here’s the thing about crying in public: it’s not dignified. It’s not pretty. I get snotty. My breathing becomes this weird hiccup-gasp hybrid that sounds like a broken accordion. My face does things that faces shouldn’t do. It’s the opposite of that single cinematic tear I mentioned earlier. This was the full ugly cry, the kind where you’re simultaneously trying to explain what’s wrong while your body is actively betraying you.

And the worst part? I hate crying in front of people. Not because I think crying is wrong—cry if you need to cry! Express your feelings! I’m very pro-emotion in theory. But in practice? In practice, crying in front of others feels like showing up to a meeting with my pants on backward. It’s embarrassing. It’s vulnerable in a way that makes me want to crawl into a hole and live there forever with the other emotionally compromised mole people.

The Sequel Nobody Asked For

You’d think that would be it. You’d think I’d learned my lesson, developed better coping mechanisms, maybe invested in some stress management techniques or at least a punching bag.

About a month later, I was working from home—because apparently the universe has a sense of irony and made sure I was physically isolated when I needed support. It had been another brutal week. The kind of week where every problem has three more problems hiding inside it like Russian nesting dolls of professional despair.

I was sitting at my desk, staring at my computer screen, and I just… lost it. Completely. The dam broke and I spent several minutes engaged in what can only be described as a full-system emotional purge.

The question asks about crying “to yourself,” and technically I wasn’t alone. Krypto was there. My dog, my loyal companion, my best friend. Surely he would provide comfort in my moment of need, right?

Wrong.

He just laid there. Staring at me. With those big dog eyes that seemed to say, “I don’t know what’s happening, but I’m concerned about my dinner schedule.” He didn’t come over. He didn’t put his head in my lap. He didn’t do any of those heartwarming things that dogs do in commercials where they sense their human’s distress. He just… observed. Like a furry, judgmental therapist who specializes in saying absolutely nothing.

So that’s my answer. The last time I cried in front of another person? About six weeks ago, in what I’m choosing to call “The Incident We Don’t Discuss at Staff Meetings.” The last time I cried alone (sort of)? About a month ago, with my emotionally unavailable dog as witness.

If those two incidents hadn’t happened, I genuinely don’t know when I could tell you about a real cry. Not the misty-eyed response to a sad movie or a particularly moving song—I’ll get to that—but actual, emotion-driven, cathartic sobbing? It’s been rare enough that these two work-related breakdowns stand out like landmarks in my emotional landscape.

The Media Crier’s Paradox

Here’s what’s interesting, though: while I rarely cry about my actual life, I have become increasingly susceptible to crying at fictional scenarios. YouTube videos of soldiers coming home to surprise their families? Waterworks. That scene in The Lord of the Rings where King Aragorn tells the hobbits they bow to no one? Every. Single. Time. Songs I’ve heard approximately 3,500 times that hit just right on a particular day? Suddenly I’m emotional.

I’ve noticed this trend getting worse—or better, depending on your perspective—as I’ve gotten older. In my twenties, I was a stone. Impervious. Emotionally fortified. Now, in my forties, I can get choked up at a particularly well-crafted commercial for paper towels if it involves a parent-child moment or a dog doing something heroic.

But real, heaving sobs based on genuine personal emotion? That’s rare. Rarer? More rare? Whatever the grammatically correct version of “not happening often” is. Which makes those two work incidents stand out even more. My threshold for fictional sadness has apparently lowered while my threshold for personal stress has remained stubbornly high, until it suddenly isn’t, and then it’s spectacular demolition.

The Masculine Mystique of Moisture Control

I should probably address the elephant in the room: I’m a man, and we have… let’s call them “cultural expectations” around crying. Generations of messaging about what it means to be a man. The stoic ideal. The strong, silent type. The “boys don’t cry” nonsense that we’ve been marinating in since someone decided that half the population should just suppress their feelings until they die of stress-related heart attacks at 55.

Ron Swanson, that beacon of masculine wisdom from Parks and Recreation, famously stated that crying is only acceptable at funerals and the Grand Canyon. And look, I love Ron Swanson. I consider him a personal hero. The man has real wisdom about breakfast foods, government inefficiency, and the importance of a good chair.

