The Biggest Celebrity Wedding Disasters We Still Can't Get Over

Celebrity weddings may look flawless on glossy magazine pages. But beyond the designer gowns, star-studded guest lists, and surreal venues, they can be just as unpredictable as any regular wedding. When a celebrity flubs their wedding vows or the lights go out before their bridal entry or wedding guests arrive unimaginably late, these goof-ups serve as pertinent reminders that behind the veneer of PR-managed perfection that audiences are fed, these A-listers are as human as the rest of us. 

As anyone who has ever been to a wedding before will testify, it's in these very moments of chaos and damage control that a majority of wedding memories are made. We weren't there, but we can bet that Bethenny Frankel won't ever forget peeing in a bucket at her wedding. Or that Freddie Prinze Jr.'s guests might still recall narrowly escaping a hurricane and an earthquake at his wedding. Here are some of the biggest celebrity wedding disasters we still can't get over. 

Hilary Duff was all set to tie the knot with hockey player Mike Comrie in 2010. But before she could walk down the aisle, she suffered an unexpected mishap that could well have been a gag from "Lizzie McGuire." She broke a tooth. "Thank God I didn't swallow it," she said on "The Ellen DeGeneres Show," recalling her wedding-day nightmare. Duff was apparently eating a bagel when the dental emergency occurred. "I was sitting on the bed with my mom and my sister, and they were like, 'You're an idiot, you did not. Come on!'"

Though the incident set Duff off on a rollercoaster of emotions, she didn't let it ruin her big day. With a few hours to go until the wedding, she managed to call a dentist who restored her smile in time. Duff also texted a picture of her toothless moment to her soon-to-be husband before the ceremony, joking: "You're ready to marry me?" The wedding itself was a bit of a blur for Duff, who had to see to a hundred guests and barely had time to eat or drink. Despite all the chaos — or maybe because of it — the wedding, in Duff's words, was perfect.

When Kate Upton and Justin Verlander decided to tie the knot, they could hardly have imagined that a baseball game would get in the way of their special day. But that's probably what happens when one half of the pair is universally revered as one of the best pitchers the sport has ever seen. The celebrity wedding in Tuscany coincided with the seventh game of the World Series, in which Verlander's team, the Houston Astros, was scheduled to play. 

In what can only be described as a bizarre mix-up straight out of a comedy, Upton and Verlander were in the United States, while their families were all the way over in Italy, enjoying their wedding festivities without them. "We had an event that night, and everyone's texting us like, 'Your wedding's so pretty, wish you were here,'" Upton recalled on "The Tonight Show Starring Jimmy Fallon," while Verlander added: "We got taken around our wedding via FaceTime." To add to their celebrations, the Astros won that game, after which the couple promptly jetted off to Italy to say their "I dos." 

Love was definitely in the air at Jessica Simpson's wedding. But so was quite a bit of nervousness. At her 2014 nuptials with Eric Johnson, the singer — who had by then conquered world stages, topping charts, and stealing hearts everywhere — delivered a less-than-perfect performance during her wedding vows. It happens to the best of us, apparently. In fact, Simpson was so overcome with emotions that she ended up saying her own name in the speech, instead of addressing it to Johnson (via E! News). 

This sweet flub was outdone, if at all, by Johnson, who got so overwhelmed himself that he had to restart his vows after being unable to get through it the first time. Later, the groom reiterated the emotional intensity of the ceremony in an interview with People, saying: "I saw my gorgeous wife coming towards me and she was crying. ... I think my heart was exploding a little bit." However, after over 10 years of marriage, Jessica Simpson and Eric Johnson divorced in 2025. 

Beachfront weddings aren't always the fairy tales they are made out to be. Case in point: Sarah Michelle Gellar and Freddie Prinze Jr.'s wedding in 2002  weathered not one, but two natural disasters. The couple's ceremony in Puerto Vallarta, Mexico, was first somewhat derailed by the arrival of Hurricane Hernan. With winds picking up and storm clouds overhead, the couple had to move the party indoors at the last minute. The super private wedding was off-limits to the paparazzi, but those who did manage to hang around the venue described the frightful conditions that prevailed.

