Ah, event planning—the glamorous world of perfectly timed schedules, seamless logistics, and unforgettable moments...right? Well, not always! 😅
Behind every flawless event, it's not uncommon for wedding and event planners to have a few near-disasters and last-minute fixes that keep them awake at night.
Sometimes, it’s best to take a moment and laugh about the stories of real-life blunders from the brave event planners who lived to tell the tale. Here’s to a good laugh (...and maybe even the chance to feel a little better about your planning disasters)!
💌 Have a story you think should be included in this article? I’d love to hear it! Let me know what happened at your event and what you learned by sending me an email.
Table of Contents
When you picture weddings, you probably think of a meticulously planned day with everything in order. Well, these 11 stories of weddings gone wrong show that not everything always goes as expected (and that's okay - everyone lived to tell the tale)! I would like to thank the wedding professionals who were kind enough to share their best stories with me. Enjoy!
“A few years ago, I was shooting a beautiful wedding at a vineyard. The weather was perfect, the couple was radiant, and everything seemed to be going smoothly—until it came time for the big cake-cutting moment.
Now, the bride had been raving about this cake for weeks. It was a massive, multi-tiered creation, complete with intricate fondant designs and real flowers cascading down the sides. The cake was placed on a special table near the dance floor, positioned just right so I could get the perfect shots. But as the couple approached to take the iconic cake-cutting photo, disaster struck.
One of the groomsmen, who was trying to sneak in a candid selfie with the couple, accidentally backed into the cake table. In what felt like slow motion, the cake tipped over—no exaggeration—right into the couple’s arms! There was a collective gasp from the crowd, and I thought, ‘Well, there goes the perfect wedding shot!’
But, as luck would have it, the bride and groom burst into laughter, embracing the chaotic moment. Covered in cake, they decided to start a spontaneous "cake fight" with their bridal party. I kept shooting the whole time, and those pictures turned out to be some of their favorites from the day!
In the end, what could have been a disaster became one of the most memorable parts of the wedding. The couple said it made their day even more special because it was completely unexpected and fun. Well, at least the caterers managed to save a few slices from the top tier for them to enjoy! Sometimes, the unplanned moments are the best ones to capture.”
Submitter: Jeffrey Wang, Wedding Photography and Founder of Perfect Moment Photography and Video
“I photographed a wedding once where the DJ must have illegally downloaded the song that the bride walked down the aisle to and not listened to it all the way through.
The song begins and the bride begins her long walk to the head of the aisle. Right as she's getting to the head of the aisle, a booming radio DJ voice cuts into the song, "You are listening to a [insert radio channel] exclusive!"
Luckily, I was in the back, so no one saw my jaw drop. Everyone seemed to manage to act as if nothing was happening. The DJ's voice cut in AGAIN one more time when she was at the front and her dad was giving her away.
The DJ ended up giving me his card at reception asking me to refer him to future clients and I was dumbfounded that he seemed so unphased by the massive blunder. Awkward!”
Submitter: Jessica Zais, Photographer at Jessica Zais Photography
“One of my first wedding planning ventures was for a close friend who was having a great big Italian wedding. They had the most beautiful four-tier wedding cake, and on each tier, it was loaded with miniature fruits of all sorts. The cake maker set it all up and left. Everyone was in awe of this cake!
Just before the doors opened for the guests to come in, we were doing the final walk-through. Everything was perfect. We walked towards the guests when we heard a strange thud. I turned around to see the entire cake all over the carpeted ballroom. All that white cream icing mixed up everywhere on the dark green carpet and little fruits as far as the eye could see.
The staff and I all stood in horrified awe. Then, we all seemed to snap out of it simultaneously. We had minutes before the bridal party would arrive to greet guests in the ballroom. Staff grabbed brooms and started sweeping the fruit, which ground the white icing into the carpet more. Someone had the bright idea of vacuuming it up, which I am sure ruined the vacuum but seemed to work best. We took wet rags and tried to get as much buttercream out as possible, but the stains were noticeable. We all looked at each other - walked to the head table, and moved the entire table over the stains!
I was on my hands and knees with others, picking up fruit and working my way in. We had to pick up huge chunks of cake from the main pile. It was a disaster, and it was the main dessert. So, the chef put the cake that had not touched the floor into large pans. He put it back into individual bowls, covered it with fruit, and poured a drizzle on top. The bride and groom were sure confused, but it tasted great!
