The Best – and Worst – Celebrity Proposal Stories
It's okay, George, you're in good company
Oh, the marriage proposal.
Some people spend years fantasizing about how it will all go down. The thousands of candles, the white horse, the meteor-sized ring – who isn’t enchanted by the possibilities for the sacred moment?
Even celebrities, like George Clooney and Kanye West, want to get their proposals just right. Their access and wealth mean that they can plan some of the most impressive displays of affection. But sometimes, even they manage to turn the fairytale question into a nightmare.
In honor of National Proposal Day, some of the highlights – and lowlights – of celebrity engagements:
One of the greats: Prince Harry and Meghan Markle
During their first sit-down interview since getting engaged, Markle and Prince Harry divulged details of the royal’s proposal. “It was a cozy night,” Meghan told the BBC. “We were roasting chicken. It was just an amazing surprise. It was so sweet and natural and very romantic. He got down on one knee.”
Harry added: “It was a really nice moment — it was just the two of us. I think I managed to catch her by surprise.”
One of the mishaps: Aidy Bryant and Conner O’Malley
Saturday Night Live star Aidy Bryant told host Seth Meyers about how longtime boyfriend Conner O’Malley proposed to her, noting that she returned home from work at SNL one night in October 2016 to find her and O’Malley’s dog wearing a bowtie. “I was like, ‘My dog doesn’t wear a bowtie! Where is he going tonight?’ Basically, the second I shut the door, a man — who I discovered was Conner — frantically came around the corner and was just like, ‘Will you marry me?!’ No box. No ‘I love you.’ ”
She continued: “Just a man in full terror standing very far from a dog in a bowtie, just holding a loose ring going, ‘Will you marry me?’ I was like, ‘What?’ I truly couldn’t comprehend what was happening, and I kept saying, ‘Is this a joke? Are you doing a joke?’ And then I said, ‘Of course I’ll marry you. I love you.’ And it was really nice.”
One of the greats: Kanye and Kim Kardashian West
Ye brought it when it came time to pop The Question.
The rapper surprised Kim by renting out AT&T Park in San Francisco on her 33rd birthday. A full orchestra and a pyrotechnic display greeted them when they arrived at the stadium, and a message from Kanye – “PLEEEASE MARRY MEEE!!!” – lit up the jumbotron as he fell to his knee.
And the surprises weren’t even over: After the ask, Kim’s family came out from hiding in the dugouts to celebrate.
One of the mishaps: George and Amal Clooney
They might be one of the hottest couples on the planet right now, however, the pair didn’t really stick to the script when it came to their actual engagement.
The actor hid the ring in a box to surprise her with during a home-cooked dinner. But the big reveal got quite an underwhelming response.
“I’ve got it all set up, timed out and the song is coming and she gets up to go wash the dishes, which she’s never done,” Clooney recounted for Ellen DeGeneres on her show. “And I’m like, ‘What are you doing?’ and she comes back in. And finally I said, ‘Ya know, I blew out the candle,’ and I said, ‘I think the lighter’s in the box behind you.’ And she reaches around and she pulls out the box and I’ve got just the ring sitting in there and she pulls it out and she looks at it and she’s like, ‘It’s a ring’ – like as if somebody had left it there some other time.”
Amal and George eventually got on the same page after he dropped down on one knee, but it took some time. “We now know because there was a playlist so we know how long it actually took, and it’s like 25 minutes,” Clooney said about getting a response from his now-wife. “And finally I literally said ‘Look, I hope the answer is yes but I need an answer because I’m 52 and I could throw out my hip pretty soon if I don’t get an answer.’ ”
One of the greats: Maksim Chmerkovskiy and Peta Murgatroyd
Of course the Dancing with the Stars pros’ engagement story involved dance.
Chmerkovskiy got down on one knee on the dance floor during a performance of the pair’s show Sway in Miami, as the audience and other dancers looked on.
“I’m in love with you, and I will be in love with you for the rest of my life,” he said.
In a statement to PEOPLE, Murgatroyd said she definitely approved of the (literally) show-stopping proposal: “Maks’ romantic proposal is something I will cherish for the rest of my life.”
One of the greats: Joe Manganiello and Sofia Vergara
We somehow love the perfect male specimen even more after hearing about his adorable proposal, which he delivered in Princeville, Kauai. The star worked hard to drop the “M” word in his lady’s native language.
