How 32 Celebrity Couples Got Engaged

Given that celebrities are often creatives—actors, musicians, and the like—they come up with equally creative proposals. And honestly? It helps that they're (usually) pretty wealthy. That means private jets, expensive hotels, and entire rooms full of flowers. For some, it's a recipe for the proposal of their dreams.

Still, for some of the celebrities on the list, proposing was a low-key affair. Sometimes because they're a relatively low-key couple, and other times, well—things go wrong. Without further ado, enjoy this deep dive into celebrity engagements.

Matthew McConaughey and Camila Alves

Technically, this starts as a pre-engagement story, but McConaughey told GQ that Alves gave him an ultimatum. "C’mon, Big Boy, Mr. Easygoing-We’ll-Get-to-It-When-We-Get-to-It. Either (expletive) or get off the pot,’” he recalled. So he popped the question: on Christmas day, with the tiny box wrapped inside seven other larger boxes. A hilarious nesting doll!

John Legend and Chrissy Teigen

The engagement between Legend and Teigen was a sweet moment—in the Maldives, over Christmas, with the ring hidden in a plate of arugula. But on the way there, airport security wanted to inspect the carry-on the ring was hidden in. Legend later recounted, “Chrissy was standing right next to me and I was, like, ‘Oh, my God. I've hid it so well this whole time. Now as we're just about to get to the Maldives she's going to find out I have a ring in this box and it's going to ruin the surprise and I'll have to get on my knees in the airport!'"

Miles and Keleigh Teller

Miles and Keleigh were on vacation in South Africa, at the exact spot they started dating. Next to a rose and note tied to a tree, Miles said, "This was the first day that I asked you to be my girlfriend, and today was the last day you woke up as my girlfriend."

Diane von Furstenberg and Barry Diller

Diller and von Furstenberg had a years-long relationship (and started out dating, then became friends, before becoming romantically involved again). For Diller's 59th birthday, von Furstenburg wasn't sure what to get him—so she suggested a marriage. They wed at the courthouse a week later.

Orlando Bloom and Katy Perry

According to Perry, Bloom proposed during a helicopter ride—but it was a comedy of errors. He'd given her a note to read to divert her attention from the ring reveal. “So I’m reading [the note] but I’m hearing the champagne is broken and the bottle’s everywhere...he’s pulling out this box that’s too big for his coat pocket, rips his coat pocket and his elbow goes into the champagne.” Luckily, he still proposed, she said yes, and they landed on a rooftop with all Perry's family and friends in attendance.

Sofia Vergara and Joe Manganiello

After dating for six months in 2014, Manganiello proposed on Christmas Eve during a trip to Hawaii. “We had this big bay window [that I opened up], and the sun was going down pink over the mountains and over the bay, and I had this ring. I had looked at every ring in the world, and this is the ring that I wanted. I had a whole speech prepared in Spanish. I proposed to her on one knee in Spanish with the sun going down. It was awesome.”

Priyanka Chopra and Nick Jonas

Technically, the second Nick Jonas locked eyes with Priyanka Chopra at a party, he got down on one knee and loudly proclaimed, "You’re real. Where have you been all my life?" But 18 months later, he proposed on midnight a few seconds after her birthday, so that their anniversary would technically occur on a different day.

Shaun White and Nina Dobrev

After five years, White proposed to Dobrev in an amazing way. She wasn't feeling well, so he faked an invite to dinner from Anna Wintour herself to get her out of the house. Then, once they arrived at the Golden Swan in New York, he proposed under an arch of white roses.

Marc Jacobs and Char Defrancesco

How many engagements happen at Chipotle?? This one did! Jacobs coordinated a flash mob set to Prince’s “Kiss" at the chain restaurant. The whole performance was a display of love, and a distraction—at the end, Jacobs got down on one knee and formally proposed.

