These Awful Celebrity Marriage Proposals Will Make You Cringe

Imagine being a beloved celebrity in a beautiful, happy relationship. Then imagine the marriage proposal being a huge flop. Believe it or not, it happens.

No one is perfect, and sometimes proposals just don’t go according to plan. It’s easy to feel jealous of celebrity romances, but these cringe-worthy proposal stories are anything but enviable.

Seth Rogen and Lauren Miller

Lauren Miller and Seth Rogen | Jesse Grant/Getty Images for AMC

Seth Rogen was so excited to propose to his now-wife, Lauren Miller, he didn’t really think about anything else. And because of that, Miller was completely topless at the time.

“I had already kind of started it. I didn’t picture it like this, and I know she didn’t picture it like this,” Rogen told Conan O’Brien. “I figured the only appropriate thing was to place the ring on her nipple, actually.”

Next: This actor forgot a rather critical step.

Ben Stiller and Christine Taylor

Actor Ben Stiller and actress Christine Taylor

Ben Stiller and Christine Taylor | Lucian Capellaro/Paramount Pictures via Getty Images

Although Ben Stiller and Christine Taylor are no longer together, they shared a beautiful 17 years of marriage together. But Stiller was so nervous on the night he proposed that he forgot the ring.

“I put candles and rose petals leading through her house to the back deck, where I was waiting; it was really cheesy and romantic,” said Stiller. And it was perfect, until he had to run out of the room mid-proposal to grab the ring so that Taylor could (eventually) say yes.

Next: This celebrity super couple’s proposal story isn’t what you might expect.

Will Smith and Jada Pinkett-Smith

Will Smith and Jada Pinkett Smith

Will Smith and Jada Pinkett Smith | Adrian Sanchez-Gonzalez/AFP/Getty Images

Will Smith and Jada Pinkett-Smith are known for being a nontraditional couple, so you might expect them to have a pretty crazy proposal story. In actuality, it was anything but.

“We were just lying there, going to sleep,” Smith told PEOPLE. “I looked over at her, and I said, “Hey, we might be real good married. Wassup? You wanna marry me?’ Unplanned. No ring. Not the classic proposal. She said yes.”

Considering the extraordinary lives these two lead — and the fact that they’ve been married for a very long time — their simple proposal story is actually sweet. However, a non-celebrity couple might not want to go this route.

Next: This bride-to-be chased a FedEx truck for her ring.

Jaime King and Kyle Newman

Jaime King and Kyle Newman | Frazer Harrison/Getty Images

Jaime King knew she was about to get engaged — in fact, she and now-husband Kyle Newman picked out the ring together before planning a very special vacation. But on the day they were set to leave, they somehow missed the delivery. King really wanted the ring to accompany them on the trip, so she chased down the truck.

“I wanted to go on the vacation engaged, with my ring!” King said. “So I got in the car, and I stopped two FedEx trucks, saying, ‘Do you have my ring?’ It was like a scene out of romantic comedy, with me literally chasing down trucks!” They eventually found the ring, and Newman did get down on one knee during their trip.

Next: This proposal didn’t really register.

George Clooney and Amal Clooney

US actor George Clooney and his British-Lebanese lawyer Amal Clooney speak during the 42nd edition of the Cesar Ceremony at the Salle Pleyel in Paris on February 24, 2017.

George Clooney and Amal Clooney | Bertrand Guay/AFP/Getty Images

When George Clooney decided to propose to his now-wife, human rights lawyer Amal Alamuddin, he decided he’d play the song “Why Shouldn’t I?” by Rosemary Clooney, his late aunt. The couple enjoyed a romantic dinner, but just as the song was about to start, Alamuddin decided to get up and wash the dishes.

Clooney eventually called her out of the kitchen and directed her to the box where he was hiding the ring. Her reaction was a simple statement: “It’s a ring.” Perhaps it was because of Clooney’s notorious fear of commitment, but it took the bride-to-be a long time (and several more songs) to realize what was happening. Of course, she said yes, and they’re now the parents of twins.

Next: It seems as if this marriage was doomed from the start.

Amber Heard and Johnny Depp

Amber Heard and Johnny Depp pose together and her hand is on his shoulder.

Amber Heard and Johnny Depp | Michael Kovac/Getty Images for Art of Elysium

Amber Heard did say yes when Johnny Depp proposed to her, but for awhile, it was him who was wearing her engagement ring. The ring he bought her was way too big for her, but it fit him. He ended up getting her a new one.

Next: Talk about cold feet.

Peter Facinelli and Jaimie Alexander

Peter Facinelli and Jaimie Alexander | Randy Shropshire/Getty Images

Peter Facinelli planned the perfect proposal: He arranged for a plane to fly with a banner popping the question at exactly 4:00 when he and Jaimie Alexander were on top of the Empire State Building. But right before the plane was scheduled to fly by, Alexander said she was cold and went inside.

