Our Most Embarrassing Experiences at Disney World

Let’s face it, we all make mistakes at Walt Disney World. Whether it’s your first or fifteenth trip, you’re bound to have a few big blunders. We’ve all been there. This type of thing is so common that you shouldn’t turn red in the face, especially since the complicated and convoluted process WDW uses for literally everything makes mistakes and confusion inevitable.

Here is just a short list of embarrassing experiences at Walt Disney World, some of which may or may not have happened to us relatively recently:

  • Misreading Disney’s cutesy signage and going into the wrong restroom
  • Forgetting which finger you used at the tapstiles and backing up the line behind you at Early Entry
  • Wearing Frogg Toggs and a bucket hat around to keep cool in the Florida heat
  • Awkwardly making (very forced) small talk with a princess at a character meal
  • Doing that dance where you and an oncoming stranger both try to avoid one another by moving in the same direction…repeatedly
  • Briefly getting stuck on Seven Dwarfs Mine Train (stupid camera bag), Space Mountain, etc.
  • Accidentally “stealing” someone’s lounge chair due to similar towel and sandals (probably happens all the time with ECVs and strollers, too)
  • Assorted Genie+ goof ups
  • Crying during Country Bear Jamboree
  • Crying when meeting famous celebrity (Big Al)
  • Tripping on Main Street trolley tracks or random curbs
  • Fistfight with bird trying to steal Flame Tree BBQ feast
  • Pooped on by bird

These are all pretty common experiences to the point that they barely bear mentioning. I mean, who among us hasn’t shed a single tear at the grace and majesty of Country Bear Jamboree (there’s a reason they made it a UNESCO World Heritage Site!) or perhaps gotten a little too excited after stumbling upon a rare character to the point that other guests gave a bit of side eye. C’mon, we’re all Walt Disney World fans here, we’re just built differently!

That’s not what this list is about, though. This is not a list of ‘cautionary tales’ that will help you avoid making similar mistakes and having similar embarrassing experiences. (Well, it sorta is–some of those bullet points above really do happen frequently.) Rather, this is us pulling back the curtain and sharing some of the dumb stuff we’ve done in the 15+ years we’ve been doing Walt Disney World together.

I would hazard a guess that almost all of these will be unique to us, and not a mistake that you could make. So this post really serves no practical purpose, save for giving you a laugh at our expense. And isn’t that truly the greatest gift of all?!

One of the (many) things we hate about social media is how everything is picture-perfect, romanticized and totally unrealistic. Influencers present only what they want you to see–the good of their lives, and seldom the bad. There are a ton of reasons why this is unhealthy, and creates aspirations for a reality that does not exist.

You’ll find none of that here. Although Sarah’s hair somehow and against all odds can beat the Florida heat and humidity, we’re real people, warts and all. We’ve make mistakes, have had our share of embarrassing experiences, and–as my grandma puts it–don’t always think with our heads.

(In actuality, the “we” on this list is mostly me. I’ve been told I have “middle age absent-minded professor energy,” which I can only assume is high praise since it means that I am literate and competent at teaching.)

Ghostface Killah – The whole idea for this post was prompted by my many mishaps this year and, I’m gonna be honest, these are 100% Sarah’s fault. Not to feed into a stereotype of anything, but she is basically the guardrails preventing me from doing or saying dumb things and making bad choices.

In this particular case, Sarah bought me new industrial strength sunscreen that is more like a thick paste or goo than it is a lotion. This “had to be done” because I kept forgetting to reapply regular strength sunscreen and was coming home sunburnt.

Anyway, like a total doofus, I apply this sunscreen like a normal lotion and go on with my business around Magic Kingdom. Fast-forward several hours later. I’m coming out of the restrooms near Space Mountain in Tomorrowland and catch a glimpse of myself, looking like I’ve just seen a ghost. I had talked to several people during the intervening hours and been all over the parks. I was mortified, which at least gave my face a nice red glow, I guess.

The worst part? This has happened more than once. Never nearly as extreme as that (it was really bad!), but there are actually several photos on the blog where I look paler than normal. This new sunscreen is the culprit.

