Celebrity Weddings That Were Almost Derailed By Awkward Moments

A wedding is often billed as the most important milestone in a couple's relationship, if not the most important day in their lives. So, it's natural to want all those hours of planning and money spent to result in a perfect day. Unfortunately, even when both parties are prepared, awkward moments can happen. The only silver lining is that mishaps don't discriminate: They happen at the weddings of the rich and famous just as much as they happen for everyday folks. 

Just ask Blake Lively, whose wedding dress actually caught fire at her reception, or Jennifer Lawrence, who later told the press that she was stressed to the max because her guests were cold. Spending hundreds of thousands — or even millions — on a wedding doesn't ensure that there won't be hiccups, and neither does planning and practicing everything to the final detail. We're sure Princess Diana had plenty of rehearsals before her 1981 wedding to King Charles III, and she still mixed up his name at the altar in front of 750 million spectators. Sometimes, you just can't win, but those imperfections often make everlasting memories and, if nothing else, teach you not to sweat the small stuff. The takeaway, as the following celebrities demonstrate, is that no matter how many awkward moments pop up in your wedding, the show must go on. 

In 2014, Kim Kardashian and Kanye West (now known as Ye) tied the knot in Florence, Italy, officially launching the Kimye era. From the gilded bathrooms to the marble tables, the whole affair reportedly cost a cool $6 million. You'd think that price tag would guarantee a fairy-tale day with no awkward moments, but the couple may have been their own undoing thanks to their first-dance plans. 

For what should be one of the most sentimental moments, the newlyweds were serenaded by pal and legendary croonerJohn Legend for no less than five songs. That's a long time to watch people twirl each other 'round the dance floor, but the Wests were reportedly PDA-ing more than they were actually dancing, leading to an awkward display. An Instagram video later posted by Kris Jenner shows the couple swaying together and kissing until Ye drops his arms, appearing to be over the whole thing.

There were more speed bumps in the road for the Wests, though. "The night before at Versailles, Khloé drank a little too much," Kim revealed on "Jimmy Kimmel Live!" after the wedding (via People). "I had to wake her up and she was laying down sleeping [while] getting her makeup done for the wedding." In addition to one of the most important guests being a little worse for wear, an unidentified guest was a no-show on the day. It happens to everyone, but in Kimye's case, they had every guest's name engraved in said marble tables, so this one was a little awkward — and definitely a mistake you don't want to make with your wedding seating chart.

The thought of a tooth falling out is horrific at the best of times, let alone on your wedding day. Unfortunately, the nightmare came true for Hilary Duff, who wed ice hockey star Mike Comrie in 2010. Recounting the day to Ellen DeGeneres, Duff said that the actual wedding was "perfect," but it didn't get off to the best start. "Beginning part of the day, lost my tooth," she said on "The Ellen DeGeneres Show," adding, "Yeah. Tooth fell out, in my hands. Thank god I didn't swallow it." She shared that she'd been on her bed with her mom and her sister eating bagels at 11 a.m. when she noticed the dislodged tooth. "I burst into tears, and then I started laughing at myself, and then I really burst into tears," the "Younger" actor recalled.

Thankfully, Duff's wedding planner, Mindy Weiss, came to the rescue, with Duff explaining, "Mindy's sister's husband's best friend is like a top dentist in Montecito and called them up." Even more lucky was the fact that Duff had already had a root canal on the missing tooth, so there was little physical pain involved. In the end, Duff noted that because her tooth falling out was "the worst thing that could possibly happen," it actually left her pretty relaxed and hopeful about the rest of the day.

While Blake Lively and Ryan Reynolds' story is often revered as romantic, the 2012 South Carolina wedding that kicked off their married life ran into a few hurdles, beginning with Lively watching her stunning Marchesa gown nearly go up in flames at the reception. "Florence Welch [of Florence & the Machine] was singing at the reception, and they brought out these sparklers ... " she told Vogue in 2014. "I look down and my wedding dress has a big burn mark from one of the sparklers. Right on the front!"

Though Lively was understandably shaken by seeing her dress marked by embers, Reynolds knew exactly what to say to cheer her up: "Later, my dress was hanging up and Ryan said, 'Isn't that beautiful?' ...  And he pointed to the burn. My heart just stopped, because it was such a sensitive little subject. And he said, 'You'll always remember that moment with Florence singing and the sparklers ...' Now that's my favorite part of the dress."

While the burn may have been a blessing in disguise, the couple's nuptials were overshadowed by their venue: Boone Hall Plantation and Gardens, a site of suffering for enslaved people."It's something we'll always be deeply and unreservedly sorry for," Reynolds told Fast Company in 2020. "It's impossible to reconcile. What we saw at the time was a wedding venue on Pinterest. What we saw after was a place built upon devastating tragedy."