I have never had anything that bad happen again unless you count the bride who went into life-saving emergency surgery on her wedding day. But that one is too stressful to talk about, really.”
Submitter: Laura Kalcsa, Writer and Editor at West Coast Weddings Magazine
“During my work as an event planner, I experienced an outstanding mistake. In the very last few hours before the wedding ceremony of a prominent person, we realized that the detailed, beautiful, multiple-layered cake was accidentally taken to the wrong hotel.
Crisis set in as we realized the bakery could not make a replacement in such a short time. Reacting quickly, I telephoned several local bakeries in an attempt to find one that could bake a simple but proper cake. I reassured the couple that every problem would be solved soon enough.
Finally, after several nervously placed telephone calls to bakeries, I managed to make arrangements for a small, compact yet gorgeous cake within the hour. Fortunately, the couple was content, and no guests realized what happened.
This was a good lesson for me. Such a bad experience taught me how to organize a good Plan B and C whenever there is pressure.”
Submitter: Sumit Raghav, Event and Exhibition Planner, NS Events and Exhibitions Fzc.
“I was hired as a live wedding painter at a beautiful outdoor wedding outside Maui. Everything was perfect until just after the vows when suddenly, a tropical rain shower appeared right in the middle of my live painting session!
I had to quickly move my easel and canvas to shelter, racing against the downpour to keep everything dry. I felt pressured to finish on time because I still needed to start sketching the guests. However, since I work with oil on canvas, the rain didn't affect the painting too much.
Once we were all under cover and the initial panic subsided, I continued the painting from the reception area. The change in setting brought a new kind of energy to the artwork—being closer to the guests added warmth and spontaneity, which I tried to capture on the canvas.
The unexpected change turned out to be a blessing in disguise—guests gathered around, curious about the painting process, and I even ended up drawing caricature portraits for them throughout the evening.
Although the chaos was mostly in my head, it became a moment that brought everyone together. The rain was refreshing, especially after the couple's emotional love story. It’s a story that the couple and I still remember fondly—a perfect mix of rain, laughter, and love."
Submitter: Ariel Quiroz, Live Wedding Painter at Maui Wedding Art
“A groom had placed a large order for customized groomsmen gifts through GroomsDay for his wedding. Everything was going smoothly until, just a week before the wedding, we discovered that there had been a mix-up with the shipping labels. The gifts, which included personalized flasks and cufflinks, were sent to the wrong address—hundreds of miles away from the actual wedding location.
Panic mode kicked in immediately, but instead of focusing on the mistake, we turned our attention to finding a solution. We worked with our shipping partners to track the package and, at the same time, fast-tracked a new set of gifts just in case the original order couldn't be recovered in time.
Thankfully, we were able to intercept the misrouted shipment and expedite it to the correct address just in time for the big day. The groom never even knew there was an issue, and we learned a valuable lesson about double-checking every detail before shipping.
Looking back, it was a nerve-wracking experience, but it taught us how to stay calm under pressure and reinforced the importance of having contingency plans in place. Now, we make sure to triple-check all order details, especially for time-sensitive events like weddings!”
Submitter: Chris Bajda, E-commerce Entrepreneur and Managing Partner, GroomsDay
“It was a lovely spring wedding, and the couple had their hearts set on a stunning venue by the lake. Everything was going perfectly until, just moments before the bride was set to walk down the aisle, I received a call from the transportation company that was supposed to bring the wedding cake. They had gotten into a minor accident, and the cake was destroyed.
Panic set in for a brief moment, but we quickly sprang into action. I reached out to a local bakery nearby and explained the situation, and they miraculously agreed to whip up a replacement on the spot. Meanwhile, we improvised by setting up a beautiful dessert display with cupcakes and cookies, which had been meant as additional treats for guests.
To make it even more special, I arranged for the couple to cut one of the cupcakes, which turned out to be a charming and intimate moment. By the time the new cake arrived—just in time for the reception—no one could tell that we had a last-minute scramble.
The couple laughed it off, and it became a great story they love telling. It was a stressful moment but handling it with quick thinking and a bit of creativity made all the difference.”