"[W]e faced towering waves and gusts of gritty wind," wrote one reporter in the Independent. "This threatened to evolve into the kind of disaster I was used to reporting." While the upheaval of Gellar and Prinze Jr.'s special day seemed to have passed, nature had one more surprise in store. The next day, as guests were leaving, the region was rocked by a 4.6-magnitude earthquake. Still, the couple rode the chaos out peacefully; and in the words of a family friend of Prinze Jr.'s: "All of those bigger-than-life natural events can only bode well for the marriage" (via People).

Kristin Cavallari's wedding-day disaster was so surreal it almost sounds made up. On the morning she was set to marry NFL player Jay Cutler, the "Laguna Beach" alum was bitten in the face by her own dog. As detailed in her memoir "Balancing in Heels," Cavallari was spending time with her family on her big day when Brando, her furry companion, snapped and bit her right near her eye. 

"I put my head down by Brando, and next thing I know, I'm sitting up in pain, realizing that the hand I'm holding to my face is covered in blood," she wrote. Though Cavallari's description of the mishap made it sound catastrophic — "All I saw was a swollen eye and blood everywhere" — it was thankfully salvageable. With a little bit of improvisation and makeup, Cavallari was able to get through her wedding day without further hiccups. The 2013 wedding was her second attempt at marrying Cutler, after calling off their engagement the first time around in 2011. 

John Legend and Chrissy Teigen legally wed in a courthouse before taking their grand celebrations to Lake Como. But what should have played out like a romantic Italian fairy tale was put to the test by stormy weather in the United States, from which many of the couple's relatives were flying to the ceremony. Despite running four hours behind schedule, Teigen and Legend did not want to proceed with their nuptials until the guests arrived, so they decided to hit pause on the event. 

Fortunately, for the rest of the attendees, cocktails flowed freely during this long wait, and staying busy was not an issue. However, it seems that Teigen was initially kept in the dark about the chaotic delay. "I wasn't even aware of it because everyone wanted to keep it a secret from me. They didn't want to stress me out," she told The Knot. When Teigen and Legend's loved ones finally made it, the couple pulled off their long-awaited ceremony against a dreamy lakeside backdrop. Picture perfect as it was, Teigen later admitted that she could have done a few things differently, from writing better vows to having a first dance. 

Martine McCutcheon, of "EastEnders" and "Love Actually" fame, tied the knot with her beau Jack McManus at a dreamy destination wedding in Lake Como in 2012. In that kind of picture-perfect setting, the last thing anyone could have expected was for the bride's attire to have gone up in flames. Unfortunately, that's exactly what happened because, in the words of McCutcheon herself, "There's always something that goes wrong" (via Hello!). The disaster played out in a matter of seconds during their reception, when the newlyweds each took their turn to speak.

"[M]y husband set my veil on fire when he put the microphone down on the table, then I had to reach over the candelabra to reach the microphone and get it," McCutcheon recalled. "And you literally see someone's hands in the video, like putting out the fire on my veil." Considering that no amount of practice can probably ever close the gap between wedding rehearsals and the actual ceremony, McCutcheon did admit to wishing that she had been less swept up in the chaos of the day. And speaking from personal experience, she dished out some sound advice to brides. "I would say, enjoy the process and nothing's ever perfect on the big day," she offered.

Princess Diana's 1981 wedding to King Charles III is often remembered as one of the best royal weddings in history, leaving 750 million viewers around the world in awe. Fairy-tale gown, glittering tiara, traditional royal grandeur — it had all the makings of a real-life fairy tale and ended up looking flawless on television. It was only after the wedding that details started spilling of just how chaotic the whole affair was behind the scenes, which, over the years, has lent it a far less magical reputation. 