But on this one? He’s wrong.

I get it. I understand where the sentiment comes from. There’s something appealing about emotional restraint, about being the rock that others can depend on, about not falling apart when things get hard. And I’m not saying we should all be crying constantly about everything. That seems exhausting and probably dehydrating.

But the idea that men should only cry at funerals and natural wonders? That’s ridiculous. That’s the kind of thinking that leads to exactly what happened to me: holding it in, holding it in, holding it in, until you can’t anymore and then you’re ugly-crying in front of your supervisor over a spreadsheet about preschool enrollment.

There’s nothing weak about crying. There’s nothing unmanly about having emotions and expressing them. If anything, constantly suppressing your feelings until you have a breakdown seems like the less functional approach. And yet, that’s what I did. Because even though I intellectually reject the idea that crying is shameful, I’m still conditioned enough by society that my first instinct when the tears started was to try to stop them, to apologize, to be embarrassed.

The Public vs. Private Divide

Stock’s question cleverly separates crying in front of others from crying alone, and there’s wisdom in that distinction. Because they really are different experiences, aren’t they?

Crying alone is… well, it’s not exactly cathartic, but it’s at least honest. There’s no performance anxiety. No concern about what the other person is thinking. No need to simultaneously experience your emotions and manage someone else’s reaction to your emotions. When you cry alone, you can just be in it. You can let it happen without the meta-layer of embarrassment.

Crying in front of others, though? That’s a whole different thing. Suddenly you’re not just dealing with whatever made you cry; you’re also dealing with the social dynamics of having cried. You’re watching them watch you. You’re aware of how you look, how you sound, whether you need a tissue or twelve. You’re probably apologizing—why do we do that? “Sorry for having feelings in your general vicinity”—even though they’re probably just uncomfortable because they don’t know what to do.

And here’s the thing: in both of my recent crying incidents, the stress that triggered the tears was the same. The overwhelm was identical. But the experience of crying in front of my supervisors versus crying in my apartment? Completely different. One left me feeling embarrassed for days. The other left me feeling relieved, like I’d lanced a wound and let the poison out.

Maybe that’s why I’m more comfortable crying at movies than at life. When you cry at fiction, there’s a script. There’s a reason that makes sense. “Oh, he’s crying because the dog died in the movie.” That’s understandable. That’s relatable. But “Oh, he’s crying because the childcare database is a disaster and he doesn’t know how to fix it”? That’s harder to explain. That sounds silly when you say it out loud, even though the stress is incredibly real.

The Embarrassment Factor

Let’s talk about the embarrassment, because I think that’s a huge part of why many of us avoid crying in public. It’s not just about the cultural messaging around masculinity or strength or any of that. It’s about the sheer physical awkwardness of it.

When I cry—really cry—I’m not pretty. This isn’t a couple of tears rolling gracefully down my cheeks while I maintain perfect posture and speak in measured tones. This is snot. This is gasping. This is that weird thing where you try to talk but your breath keeps hitching so you sound like you’re trying to communicate in Morse code. This is my face turning red and blotchy. This is needing multiple tissues and still not having enough.

It’s vulnerable in a way that feels almost medical. Like I’m showing people something they shouldn’t have to see, something private and unpleasant, like watching someone throw up or have a panic attack. Even though intellectually I know that crying is a normal human response to stress, in the moment it feels like I’m malfunctioning in public.

And the apologies! I apologized to my supervisors. Multiple times. For crying. For being stressed. For not having it together. As if the appropriate response to overwhelming circumstances is to handle them with perfect grace and composure. As if breaking down under pressure is a personal failing rather than a completely reasonable human response.

What the Tears Actually Mean

Here’s what I’ve been thinking about since these incidents: maybe the crying isn’t the problem. Maybe the crying is just the symptom.

Both times I cried, it was because I was overwhelmed. Not sad, specifically. Not grief-stricken. Just completely, utterly overwhelmed by the gap between what I was expected to do and what I felt capable of doing. The crying was my body’s way of saying “Hey, this is too much. We need to stop and acknowledge that this is too much.”