Facinelli chased after her and convinced her to come back out, but it was a cloudy day, and he lost the plane in the horizon. He eventually found it and was able to propose, but the experience was pretty harrowing.

Next: It’s hard to believe anyone would turn down this actor’s proposal.

Matthew McConaughey and Camila Alves

Matthew McConaughey and Camila Alves | Christopher Polk/Getty Images

Matthew McConaughey proposed to Camila Alves on Christmas in front of the whole family … so you can imagine his shock when the first word out of her mouth wasn’t “yes.” After opening the ring (which he’d wrapped eight boxes deep), Alves said she didn’t want to rush the decision. But McConaughey refused to get off his knee until she gave him an answer, and as we all know, the answer was yes.

Next: Somehow, this story isn’t very surprising.

Beth Ostrosky and Howard Stern

Howard Stern and Beth Ostrosky Stern | Larry Busacca/Getty Images for SiriusXM

Howard Stern is known for many things, but being romantic isn’t one of them. When he proposed to Beth Ostrosky, he demanded that she strip naked before he would give her the ring. Somehow, she still accepted the proposal.

Next: Almost every possible thing went wrong for this couple.

Chrissy Teigen and John Legend

Chrissy Teigen and John Legend

Chrissy Teigen and John Legend | Valerie Macon/AFP/Getty Images

John Legend planned to propose to Chrissy Teigen on a trip to the Maldives, but on the way there, things started to fall apart. The couple got into a huge fight on the way to the airport, and then TSA almost ruined the surprise by opening Legend’s carry-on, where he was hiding the ring. When they finally got to the beach, where Legend was hoping to propose, Teigen had horrible cramps.

But when Teigen found the ring hiding in a plate of arugula, none of that mattered. And now they’re happily married with two beautiful children.

Next: This might be the worst proposal story of all.

Megan Fox and Brian Austin Green

Megan Fox and Brian Austin Green

Megan Fox and Brian Austin Green | Kevin Winter /Getty Images

When Brian Austin Green proposed to Megan Fox on the beaches of Hawaii in 2010, she was so excited that she started jumping up and down. And in her excitement, she dropped the ring. And the couple never did find it. Yikes.

Next: Did this actor take lessons from a character on Friends?

Channing Tatum & Jenna Dewan

Actor Channing Tatum (L) and actress Jenna Dewan Tatum attend the grand opening of "Magic Mike Live Las Vegas" at the Hard Rock Hotel & Casino on April 21, 2017 in Las Vegas, Nevada.

Channing Tatum and actress Jenna Dewan | Ethan Miller/Getty Images

Channing Tatum was planning on proposing to Jenna Dewan in 2008, but he didn’t want her to know it. To throw her off, he told her that he didn’t believe in the institution of marriage and that he didn’t think he ever wanted to get married. It worked a little too well. Dewan broke down in tears, prompting Tatum to propose sooner rather than later.

Next:  He could have been asking her to go get takeout.

LL Cool J and Simone Smith

Simone Smith and LL Cool J | Pascal Le Segretain/Getty Images

LL Cool J didn’t put much thought into his proposal to high school sweetheart, Simone Smith. He simply asked her, “Do you wanna do this?” while they were driving around in his Jeep. He didn’t even have a ring. Still, it must have been the right question to ask, because they’ve been married since 1995.

Next: The morning after put a damper on this sweet proposal.

Meghan Trainor and Daryl Sabara

Daryl Sabara and Meghan Trainor | Neilson Barnard/Getty Images

Spy Kids star Daryl Sabara and Meghan Trainor got engaged under a tunnel of Christmas lights surrounded by family and friends. Unfortunately, Trainor also got food poisoning that night, and the next day, she was vomiting everywhere … she even threw up on Sabara. For better or worse, indeed.

Next: These proposal stories will make you swoon.

Not all celebrity proposals are disastrous

Kim Kanye Kardashian-West family

Kanye pulled out all the stops for Kim. | Kim Kardashian via Instagram

As funny and cringe-worthy as these stories are, nothing tops an adorable proposal story. Here are some sweet ways celebs have popped the question:

  • Kanye West proposed to Kim Kardashian by renting out the AT&T Park baseball stadium and hiring a full orchestra, fireworks, and popping the question on the Jumbotron. Kardashian’s family and friends were watching from the bleachers.
  • Ellen Degeneres proposed to Portia de Rossi shortly after de Rossi returned home from a photo shoot with a goldfish. As they admired their new pet, Degeneres asked her lady if she thought the moment was romantic. De Rossi replied that she though all their moments were romantic, at which point Degeneres presented her with a huge diamond ring.
  • Pink was tired of waiting for Carey Hart to propose to her. So she drew up a sign that asked, “Will u marry me?” and held it up for him to see while he was in the middle of a Pro 250 class finals race.

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