Submitter: Grace Thompson, Wedding Planner at ChicSew
“Last year, I had a client's wedding where, despite us offering DJ services, the client insisted on bringing in their own DJ. On the day of the wedding, the DJ they hired showed up late and was not prepared with proper equipment. It caused a delay and disrupted the flow of the event. It was a nightmare for us as planners, but we had to think quickly to find a solution.
Since it was on our client's insistence, they were responsible for the issue. However, we couldn't let it ruin their special day. At the last hour, my team and I gathered all the necessary equipment and set up a makeshift DJ booth. Despite the stress and chaos, we managed to save the day and the wedding turned out to be a success.
Despite everything going wrong, I was proud of my team for coming together and finding a solution instead of panicking. Our quick thinking and teamwork made all the difference in making sure our client's special day was still filled with joy and unforgettable memories.”
Submitter: Carissa Kruse, Wedding Planner and Motivational Speaker at Carissa Kruse Weddings
“Pinning a boutonniere on a tuxedo seems simple enough, right? Well, one eager relative decided to help out and pin the boutonnieres on all the guys. Great idea, but it went hilariously wrong. The groom’s boutonniere was pinned with the pointy end sticking straight out!
Moments before he was set to walk down the aisle, Grandma—a sweet little lady just about chest-high to him—came in for a hug. When she squeezed him, that rogue pin jabbed her right in the face, sending a spray of blood across his pristine white tux!
In a panic, he tried to wipe it off, but all that did was smear it everywhere. With no time to lose, I took a creative route and said, “Let’s turn this into part of the ceremony!” They patched Grandma up and the processional began.
I joked during the ceremony about the blood stains on his coat, saying, “Your family has given their blood, sweat, and tears for this relationship!” The crowd erupted in laughter. It was a wedding to remember!”
Submitter: Alan Katz, Wedding Officiant at Great Officiants
"I was managing a wedding in a large green field. Everything was perfectly arranged, but just before the ceremony, the weather became rainy. We had planned to move the ceremony indoors, but the venue was ill-equipped to handle this shift and we ended up in chaos.
When the guests started to come in, we had to quickly transform the reception area. We rearranged chairs, decorated for the ceremony, and calmed the stressed couple (who we had just met).
The guests ended up enjoying the relatively unorganized program and it became one of the warm stories that the couple still shares with friends. This experience taught me to remain cool and be prepared to bend whenever there are unforeseen circumstances.”
Submitter: Sumit Raghav, Event Planner at NS Events and Exhibitions Fzc.
"I have been in the event industry for almost thirty years and have had my fair share of event planning blunders. One memorable incident was at a high-profile wedding where a sudden storm surprised everyone.
Just as we were about to set up the elaborate outdoor floral arrangements, the sky opened up. It was a chaotic scramble to relocate everything to the indoor venue quickly. In those unpredictable moments, staying calm and adaptable is critical.
We transformed the indoor space into a breathtaking floral wonder, and to my surprise, the bride and groom loved it even more than the original plan. This experience taught me that creativity and quick thinking can turn a challenge into a triumph, reminding us that sometimes, the unexpected can lead to unexpectedly beautiful results.”
Submitter: Kate Hill, Director of Kate Hill Flowers
Conferences are great for discovering innovations, networking with peers, and sharpening your professional development. But sometimes, even the best conferences and events can go awry, leading to some pretty insane stories. Enjoy this reader-submitted list of the best conference disaster stories ever. I'd like to thank my readers for taking the time to share these fun (and cringy) stories with me!
“When I was 24 or 25, a magician I represented double-booked himself and chose a higher-paying event over our kids' birthday party, leaving me no notice.
I called the mother to explain and offered to paint faces or twist balloons for free. She was furious, saying her child had specifically requested a magician. She even threatened to ruin my business if I didn’t send one.
I was pretty new to my career and panicking. I knew magicians and began to make phone calls. Of course, everyone was booked but one, a friend who could tell I was panicking. He invited me over to his house immediately to lend me a few simple tricks.
I showered, went over for a 15-minute crash course, and went to the birthday party to pretend to be a magician. I spent 30 minutes showing guests magic tricks, lying that I had been doing this for "a few years," and speaking to a VERY thankful mom (who I did not tell I was the agent who she yelled at on the phone).
Were the tricks good? Probably not. Was the birthday kid happy? For sure.”