Seal and Heidi Klum

Seal decided he'd propose to Heidi Klum on a "secluded natural glacier" in Whistler, British Columbia. He'd had an igloo made and proposed inside—and later noted that it was a good thing she said yes. They were in a remote spot, with essentially no one around, so it would have been strange to hang out in an igloo if she'd declined.

Jenna Dewan and Steve Kazee

Imagine: you're at a baby shower with all your friends and family, celebrating your pregnancy with boyfriend Steve Kazee. Then, in a surprise move at the aforementioned shower, Kazee gets down on one knee and makes a romantic speech in front of everyone. It's just darling!

Ciara and Russell Wilson

Imagine playing a game of "travel roulette"! Wilson gave Ciara 30 possible destinations to choose from to guess where they were headed on vacation. Turns out: it was at an exclusive resort in the Seychelles, and Wilson proposed on the island's "Honeymoon Beach."

Tara Lipinski and Todd Kapostasy

Seven months after Lipinski and Kapostasy met, Lipinski explained, "We went for a fabulous dinner and then he said let’s get a drink and I want to show you something. He knows I am obsessed with anything Christmas and how much I love Christmas windows in the city. So he convinced the Plaza hotel to take over a window! Not an easy task. He told me he knew of this special window and as I walked by this window I saw a painting of the two of us inside. He had a big painting made of him proposing to me in front of my home in CA. I was so shocked and by the time I turned to him he was down on one knee."

Eva Longoria and José Bastón

Hilariously, Longoria almost missed her own engagement because she was too busy Snapchatting. She was documenting her Dubai vacation with Bastón, and then turned and discovered the rose petals he'd put out. "I should probably stop Snapchating this," she remembers thinking.

David and Victoria Beckham

As soon as David saw Victoria, he noted to his best friend, "I want to marry that one." But for their actual proposal, he waited until they'd checked into a hotel, then (according to The Mirror) gave her roses, decorated the room with lilies, and ordered room service. The dream!

Meghan Trainor and Daryl Sabara

In 2017, Sabara proposed to Trainor on her 24th birthday, "under a tunnel of beautiful Christmas lights and surprised me with my family and friends" as she later noted on Instagram. The whole thing was (adorably) captured on video, and their palpable joy is infectious.

Simone Biles and Jonathan Owens

One day after Valentine's Day, Owens and Biles shared their engagement, which Biles captioned "THE EASIEST YES." She'd been totally surprised and caught off guard, later telling TODAY, "I thought it might happen this year but definitely not on Valentine's Day...That's why it was such a shock. The way he set up everything was just so seamless."

Ben Platt and Noah Galvin

What a treat when you genuinely surprise your fiancé-to-be! Ben Platt and Noah Galvin were headed to dinner and a show—and Platt rented out the restaurant and decorated it with flowers for the special occasion. Sometime later, Galvin proposed back to Platt, with a similar ring. Platt said yes, naturally.

Idris Elba and Sabrina Dhowre 

Elba said he'd wanted to propose on Valentine's Day, but it conflicted with a screening of his directed movie Yardie. So he decided to propose at the screening. “It was a little spontaneous, if I’m honest,” he told People. “I was at a cast and crew screening and among people I loved. We had all worked so hard for this project so I was like I’m doing it right now, here, today.”

John Stamos and Caitlin McHugh

Lots of engagements are Disney-themed, but Stamos went all out. "He put together some of the most romantic moments from Disney and Pixar animation [in a video],” his rep Lara Spencer said. “And then he ended it with Sebastian from The Little Mermaid saying, ‘Just ask the girl’ to John.”

Samira Wiley and Lauren Morelli

Engagements can be low key! “[Lauren] asked me to sit next to her,” Wiley told Out. “Then she got me up, and we started dancing together, and she pulled a ring from behind the couch. Lauren has been married before, so I wanted her to tell me she was ready, her to be the one to propose. I didn't know she was as ready as she was.”