Threat Level Midnight – Long before this blog was even a mere flicker in my eye, I was active on Flickr (remember that?) trying to teach myself photography and improve my skills. We made a lot of great friends then, and ended up taking multiple long weekend photo-centric trips.

The first of those was weird, but not in a meeting-strangers-from-the-internet way (to the contrary, pretty much everyone we’ve met in real life from the Disney fandom has been awesome). Rather, it was due to two separate encounters with security.

The first of these was in Magic Kingdom, when a security guard questioned what we were doing with our photos, trying to tie tripods to terrorism. (I’m not even kidding.) It made zero sense whatsoever, as we were photographing the old Swan Boat dock and Plaza Rose Garden. I cannot believe terrorists have a keen interest in those things, although now that I think about it, maybe that’s why they were removed.

A night or two later, we were all questioned in front of Spaceship Earth while taking photos of the monorails. This one at least made more sense given that the monorails are infrastructure, and honestly spooked us a bit. It still didn’t completely check out, though. If we wanted to ‘document’ the monorails, why wait until we were the only guests left in the park? I’m guessing most bad actors are more discreet, and not drawing attention to themselves by taking long exposure photos in the exact same spot for minutes on end.

In fairness, this was “only” 7.5 years after 9/11 and tripods were pretty rare in the parks. But I don’t recall having any major issues in the years immediately before or after that, so it was embarrassing and unsettling to have two run-ins on the same trip. (Maybe security was heightened and on edge for some reason?)

Room Rave – Speaking of security, earlier this year I was returning to my room at the Grand Floridian after a long night of Extended Evening Hours followed by the exhilarating activity of photographing Easter eggs in the lobby. It was sometime after 1 am, and I’m just ready to crash–barely able to keep my eyes open.

I round the hallway corner to see a half-dozen or more Cast Members knocking on my door. I was instantly awake, my heart racing. I didn’t have time to fully process the possibilities or game out what was going on, but my immediate thought was that someone planted something in my bag. (That makes zero sense in hindsight, but I had just watched American Made.)

I feebly said something along the lines of, “uh…that’s my room.” This somehow immediately de-escalated the situation, with a Cast Member saying something like, “oh that makes sense.” Apparently they had received a noise complaint, and had just gotten security to enter because no one was responding (since no one was in there).

The kicker, though, was that I had only entered my room for about 5 minutes to drop off my luggage and had immediately gone to the parks. The noise was coming from the welcome melody on the television, which I hadn’t touched because it didn’t occur to me. I was incredibly apologetic for whatever reason, and based on the response from the Cast Members, this is not an uncommon occurrence.

Despite being utterly exhausted 5 minutes earlier, I couldn’t calm down and get to sleep for another couple of hours. Nevertheless, I was awoken bright and early the next morning by my neighbors talking in what sounded like normal indoor voices. Perhaps it was passive aggressive revenge, but I think the true villain here was the paper-thin walls of the Grand Floridian.

Tequila SunsetDuring our Disneymoon almost 15 years ago, we set aside one day to drink around World Showcase at EPCOT, ending with the then-new La Cava Del Tequila. This wasn’t our first rodeo, we had drank around the World a few times before this, and had a pretty good idea of how to do so responsibly by pacing ourselves with snacking, attractions, hydration, and breaks. Or so we thought.

As it turns out, drinking around World Showcase as a college student is a lot different than drinking around World Showcase as sleep-deprived newly-weds who hadn’t had much alcohol for months while wedding planning and trying to get into shape. Funny how that works. Thankfully, we knew better than to get sloppy at Walt Disney World.

What the alcohol did do was diminish our judgment and reduce inhibitions, and we made fast friends with another couple at the bar. They were high rollers and tequila connoisseurs (at least, that was my impression at the time as someone who almost exclusively drank Busch Light), and ordered us a few shots and drinks. When it came time to settle up, they were happy to pay for the celebratory drinks.

However, I insisted that we pay for our own drinks. There was a back and forth, but I was pretty emphatic that we were going to pay for ourselves. To this day, I couldn’t tell you why. Then I was handed the bill, and my heart sank and my face turned bright red. But stubborn as I was, we paid even over their objections. Again, zero clue why. We had out after out that we didn’t take. Suffice to say, we’ve never drank around World Showcase at EPCOT again.