Submitter: Marissa Blaszko, Event Entertainment Agent and Manager at Kaleidoscope Artistic Entertainment
“So, picture this: I’m working a conference, and it’s my first big solo responsibility—managing the event where the current President, George W. Bush is speaking. No pressure, right? I’d spent weeks working with the White House and the Secret Service, going over every detail, and in the days leading up to it, I was at the venue with the advance teams, making sure the staging and lighting were just right. There was nothing left to chance!
The plan was simple: after his speech, President Bush would shake some hands in the front row, then head backstage for a quick photo with the board of directors before jumping into the motorcade and leaving. But there was one big catch—if the board wasn’t ready on time, he would walk out and there would be no photo. And of course, I was in charge of getting them there in place and on time.
So, the moment he finished his remarks, I sprang into action. I rounded up the board and made a mad dash for backstage. I’m in full-on event manager mode, laser-focused, rounding a corner at top speed, when—BAM! I crash right into something. And what or whom did I crash into? The President of the United States.
My heart stopped and I was shaking like a leaf. But President Bush, cool as ever, picked me up off the floor, smiled, and said, 'Darling, it’s alright, there’s no need to rush, everyone’s going to get their photo.' I’m still recovering from the embarrassment to this day, but hey, at least I didn’t get tackled by the Secret Service!”
Submitter: Jennifer Lucio Vargas, CMP, Founder, President and CEO of 305 Communications and Events, LLC
“At a client’s large company retreat, we staged this high-pressure dinner with senior stakeholders and leaders to meet potential investors. The idea was to deliver a luxury dining experience, complete with a carefully designed menu and post-dinner presentation.
Yet, an hour before the event, we learned that the A.V. systems required for the presentation evening didn’t work on the client’s laptops. With so many important people arriving soon, it felt like a potential disaster.
So rather than freak out, we split into two teams. One team searched for alternative gear and the other worked with the speakers to tweak their talks. We communicated the problem directly to the speakers and offered a more conversational style in which they could present informally to smaller audiences. Meanwhile, our tech staff sourced spare equipment. By the time it was installed, the casual negotiations were already underway.
Surprisingly, the clients loved the casual interaction and direct conversations with the executives, which led to deeper, more meaningful discussions. It was a stressful situation, but by staying flexible and focusing on the experience rather than just the plan, we managed to create an even more impactful event.”
Submitter: Jonathan Pickard, Head of Marketing, Holiday Resort Unity
When we first started @designerpartyrentals, we didn’t realize that our beautiful backdrop would fall in very little wind. It did, and it almost broke our $10,000 photo booth!
Thankfully, it landed on grass, so the damage was minimal—only the umbrella for the flash broke while protecting the rest of the booth. I almost had a heart attack when I saw that in action, but it was a great lesson. Now we know to either use large weights or only do indoor events for those types of backdrops!
Fortunately, everyone was happy, and nothing bad happened with the customers. In fact, the incident turned into a funny story that everyone enjoyed, and our clients appreciated our quick thinking. We ended the event on a positive note, with everyone leaving satisfied!”
Submitter: Yeva Syslo, Owner of Designer Party Rentals
“One of my most memorable experiences happened at an industry summit held by our company, which made me deeply understand the importance of improvisation and teamwork.
We held our annual industry summit in a large convention center in Shanghai. We invited over 500 customers and partners. All the preparations went smoothly according to plan and the morning's agenda went very well.
However, it was time for the main forum in the afternoon. The convention center suddenly suffered a massive power outage, and the entire place was plunged into darkness.
Projection equipment and sound system couldn’t be used. Worst of all, the main forum invited a world-famous sustainability engineering expert as a guest speaker. Faced with the sudden technical failure and the confused eyes of more than 500 guests, I felt unprecedented pressure.
After the first few minutes of confusion, my team and I immediately jumped into action. Somebody coordinated with the convention center, while another prepared backup power generation equipment.
We opted for an impromptu conversation with the audience instead of the planned presentation. Face-to-face communication allowed the guest speaker to share his professional insights in greater depth. The audience's interaction with questions was also more enthusiastic.
Many participants later reported that this presentation style was more valuable than a regular speech. This incident taught me to keep calm when facing unforeseen difficulties. Then, you can turn a crisis into an opportunity by using your existing resources and mobilizing your team.”
Submitter: Bruce Zheng, Founder and CEO of NTVAL
“I produced a multi-day ski event in France for a financial client. When the group arrived, about half of the group didn't even ski! I had to quickly plan an alternate itinerary for half of the group, despite not being able to speak French!
