11 Marriage Proposal Mishaps

Dwight and Mamie Eisenhower photographed in 1957.
Dwight and Mamie Eisenhower photographed in 1957. / L. Waldorf/Evening Standard/Hulton Archives/Getty Images

Ahhh, the marriage proposal. Never has a tradition been surrounded by so much anxiety and planning, and the potential to be embarrassing and, well, even downright cringe-worthy. In these 11 proposals, there’s nudity, dorky costumes, two highly damaged properties, ill-timed urination, a lost ring, and an answer that arrived a year too late—and yet they still somehow all turned out OK. So maybe these will serve as inspiration, or a way to drum up a bit of courage ...

1. Jumbotron Gone Wrong

Baseball game proposals are pretty standard, and everyone loves seeing the happy couple on the jumbotron. But back in 2011, a 28-year-old man named Jonathan told Cosmopolitan about how he unwittingly struck out when it came to his ballgame proposal to his then-girlfriend, Sarah. He scored tickets to the baseball game, called the arena ahead of time, and paid to have “Sarah, marry me” flash across the screen. In the third inning, when Sarah got up to use the restroom, Jonathan didn’t worry because he had been told that the proposal would happen between the fourth and fifth innings. But as he was sitting there waiting for Sarah to return, his proposal flashed across the screen, and the camera panned to their seats. And the whole stadium saw him sitting there ... alone. "I asked her anyway, but it wasn't quite the surprise I had hoped for," he said. Hopefully he got a refund on the jumbotron fee.

2. All Sands on Deck

Megan Fox and Brian Austin Green photographed in 2014.
Megan Fox and Brian Austin Green photographed in 2014. / David Livingston/Getty Images

Brian Austin Green and Megan Fox are no longer married, but when the Beverly Hills, 90210 star proposed to Fox on a beach in Hawaii in 2010, she immediately said yes ... and then they lost the ring. "I saw her jumping up and down," a witness told US Weekly. "Later, I saw a half dozen staff sifting through the sand." After two hours of searching, what was described as the “two-carat sparkler” still hadn’t been found. Presumably it just took a little more than those two hours, because it’s doubtful the staff at the Four Seasons Resort Hualalai stopped looking.

3. Say Anything, and Two Cranes

A man in the town of IJsselstein in the Netherlands rented a crane for the purpose of hoisting him up outside his significant other's bedroom window, so that he could play a song, Say Anything-style, then pop the question. Unfortunately, the crane crashed into the building and demolished a neighbor’s apartment. Fortunately, nobody was harmed. If you thought the situation couldn't get worse, think again: When a larger crane was brought in to carry out the smaller crane, six more apartments were damaged in the process. According to the Dutch newspaper Algemeen Dagblad, “the girlfriend said yes anyway.”

4. Gee Whiz

Michigan resident Kevin Przytula took his girlfriend Allyssa, along with Allyssa’s 3-year-old son Owen, to Bay City one weekend in 2018 to propose. Przytula dropped down on one knee in front of a fountain, and, in the background, Owen dropped his drawers and began to pee. The moment was caught on camera by Kevin and Allyssa’s family members, and the moment went viral. Owen was dubbed “The Whiz Kid.” Fortunately, Przytula didn’t realize he was being upstaged by the youngster until after he had finished the proposal. “Oh my God he’s peeing, are you serious?” Przytula said, giggling once he saw the video. Allyssa wasn’t as surprised. “I just started laughing," she said. "This is what Owen does."

5. Fellowship at Fazoli’s

As part of a 2017 Insider compilation of funny proposal stories culled from the internet, Redditor Thousands_of_Spiders recalled a very stilted proposal they witnessed at the casual Italian dining chain Fazoli’s. A man dressed like a knight walked in, carrying an actual sword affixed to his hip. The woman with him, wearing regular clothes, looked uncomfortable. The knight made an announcement: "HEY EVERYONE! We're getting married! I just asked this beautiful girl to marry me and she said yes!"

"While they wait in line to order their reasonably-priced pasta dishes, his friends begin to file in,” Thousands_of_Spiders recalled. “They were all driving from the movie theater where they had just met to see their friend pop the question at the premiere of The Lord of the Rings: The Fellowship of the Ring.

"She ate her food in silence while he and his friends recapped the movie loudly. She looked like she was going to cry."

6. Burnin’ Love

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In August 2020, Albert Ndreu spent hours setting up his apartment in Sheffield, England, to make sure he had the perfect backdrop for his proposal to Valerija Madevic. Soft music was playing, a bottle of Chianti was at the ready, 60 balloons were strewn throughout his home, and 100 candles spelled out “Marry Me?” Ndreu left to pick up his soon-to-be fiancée, but when they returned they found a heavy fog of smoke. The fire department was called, but not before the apartment was gutted by a fire. Despite the property damage, Ndreu still got down on one knee and proposed. “He said that he messed up—our house was literally in flames—but asked me if I would marry him,” Madevic said. “And I said yes."