George and Amal Clooney

A point in favor of the casual engagement: George and Amal were having dinner (George made pasta!), and he asked her to get a candle lighter from a drawer behind her. Spoiler alert—he'd hidden an engagement ring in there, and when she pulled it out he proposed.

Josh Duhamel and Audra Mari

Now this is impressive (and complicated!). Josh Duhamel got some help from a hotel concierge (and the tide) to propose to Mari—by literally getting a bottle to was ashore while they were walking on the beach. Inside was a message, addressed to her, asking her to marry him.

Pink and Carey Hart

Pink literally proposed to Carey Hart while he was in the middle of the 2005 Pro 250 class finals. She held up a pit board reading, "Will You Marry Me?" He continued driving, so she held up another sign: "I'm serious!" He stopped his motorcycle and said yes. Aww!

Neil Patrick Harris and David Burtka

Like some others on this list, Neil Patrick Harris and David Burtka ended up doing a dual proposal. Burtka proposed in 2007 at the street corner where they first met. And Harris proposed in 2008 while they were celebrating Valentine's Day. Romantic synergy!

Serena Williams and Alexis Ohanian

In 2016, Alexis Ohanian proposed to Serena Williams at the exact spot they met. Same hotel in Rome, same table. There was even a plastic rat! If you're unfamiliar, it was a callback to their first interaction together, where Williams and friends tried to get Ohanian to vacate a table they wanted by insinuating there was a rat nearby.

Maksim Chmerkovskiy and Peta Murgatroyd

No biggie, but these two got engaged in front of a live studio audience on Dancing With the Stars. On the dance floor during a live performance of Sway, Chmerkovskiy knelt and told her, "I'm in love with you, and I will be in love with you for the rest of my life."

Ludacris and Eudoxie Bridges

As Ludacris and Eudoxie took off in a private jet, Ludacris gor down on one knee. Simultaneously, "Eudoxie Will You Marry Me?” was displayed in blue lights on the ground in front of them. “She didn’t say yes—she said HELL YES," he wrote on Instagram.

Rebel Wilson and Ramona Agruma

When Wilson and Agruma went official, Wilson posted at the time, "I thought I was searching for a Disney Prince...but maybe what I really needed all this time was a Disney Princess." Thus, when they got engaged at Disneyland, it brought their relationship full circle.

Emmy Rossum and Sam Esmail

Emmy Rossum and Sam Esmail had a tradition where they'd read the New York Times "Modern Love" column to each other. "Then one weekend we didn't read it—I don't remember why exactly—and the following Friday he reminded me that we hadn't. I was actually in kind of a bad mood that day, so I said, 'Oh, well I'll read it eventually.' And he said, 'No, no, no, I think you should read it.' And I said, 'I'm having a back spasm. I'm actually going to take a bath and have a glass of wine, but if you really want to hear it I'll read it to you from the bathtub." As soon as she started to read, she realized: it was about a director falling in love with an actress. "Apparently, he had called Daniel Jones at The New York Times and gotten their paper template and gotten the people there to print out a whole mock section on the bottom half...By the time I finished the story, he was down on a knee in the bathroom, with me in the tub."

Gabrielle Union and Dwyane Wade

Cue the tears! Dwyane Wade planned a secret surprise proposal with his kids Zaire, Zaya, and Xavier. The couple was visited their house remodel when the kids called out to them. "Me and D turn around and they're like, 'OK, now!' And they're holding signs that say, '...Will you marry us?'" Union remembered. She thought it was a joke at first: "So I was like, 'Oh, this is embarrassing! Now they've made signs!'" She turned to Wade, and he was down on one knee.

Michelle and Barack Obama

In one of the best proposal stories of all time, Barack took Michelle out to dinner and then told her he wasn't sold on the whole idea of marriage. They started debating it fiercely, and then a waiter came by with a silver tray. The ring was on the tray, naturally. Michelle noted in her memoir, "He’d riled me up because this was the very last time he would invoke his inane marriage argument, ever again, as long as we both should live."