Hilary Duff & Mike Comrie

Imagine waking up for your wedding day: skin perfect, makeup all ready, and your party starts coming in to help, and then you lose a tooth. That’s exactly what happened during Hilary Duff’s wedding to Mike Comrie. While eating a bagel, one of her teeth popped out before the ceremony. However, her wedding planner got her an emergency dental appointment and it was all fixed up in time.

Kate Upton & Justin Verlander

Kate Upton and Justin Verlander’s joint appearance on The Tonight Show Starring Jimmy Fallon in 2017 sheds light on their Italian wedding. They actually ended up missing their wedding for the World Series, but ended up joining their nuptials via Facetime.

Emmy Rossum & Sam Esmail

During her interview on The Late Late Show with James Corden, Emmy Rossum revealed that during her wedding with Sam Esmail, her flower girls nearly stole the show.

“It was during their nap time, so one of the girls was quite cranky and not feeling it at all, and the other girl was quite a diva – she was really having her moment,” she started. “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.”

She added, “Then when I got up there the rabbi was like, ‘Wow, you’re lucky you’re famous because these girls really just stole your spotlight.’ Then the rabbi made some joke like, ‘It just goes to show there’s always someone younger and cuter coming down the aisle.’”

Bethenny Frankel & Jason Hoppy

During her 2010 wedding to Jason Hoppy, Bethenny Frankel had to pee in a bucket because there was no toilet nearby. Luckily, her friends helped out and the wedding went off without a hitch!

JFK Jr & Carolyn Bessette

JFK Jr and Carolyn Bessette went to great lengths to make their wedding private. In fact, his assistant RoseMarie Terenzio set up a fake itinerary, which caused the paparazzi to go on a wild goose chase, per E!

Chrissy Teigen & John Legend

Chrissy Teigen and John Legend had to postpone their wedding for four hours to accommodate family members who were running late due to delayed flights. 

Eric Johnson & Jessica Simpson

Eric Johnson and Jessica Simpson’s wedding almost went perfectly. Almost. When they were exchanging their vows, Simpson accidentally said her own name instead of Johnson’s.

Ginnifer Goodwin & Josh Dallas

When Ginnifer Goodwin and Josh Dallas got married, there was a thief! Their wedding planner revealed that someone broke into her car and stole their ketubah (their traditional Jewish wedding contract). Luckily, two good samaritans found it and returned it to them, per HuffPost. 

Sarah Michelle Gellar & Freddie Prinze Jr.

Sarah Michelle Gellar and Freddie Prinze Jr faced two major issues during their wedding: Hurricane Herman the day of, and then an earthquake happened the day after, per People.

Sean Penn & Madonna

When Sean Penn and Madonna married on Aug. 16, 1985, they tried to do everything to evade the paparazzi. Along with saying some curses at them in the sand, Penn allegedly started to shoot at them?! And apparently, per EW, he even said ”I would have been very excited to see one of those helicopters burn and the bodies inside melt.”

Olivier Sarkozy & Mary-Kate Olsen

So for drama that infuriated everyone else, we need to talk about Olivier Sarkozy and Mary-Kate Olsen alleged decorations for their wedding. According to the New York Post, they had “bowls and bowls filled with cigarettes” throughout their wedding. 

Kristin Cavallari & Jay Cutler

Something mortifying happened to Kristin Cavallari on her wedding day to Jay Cutler: she was bitten by their dog. Not only that, she was bitten on the face, and per EOnline, her makeup artist ended up gluing the cuts shut.

Blake Lively & Ryan Reynolds

During Blake Lively and Ryan Reynolds’s wedding had quite a few dramatic moments. First off, during the wedding, Lively’s dress caught on fire after a sparkler got on it, per DailyNews, and then years later, they found themselves in controversy after fans discovered they married on a reservation.

Jennifer Lawrence & Cooke Maroney

Jennifer Lawrence revealed that her wedding day to Cooke Maroney wasn’t so fun. She said on the red carpet at the Golden Globes, “It’s so stressful. You’re not having fun. You’re just like, ‘Is that person having fun?’” 

She added, “And all of my friends were lying they’re like, ‘Nobody’s cold, nobody’s cold, everything’s fine, everything’s fine. My mom was like, ‘It’s freezing out there, your grandmother almost died.”

Princess Diana & King Charles

Not only did royal writer Ingrid Seward’s claim in her book My Mother And I that Princess Diana’s father, Earl Spencer, ultimately convinced Diana to marry Charles after she had doubts, but Sweard claimed Diana was in despair the whole time.

“Diana was in despair. Her fiancé had been away in America for most of the previous week, yet he clearly had no desire to dance with her,” she said. Elton John was performing, people were dancing, and yet Charles spent most of the night “dutifully working the room and making sure he spoke with as many people as possible.”