7. Class In Two Acts

When Dwight Eisenhower, the future President of the United States, proposed to his wife-to-be Mamie in 1916, he chose a somewhat unconventional piece of jewelry for the ring: a miniature version of his class ring from West Point. Tradition had long dictated that a West Point grad's fiancée wear a mini replica of his class ring as her engagement ring, but Mamie wasn’t having it. She wanted "the real thing," meaning a full-size version of the ring—which she got. In fact, it was that duplicate version of Ike's class ring that she wore throughout their life together, with the exception of when she accompanied her husband on the presidential campaign trail in 1952. According to Mrs. Ike: Memories and Reflections on the Life of Mamie Eisenhower, written by their granddaughter Susan Eisenhower, Mamie took her ring off when she knew she'd be shaking a lot of hands, as the ring was large and heavy and often left her hands black and blue.

Dwight made a second unfortunate miscalculation when he proposed by choosing to pop the question on Valentine’s Day. While there's nothing wrong with proposing marriage on February 14, Dwight was a traditional kind of guy and felt the need to ask Mamie's father for his blessing. But her dad was out of town on business, so Mamie's mother refused to let her wear the ring until Dwight had gotten his future father-in-law's consent. He wasn’t able to do that until more than one month later, on March 17. After that, Mamie would always celebrate both Valentine’s Day and St. Patrick’s Day as her engagement anniversaries, presumably receiving flowers for both.

8. Total Knockout

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Kyle Pierce planned to propose to his girlfriend Jenna Eller in the middle of her volleyball match at Concordia University in Seward, Nebraska. However, as he strolled out onto the court to propose, Eller ran to hit the ball but smacked into Pierce, sending her crashing to the floor. Fortunately, she dusted herself off, and wasn’t very upset. He dropped to one knee, holding up a volleyball on which he had written “Will You Marry Me?” She happily said yes.

9. Breast-Case Scenario

Seth Rogen’s proposal to Lauren Miller was quite unintentionally risqué. The actor was so excited about asking Miller to marry him that he completely forgot about any elaborate plans as soon as he had the actual ring in hand. “I was just so nervous when I got it,” he recounted on Conan. “I couldn’t have a conversation with my girlfriend, all I could think was this ring, ‘Don’t mention Lord of the Rings, don’t say anything about a ring.'"

He went upstairs to their bedroom to propose to her, but she was in the closet changing and was, um, only half dressed. “I was like ‘Oh man, her boobs are out, that’s not part of the plan,’” Rogen said. “I didn’t picture it like this and I know she didn’t picture it like this.” The couple has been married since 2011.

10. Love's Letter's Lost

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In an essay that conjures images of a John Wayne movie, John Taylor wrote a story for Reader’s Digest about his grandfather, John Toner, an 1880s cowboy, and his grandmother Margaret’s wedding. John asked Margaret to marry him before setting out on a 90-mile trek across the desert to work over the summer on a Colorado ranch. Margaret said she would think about it, and send him a letter with her reply. However, no letter ever arrived.

At the end of the summer, Toner rode back into town thinking Margaret had rebuffed him, only to meet up with her brother, who told him, "Toner, get out of here. You’re no longer welcome." Turns out Margaret had sent him a letter with the date for their wedding—which he had missed! Margaret and her family eventually forgave John, and the two were married. The next summer, Margaret’s letter arrived in Colorado ... almost exactly one year late.

11. The Fifth Time Is a Charm

Joe Biden had to propose to Jill five times before she would say "yes."
Joe Biden had to propose to Jill five times before she would say "yes." / Public Domain, Wikimedia Commons

On December 18, 1972, just a few weeks after he was elected to the Senate in Delaware, Joe Biden's wife Neilia and their 1-year-old daughter Naomi were in a fatal car crash when their vehicle was hit by a semi-trailer truck. The Bidens's sons, 3-year-old Beau and 2-year-old Hunter, were also in the car but survived with relatively minor injuries.

Three years later, Joe's brother Frank set him up on a blind date with Jill Jacobs, a college student nine years Joe's junior. Though Jill was only in her early twenties, she had already been married once and was in no rush to do it again. "Marriage meant something different to me by that point," Jill wrote in TIME. "I knew that it was harder to unite two lives than I had imagined growing up. I knew that relationships could be fragile. I knew that, no matter how much I tried, there would be so much that I couldn’t control. If I gave Joe my whole heart, he had the power to break it. What if he changed his mind? What if it didn’t work? What if I took another chance, and I was left humiliated? What if I failed?"

Which helps explain why now-President Biden had to propose to Jill a total of five times before she said yes. The first proposal came after Beau and Hunter cornered their dad and told him, "We think we should marry Jill,” understanding that, in some ways, it was a family decision. But Jill, who also worried about living a life in the spotlight, still wasn't convinced. So Joe was patient with her ... until he decided he couldn’t be anymore after his fifth proposal. He went on a congressional trip to South Africa and told her he needed her answer when he returned. Fortunately, she said yes.