For starters, and most importantly, Diana was not happy. A 2017 National Geographic documentary, "Diana in Her Own Words," records the late princess calling her wedding "the worst day of my life" and sharing how she confided in her sisters about her hesitations over marrying Charles. With this grave shadow of doubt hanging over the event, a string of other things went wrong on Princess Diana's wedding day. Her iconic wedding attire was all over the place; there were perfume stains down the front of the dress, which was visibly wrinkled, and the bride was apparently suffering from a splitting headache, courtesy of the tiara on her head. In what was perhaps one of the biggest flubs from the wedding, Diana also said her soon-to-be husband's name wrong during the vows, messing up the order of his titles. 

Is a wedding even fun if it doesn't come with some drama? Emmy Rossum had one such tale to tell when she appeared on "The Late Late Show With James Corden" after tying the knot with director Sam Esmail in 2017. But her wedding-day gossip wasn't courtesy of tipsy speeches or wardrobe malfunctions, but instead, feuding flower girls who all but upstaged the "Shameless" star. Right before Rossum made her grand entrance in a stunning Carolina Herrera gown, her bridal party members who walked down the aisle had their own plans.

"It was during their nap time, so one of the girls was quite cranky and not feeling it at all," Rossum recalled. "The other girl was quite a diva about it. She was really having her moment. And when the nappy, cranky girl noticed that the diva girl was getting quite a lot of attention, she ran up the aisle and began throwing her petals very aggressively at the other girl." The chaos of it all likely added to the memorability of the event, with even the rabbi remarking to Rossum: "You're lucky you're famous because these girls really just stole your spotlight."

In the timeline of the long and complicated history between Sean Penn and Madonna — whose short-lived marriage is still pop-culture legend — one particularly tumultuous episode stands out. It goes back to their wedding day in 1985, when the power couple was all set to tie the knot in a very private ceremony in Malibu. Much as the couple tried to keep their ceremony under wraps, privacy was unfortunately never really an option, considering the blinding stardom and media interest that defined their relationship. 

The paparazzi surrounded Penn and Madonna's wedding venue in many directions, including in helicopters. According to Rolling Stone, such was the intrusion that the couple couldn't hear each other's vows over the noise and flipped off the overhead paparazzi while making their promises of love. The bizarre scene only got more surreal when Penn, whose reputation as a foul-tempered Hollywood bad boy preceded him, whipped out a gun and fired shots in the sky. "I would have been very excited to see one of those helicopters burn and the bodies inside melt," he notoriously remarked later.

Just hours before she tied the knot with Josh Dallas in 2014, Ginnifer Goodwin received a call that no bride wants to get on her special day. Her wedding planner's car had been robbed, and among the things stolen was the couple's ketubah — a marriage contract central to Jewish weddings. At that point, Ginnifer Goodwin's wedding could have been a catastrophe, but instead of losing her cool, the "Mona Lisa Smile" star showed impressive composure and immediately began spitballing alternative options. "The rabbi's at a hotel. I'm sure there's stationery there. We'll be fine. This is not a big deal," she recalled on "Jimmy Kimmel Live!" (via ABC News). 

What happened next could have been a scene straight out of one of the many rom-coms in Goodwin's oeuvre. Goodwin got a call from her team informing her that two Jewish people had come across a stray piece of paper somewhere on the streets of Hollywood and, given their ability to read Hebrew, recognized that it might have been an important document. As Goodwin recalled, the pair promptly "Googled who represents Ginnifer Goodwin, found my reps at home on a Saturday, and got us back our wedding ketubah."

When nature calls, even brides in couture gowns have no choice but to answer. For Bethenny Frankel, that moment arrived just minutes before her wedding to Jason Hoppy commenced, when she was all ready and decked up in her beautiful bridal dress ... and seven months pregnant. So she did what any reality TV star worth her salt would have done and hiked up her gown to do her business in a champagne bucket. 

As if the shock factor of the incident alone wasn't enough, her bathroom break played out with the cameras rolling for her Bravo spin-off "Bethenny Ever After." It was the kind of bold stunt only Frankel could spin into television gold. "I showed the little minutia like what happens when you have to pee and you're seven and a half months pregnant and you have to walk down the aisle," she later told ABC News, agreeing that while it may not have been the classiest move, given the setting, it had been her only option in that moment.