Restroom Regrets – Ah, who among us hasn’t had a bad (or good) feast at Chef Mickey’s that, uh, did some damage later. No? Me neither. So it’s a good thing that’s not actually what this is about.

My camera strap is a sling, which means the lens dangles at my waist (see above). Usually, I have one hand on the camera at all times because I’ve had the strap fail in the past and lost a lens this way. That’s not really doable in the restroom from a logistical perspective, so it bounces around. On one occasion, my telephoto lens was attached and the camera hit my hip in just the right (or rather, wrong) way, causing the camera to loudly fire a series of shutter bursts.

This was like a decade ago, but I still vividly remember the weight of every eye in that restroom turning towards me, and stuttering to get words to come out of my mouth in some stupid attempt to explain. Like a bad out of body experience. Thankfully, no one got confrontational–I think it was pretty obvious the lens was photographing the ground given the orientation of the camera–but suffice to say, I always check to make sure the camera is turned off and the lens cap is on before entering restrooms now.

Solo Roundup – I’ve made a lot of solo visits to Walt Disney World this year, as Sarah had been trying to mitigate risk while pregnant. I’ve done some meals with others, but oddly enough, none of my thirtysomething friends wanted to eat at Toy Story Roundup Rodeo BBQ. So, I opted to eat there alone.

I want to preface this by saying that I actually enjoy eating by myself sometimes. This was not one of those times. I was seated at the very front of the restaurant, at a table every party would pass on their way to be seated, and right next to a little prep station for servers. I was already slightly uncomfortable to be a solo adult male in a kids restaurant, and being on fully display exacerbated it.

What really put things over the top was that the kitchen couldn’t prepare smaller size portions, so I got a whole ton of food brought out to me. And of course, I’m photographing all of this food. (My own “fault,” so to speak, but did me no favors in making myself less conspicuous.) Even if Sarah were with me, this would’ve been way too much food–I’ll bet we could’ve only finished half of it.

By myself, I was only able to eat a little less than half of it, and that was only after going way too hard to minimize the waste. When my server arrived, I proactively commented on this and apologized for the food waste. To her credit, she completely unfazed and told me not to worry about it–that she had seen far, far worse and that Walt Disney World recycles all of the food (not to future patrons–this isn’t Chuck E. Cheese), so it didn’t matter.

Although I’m familiar with Walt Disney World’s commitment to reducing and diverting food waste, I’d still rather not be in that position in the first place. I haven’t done any family style meals by myself since Toy Story Roundup Rodeo BBQ.

Masks Off – This one barely registers now, but the world was a different place in Summer 2020. Having been largely confined to our home for the prior few months, we did a number of hotel stays as soon as Walt Disney World began its phased reopening. Rates were low, and availability was abundant via DVC.

One of those mornings, I raced out of the room to photograph the sunrise on Crescent Lake. As I was making my way through the lobby of Beach Club, I saw a Cast Member in a face mask. The next few seconds happened in slow motion, as I realized I wasn’t wearing a mask at the same time that they said something. I apologized profusely and began (over)explaining what happened, worried that security was going to get called or something, I guess?

Even at the time, it was a bigger deal in my head than anything. The Cast Member was understanding, security was not called, and I simply ran up to the room and grabbed my mask. It might seem like nothing in retrospect, but again, very different circumstances in July 2020. I was absolutely mortified.

Fake Fame – On occasion, readers come up to us in the parks and say hello or whatever. We generally like this. It’s nice to chat with people and get feedback about the highs and lows of their trip, how our itineraries and other planning advice worked (or didn’t), etc.

Sometimes, people are excited to meet us and, uh, audibly express that. I can somewhat understand this; I’d be excited to meet Sarah, too! This is not awkward in and of itself, but it can be when other guests in the general vicinity then follow up by asking, “are you famous?” That’s the kind of question that answers itself. Do I look famous in my bucket hat, athletic shirt, and Crocs?

Disney blogging may seem like a cool thing to like 3.5% of you, but I can assure you that it is a cool thing to 0.0% of the non-Disney-blog-consuming public. Explaining to a stranger why someone is excited to meet me, a Disney blogger, as they give me a dead-eyed stare is excruciating for all involved. Next time I’m just saying I’m an astronaut.