Under normal circumstances, walking down the aisle is nerve-racking, but a royal wedding, with hundreds of millions of live spectators and centuries of tradition to live up to, is enough to make even the calmest person fumble. And that's exactly what happened to the late Princess Diana when she married King Charles III (then Prince Charles) at St. Paul's Cathedral in 1981. The wedding has gone on to become one of the most iconic in history, but it wasn't free of awkward moments, beginning with Diana mixing up the name of her betrothed. "I, Diana Francis," the priest told her to say (via CBS News). "Take thee, Charles Philip Arthur George." But instead, Diana said, "Philip Charles Arthur George." In her defense, he has four names, and many people forget that Diana was just 19 years old at the time.

The royal wedding had its share of other mishaps, too. After squishing her taffeta gown's 25-foot train in the royal carriage, Diana arrived at the cathedral with a few wrinkles on her dress, which left designer Elizabeth Emanuel "horrified" (via Brides). It wasn't the only wardrobe malfunction, either — Diana also spilled perfume on her dress in the morning, creating a stain that she had to hide with her hand throughout the day. Even still, the gown was one of the most iconic Princess Diana outfits recreated by "The Crown," and despite these hiccups, the world only remembers the fairy-tale wedding that defined a generation.

The mark of a successful wedding is the couple enjoying themselves, but still, some newlyweds will be more concerned with how their guests are feeling. In fact, "The Hunger Games" star Jennifer Lawrence was so worried about her guests that it actually ruined her 2019 wedding with gallery director Cooke Maroney. "I'll never forget — I was freaking out about the guests being cold and all of my friends were lying they're like, 'Nobody's cold, nobody's cold, everything's fine, everything's fine,'" she told E! News at the 2024 Golden Globes, adding that her mom later admitted that it was, in fact, "freezing."

It's understandable that Lawrence was so worried about her guests during her wedding festivities since one of the rehearsal dinner attendees was none other than legendary actor Robert DeNiro, who didn't know many people there. "So I looked over and I saw Bob, who doesn't know anybody. And he's kind of wandering around, and I was immediately just like, 'No.'" Lawrence admitted that she told DeNiro that it was okay for him to leave, which made her "feel better." In hindsight, she looks back on the experience as "so stressful" and "awful."

Chrissy Teigen and John Legend are one of Hollywood's favorite couples, but their charmed married life didn't get off to the best start. The potential for the perfect wedding day was there: It was 2013, and the A-lister pair decided to tie the knot in Italy's picturesque Lake Como after briefly thinking about a rural wedding at home. Unfortunately, storms raged in parts of the U.S. at the time, which meant that the couple's family and friends flying to Italy from Ohio were delayed. Teigen and Legend decided to postpone the nuptials for a few hours until everyone was there. Fortunately, the waiting game wasn't all dreary. "They had cocktails for four hours!" Teigen told Martha Stewart Weddings (via People).

Despite a bumpy start, the rest of the wedding went according to plan, but there was still one aspect that Teigen looked back on with regret. "And that's not having a first dance," she admitted to The Insider in 2014, per Bridal Guide. "I refused to have a first dance 'cause I can't dance. So I don't like dancing in front of people. But everything else was just perfect."

Each Kardashian wedding is bigger than the last, so we weren't surprised by the grandeur that accompanied Kourtney Kardashian's 2022 nuptials to Travis Barker (it may have even led to over-the-top weddings soaring in popularity in 2023). Part of the festivities took place in the romantic setting of Portofino, Italy, but as Kourt made her way toward the aisle, her hand-embroidered cathedral-length veil got stuck. The eldest Kardashian sister didn't do herself any favors by including a set of steep, rocky stairs in her route to the makeshift altar, but she did handle the mishap like a pro by pausing briefly until the situation was corrected and then carrying on. She may have also anticipated a veil-related fumble since she had staff on hand to hold the delicate material.

The couple's wedding was otherwise a spectacular affair, but again, it wouldn't be a Kardashian event without a little drama sprinkled in for good measure. Six months after the wedding, Kim Kardashian announced a business collaboration with Dolce & Gabbana, the fashion house that had designed Kourtney's wedding looks and also provided an exclusive seaside villa for the location. "It feels awful that my sister used my wedding as a business opportunity," Kourtney said in an interview on "The Kardashians" before admitting to Kim's face, "It was such a special day. I feel like it takes away from the specialness."

Another lavish affair where no expense was spared, the 2022 nuptials of Brooklyn Beckham and Nicola Peltz were surrounded by rumors of tension between Nicola and the Beckhams, which may have come to a head at the reception. If the gossip is to be believed, hostility between Nicola and Victoria Beckham, in particular, may have started when Nicola didn't wear one of Victoria's designs as her wedding gown despite previously allegedly agreeing to let her future mother-in-law dress her. But Victoria was also reportedly barred from helping with the wedding planning, and the top table at the reception was said to be a Beckham-free zone, reserved for the Peltz family only. This all supposedly accumulated in an awkward moment that sent the bride running off in tears.