And maybe that’s okay. Maybe that’s even healthy. Because the alternative is what? Pushing through until I burn out completely? Pretending everything is fine when it demonstrably isn’t? Maintaining a facade of competence while internally drowning?

The crying, as embarrassing as it was, at least forced the conversation. It made my supervisors aware that I was struggling. It created space for them to offer support, to adjust expectations, to acknowledge that yes, the situation I walked into was objectively difficult. Would I have preferred to have that conversation without the snot and gasping? Absolutely. But would I have had that conversation at all if I hadn’t broken down? Probably not.

So maybe crying in front of people isn’t the disaster I think it is. Maybe it’s just honest. Messily, awkwardly, snotily honest.

The Dog Theory of Emotional Support

I do want to come back to Krypto for a moment, because his complete lack of reaction to my crying says something interesting about expectations.

We have this idea—promoted by countless movies and heartwarming stories—that dogs are emotionally intuitive creatures who sense our distress and comfort us. And maybe some dogs are. Maybe there are dogs out there who immediately spring into action when their humans are upset, offering cuddles and concern and unconditional love.

Krypto is not one of those dogs.

Krypto’s approach to my emotional crisis was essentially “This seems like a you problem.” He observed. He remained present in the way that inanimate furniture remains present. He did not judge, but he also did not help. He was the Switzerland of emotional support animals.

And honestly? There’s something weirdly freeing about that. He didn’t make it better, but he also didn’t make it worse. He didn’t get uncomfortable or try to fix it or ask me to stop. He just let me be upset without commentary. Sometimes that’s all you need—someone (or some dog) who doesn’t try to talk you out of your feelings or make it stop. Someone who just lets it happen.

Though a comforting head on the lap would have been nice, buddy. Just saying.

Moving Forward (Still Occasionally Crying)

I’m now about two months into this position, and I’m happy to report that I haven’t cried at the office since that first week. Whether this is because I’ve developed better coping mechanisms, because the situation has improved, or because I only occasionally make an appearance at the office remains to be seen.

But I do think about those two crying incidents differently now. At the time, they felt like failures—evidence that I wasn’t tough enough, wasn’t professional enough, wasn’t handling things the way I should. Now, with a bit of distance, they just feel like moments. Human moments. Moments where the pressure got too high and something had to give, and what gave was my ability to keep my emotions locked down.

And you know what? I survived them. Both of them. The world didn’t end. My supervisors didn’t fire me for having feelings. My dog didn’t file for emancipation. Life continued, now with the added knowledge that yes, I am in fact capable of completely falling apart, and yes, I can recover from that.

So when did I last cry in front of another person? Six weeks ago. When did I last cry alone (with apathetic dog supervision)? A month ago. And will I cry again? Probably. Hopefully not in front of my supervisors again, but I’m not making any promises.

Because here’s the thing Stock’s question really gets at: we all cry. Some of us more than others, some of us more publicly than others, some of us at funerals and the Grand Canyon and some of us at childcare databases and YouTube videos of soldiers coming home. But we all do it, because we’re human, and being human means sometimes the feelings get too big to keep inside.

Your Turn

So now it’s your turn. When did you last cry in front of another person? When did you last cry alone? Are you a public crier or a private crier? Do you cry at movies but never at life, or are you someone who just lets the tears flow whenever they feel like flowing?

Have you had one of those mortifying work-crying incidents, or do you have better emotional regulation than I do? (It’s okay, you can admit it. I know I’m a mess.) Do you think there’s something to the distinction between crying in front of others versus crying alone, or is crying just crying regardless of the audience?

And for my fellow men out there: how do you navigate the cultural expectations around crying? Have you internalized the Ron Swanson approach, or have you rejected it? Do you find yourself more or less likely to cry as you’ve gotten older?

Drop your thoughts in the comments below. Share your crying stories, your theories about emotional expression, or just tell me whether your dog is more emotionally supportive than mine (low bar, honestly). Let’s normalize talking about crying so maybe it doesn’t feel so embarrassing when it happens.

Until next week, when Gregory Stock will hopefully ask us something lighter (though given his track record, I’m not optimistic), this is Aaron, still here in The Confusing Middle, still occasionally crying at work and YouTube videos, and genuinely curious about how the rest of you handle the waterworks.