While we’re on the topic, please say hello if you see us in the park! We really enjoy chatting. But also, please don’t get too excited about it. Trust me, if you are overly enthusiastic, you might be setting up disappointment for yourself…and others around you. I’m about the furthest thing from a celebrity as you can conceivably imagine. Sarah is cool, though.

Contemporary Shoes – I have this problem, you might even call it a condition, where I don’t fully think through decisions to their logical endpoint. I take decisive action. Sometimes, that’s a good thing. In this scenario, it very much was not.

Sarah and I had just checked into the Contemporary, and she had to go pick up a package or something. It had been raining, and my shoes were a bit wet, so I decided to rapidly accelerate the dehumidifying process: I stuck a blow dryer inside one of them. Now, my feet always smell something awful when we’re at Walt Disney World. I guess this alone is low-level embarrassing–but unlike a lot of DVC members in the Imagination Lounge, I don’t take my shoes off in the parks, so it doesn’t matter.

What’s high-level embarrassing is how badly our room…and the hallway…smelled after only a few minutes of the rapidly accelerated dehumidification process. It was like a proprietary blend of burnt funguses. Sarah had a few choice words for me when she returned (thankfully, we had been married for several years at this point), wondering how I managed to stink up the room so efficiently in the few minutes that she was gone.

I can’t watch the scene in Community where Troy enters the fire-filled room without picturing Sarah’s reaction. Same goes for the scene in The Office where Kevin gets his shoes incinerated by the hotel staff due to them being a safety issue, which makes me think back to finding an out of the way trash can at the Contemporary to ditch my kicks. On the plus side, both scenes are especially funny as reminders of this ‘fun’ memory.

Fulton’s Feast – There were probably a number of times I was embarrassed during my childhood trips to Walt Disney World, especially the visits that bled into my teenage years, that awkward time when everything your parents do agitates you. I know my mom has her own list of things my dad–a military man without a filter–said. But I don’t actually remember any of that; I remember hearing the stories over the years.

What I do vividly remember is eating at Fulton’s Crab House aboard the elegant Empress Lilly (now known as Paddlefish) in the mid to late 1990s. This was quite a extravagant meal for us country folk, and was easily the nicest meal I had ever eaten in my life up until that point. We were seated upstairs, in a bit of a quiet corner, and my parents told me to order whatever I wanted. I was so excited. I felt like royalty.

I’m not sure I had ever had crab (spelled with a “c” instead of a “k”) before in my life, so I ordered that. It was delicious. It was tender, buttery, succulent, buttery, flavorful, and did I mention buttery? Unfortunately, the reason this meal is probably so memorable for me is because it’s one of the few meals in my life that caused me to get…let’s just say “sick.”

I swore off seafood for several years after that (thankfully, it didn’t stick) and at the time, it was not just embarrassing–but disappointing that this special experience turned negative. But there’s a decent chance I wouldn’t remember it at all but for that. Most importantly, I remember my parents being gracious and caring when they could’ve been angry or annoyed that their boneheaded son dousing his seafood in like a pound of butter. I guess that sort of speaks to the silver lining in almost all of this–every indelible experience shapes us a little, even the embarrassing and bad ones.

Planning a Walt Disney World trip? Learn about hotels on our Walt Disney World Hotels Reviews page. For where to eat, read our Walt Disney World Restaurant Reviews. To save money on tickets or determine which type to buy, read our Tips for Saving Money on Walt Disney World Tickets post. Our What to Pack for Disney Trips post takes a unique look at clever items to take. For what to do and when to do it, our Walt Disney World Ride Guides will help. For comprehensive advice, the best place to start is our Walt Disney World Trip Planning Guide for everything you need to know!


Anyone else care to share you or your family’s embarrassing experiences at Walt Disney World? Do your most mortifying moments in the parks beat ours? Have you had any similar experiences to the ones on this list? Thoughts on our/my dumb mistakes at Walt Disney World? Any questions we can help you answer? Hearing your feedback—even when you disagree with us—is both interesting to us and helpful to other readers, so please share your thoughts below in the comments!

29 Responses to “Our Most Embarrassing Experiences at Disney World”
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