I figured out how to get them up and down the mountain every day for planned meals that were ski-in/ski-out restaurants by booking snowmobiles. It was a big curveball, but everyone had a fantastic time! I can laugh about it now.”
Submitter: Breen Halley, Luxury Event Planner at Halley Events
“I’ve had my fair share of unexpected moments while managing events and logistics. One of the most memorable times when things didn’t go as planned was during a large corporate conference in LA.
With just hours to go, some last-minute changes threw our entire logistics schedule into chaos. The transportation we’d arranged for guests fell apart, leaving us scrambling for a solution.
In a pinch, our staff quickly grabbed their phones and started ordering Ubers for all our guests. To ensure the best possible service under pressure, we offered drivers additional tips to provide top-notch experiences.
While it wasn’t our planned solution, quick thinking and adaptability saved the day and allowed us to keep the event running smoothly. Events rarely go perfectly, but it’s how you handle the unexpected that counts."
Submitter: Arsen Misakyan, Co-founder and Event Professional at LAXcar
“One of the most memorable and heart-racing moments in our balloon decorating career took place at none other than the iconic Roosevelt Hotel in Hollywood. We were hired to create a stunning balloon installation for a high-profile client.
Everything was planned out—designs approved, balloons ready, and a timeline that gave us an hour to transform the space once the guests cleared out from an earlier event. Sounds perfect, right? Well, it was...until it wasn't.
As event day approached, the earlier event ran long—way long. We were patiently waiting in the wings with all our supplies, but the minutes were ticking away. Finally, the guests cleared out, and the clock officially started... with just 15 minutes left before the next event was set to begin!
Talk about panic! But we didn’t have time to freak out. Thanks to our preparation and an incredibly talented team, we sprang into action. It was all hands on deck—our balloon artists worked at lightning speed, inflating, twisting, and arranging our signature designs like we were in some sort of balloon Olympics.
By the time the first guests arrived, the room was transformed. They walked into a stunning balloon display, none the wiser that we'd just made event magic happen in a fraction of the time we were promised.
In the end, the event was a huge success, and the client couldn’t have been happier. But it was a reminder of how often venues don’t give you ‘the whole store,’ and you need to be prepared for anything—especially in Hollywood!”
Submitter: Sean Edwards, Founder of The Balloon Guy
“One memorable instance involved a big outdoor event where we had set up several inflatable bounce houses and slides. Everything was going smoothly until a sudden Texas storm hit—out of nowhere! The skies opened up, and the entire area was drenched within minutes.
Obviously, safety is our top priority, so we had to act fast. Our team quickly deflated the inflatables and secured everything to prevent any accidents. We worked with the event organizer to move the remaining activities indoors and helped keep the guests entertained with games that didn’t require equipment.
Luckily, the storm passed after an hour, and we were able to reset everything once it was safe. The kids were excited to get back to the fun, and the parents appreciated how smoothly we handled the situation.
It’s all about staying calm, thinking on your feet, and being prepared for the unexpected. While it wasn’t the day we had originally planned, it turned into a great event, and we learned a lot about managing weather surprises in the process.”
Submitter: Joe Horan, Owner & CEO at Jumper Bee
“I was having an outdoor community event for our residents with food, entertainment, and a chilled-out atmosphere, but unfortunately, the weather was not having it. A sudden rain came down and turned our otherwise sunny celebration into a mud fest.
I knew we couldn't let it ruin the day, so we quickly drew up the team and took it all inside, adapting a new configuration on the fly to keep things lively. I took a microphone, made some jokes about British weather, and assured everyone we weren't letting rain spoil the party.
It wasn't the party we had in mind, but everyone was happy with how we handled it and made the best of it. It also taught me that even when Plan A falls apart, staying resolutely optimistic is half the battle.”
Submitter: Toni Norman, Senior Marketing Manager, Tingdene Residential Parks
As we've seen from these awesome reader-submitted stories, even the most meticulously planned events can take unexpected turns. But it's all in a day's work for our talented wedding and event planners! With a bit of quick thinking, attention to detail, and flexibility, they turned potential disasters into unforgettable moments for their clients. ❤️
Want to ensure your next event is a big success? Download our Entertainment Booking Checklist (form below) to guide you through booking entertainment with confidence.