"Marc Anthony, who is a friend of the Beckhams, offered to perform as a gift at the wedding," an insider told People. "Before the song began, Marc Anthony asked Brooklyn to come to the stage, and then announced, 'The most beautiful woman in the room tonight, come on up ... Victoria Beckham!'" Another source revealed, "It was such a jaw-dropping moment that it left the whole room in absolute shock." Meanwhile, another wedding guest maintained that this moment came later in the evening after the newlyweds had had their first dance, so it wasn't as dramatic as the reports say. Regardless of what went down, Nicola has told the press on several occasions that there is no feud, but rumors reignited when she and Brooklyn were noticeably absent from David Beckham's 50th birthday celebrations in 2025.

In 2014, "Once Upon a Time" star Ginnifer Goodwin tied the knot with co-star Josh Dallas, much to the delight of the show's fandom. Chatting about her nuptials to Jimmy Kimmel, Goodwin revealed that most of the day had been "stress-free" and "beautiful," but one major hiccup had nearly thrown the whole wedding off course. "We hired a wedding planner to help us ... and she called me crying on the morning of our wedding," Goodwin recounted to Kimmel (via HuffPost). "She said, 'My car has been robbed.'"

During the theft, the robber had taken the ketubah, a sacred Jewish marriage contract that binds the couple by religious law. Dating back to ancient times, the ketubah is an important part of many Jewish wedding ceremonies, with many modern versions being handwritten in Hebrew before becoming home displays following the big day. So, understandably, it was a big deal that this went missing. But thankfully for Goodwin and Dallas, the stars aligned. "Two Jews were walking down the street in Hollywood, found a piece of paper in the middle of the street, read Hebrew ... and got us back our wedding ketubah," Goodwin explained.

Many celebrities happily get married later in life, and Cameron Diaz is one such star who found her happy ending on her own time, rather than settling or rushing into such an important decision. Her patience paid off, and she found the man of her dreams in Good Charlotte musician Benji Madden. The 2015 wedding was gorgeous, but not without a few awkward moments.

For starters, the lights unexpectedly went out just as Diaz was about the walk down the aisle. The wedding took place at the couple's mansion in Beverly Hills, and was left in darkness for 10 seconds (which in all fairness would feel like a lot longer when you're about to make your bridal entrance), so Diaz reportedly freaked out. The lights came back on, and Diaz was able to walk down the aisle as planned. But when it was time for the rings, 5-year-old Sparrow Madden, Benji's nephew, had a moment of his own. "He dropped the ring and it rolled around," a source shared with the Daily Mail. "The audience began to chuckle. But as both brothers — groom Benji and best man Joel — got on their hands and knees looking for it, the guests broke out into full laughter." There's no right or wrong way to wear your wedding rings, but said rings do need to make it to the couple!

The Kardashian-Barker wedding festivities took place across three separate events: They kicked things off with a rockstar-style Las Vegas wedding in April 2022 before legally getting married in Santa Barbara that May, just ahead of their extravagant Italian ceremony. It's lucky they had the Portofino party since their Vegas wedding came with a few hurdles.

For starters, the Elvis impersonator who married them called Kourtney Kardashian-Barker "Khloé." In "Keeping Up with the Kardashians" footage from the wedding, Kourtney can be heard jokingly saying "I'm gonna cry" before falling onto the floor. Kourtney later admitted that she was intoxicated during the events and couldn't remember much. "Once upon a time in a land far, far away (Las Vegas) at 2am, after an epic night and a little tequila, a queen and her handsome king ventured out to the only open chapel with an Elvis and got married (with no license)," Kourtney wrote on Instagram.

As one of the biggest stars of the '80s, Madonna's 1985 nuptials with longtime actor Sean Penn unsurprisingly attracted widespread media attention. But the swarms of paparazzi outside the Malibu location nearly ruined the day when they got in the way of the "Like a Virgin" singer's designer, Marlene Stewart, transporting the all-important dress to the pop star.

"The roads were inaccessible because the press were everywhere," Stewart told Best magazine (via Rolling Out). "But the police stopped me! I insisted I had to get through. There were no cell phones, so you had pagers and I was just trying to page somebody!" Luckily, Stewart was able to get through and deliver the dress on time, but the chaotic situation may have influenced Madonna's next nuptials, which were to film director Guy Ritchie in 2000. The couple's choice of a private and remote setting in the faraway Scottish Highlands kept the press and ensuing police presence to a minimum.

Speaking of awkward moments, check out these times celebs wore inappropriate outfits to other people's weddings.