“I had a big speech in Spanish, and that’s what I was nervous about,” he admitted on Live! with Kelly and Michael. “The last thing you want to do is like mess up the Spanish on the proposal to the Colombian woman.”
The actor said he included “Eres mi todo” (which means “you are my everything” in English) in his speech. Cue our hearts exploding.
“You only get one chance to do it, and if you’re gonna do it, you gotta do it right, so there’s a lot of planning that goes into it,” Manganiello said.
One of the mishaps: Matthew McConaughey and Camila Alves
The Oscar winner decided to propose to Alves in front of the whole family while opening Christmas presents. Unfortunately, Alves didn’t feel the need to rush to a decision just because the fam was looking on.
“At Christmas time, we go around our family and everyone takes turns opening presents. So I had wrapped the engagement ring in about eight different boxes deep, so she would keep opening boxes to get with it,” McConaughey revealed on The Tonight Show with Jay Leno in 2012. “We finally got to her, and I’m calling my family over. She gets to it, she opens it up, her eyes go wide. I take a knee and I ask her, ‘Will you marry me and take my name?’ ”
And then things got a bit awkward: “The first words out of her mouth were not ‘yes.’ I’m not gonna say what it was. But I did say, ‘Look, I’m down on a knee. I’ll stay here awhile. I will outlast you.’ And I did! She conceded.”
McConaughey’s other half doesn’t seem to have any regrets about her answer; the pair has now been happily married for almost four years.
In fact, Cannon proposed to the star not once, but twice.
For the first go, Cannon took Carey to the rooftop of her Manhattan apartment. There, he presented her with a diamond hidden inside of a – wait for it – candy ring pop.
Carey told ELLE that she got to relive the big moment a few days later when he proposed again. “He sort of kidnapped me and took me on a helicopter ride,” she said. “Then he re-proposed.”
One of the mishaps: Seth Rogen and Lauren Miller
The actor was so tense after picking up the ring that he nixed his intricate plans and went for an impromptu – and hilariously NSFW – proposal.
“I had all these elaborate plans you know and when I got the ring it was so nerve-racking having this ring like literally I felt like someone had given me a truckload of heroin to hold on to,” Rogen joked on Conan. “I was just so nervous when I got it. 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.’ ”
“So I had all these plans but like the day I got the ring, literally the second I got it, I walked right upstairs to where she was to propose to her,” he continued.
“But she was in our closet changing and she was literally only in her underwear and her boobs were out. And I had already kind of started, I was like ‘Oh man, her boobs are out, that’s not part of the plan. I didn’t picture it like this and I know she didn’t picture it like this.’ No little girl is like ‘It’ll happen in a closet with my titties out.’
“I figured the only appropriate thing was to place the ring on her nipple,” he added. And scene.
One of the greats: Ludacris and Eudoxie Mbouguiengue
Despite the risk of involving aviation in your proposal plans, Ludacris’ plane scheme went off without a hitch (get it, hitch?).
“I look at myself as a pretty romantic guy. I’m a creative guy. You gotta be creative, you gotta be different. And these things stick with women for the rest of their lives so I had to go above and beyond,” the rapper said about his engagement on The Ellen DeGeneres Show.
Luda had “Will you marry me” written in giant letters on the grass where it could be seen as the couple flew on a private plane in Costa Rica.
“Of course she burst out into tears and was just extremely happy. So it was a pretty original idea,” he added.
One of the mishaps: Will and Jada Pinkett Smith
According to the actor, the Smiths actually appreciate that their nontraditional proposal was a simple affair, but it’s safe to say it wasn’t your typical engagement event.
“We were just lying there, going to sleep,” Smith recalled to PEOPLE in 2005. “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.”
“It’s really weird when you live the kind of lifestyle that we live: Simplicity becomes the jewel,” he added.
One of the greats: Russell Brand and Katy Perry
It’s another marriage that’s history, but had a beginning so cute we can’t forget it.
Russell made the ask during a romantic getaway to Jaipur, India, where he arranged a candlelit garden dinner. At the stroke of midnight, the duo was treated to a New Year’s fireworks celebration as they sat on top of an elephant. Then, Brand asked Perry if he could become her husband.