The Cutest Celebrity Engagement Stories To Lift Your Spirits

NEW YORK NY  MAY 07 Amal Clooney  and George Clooney attend the Heavenly Bodies Fashion  The Catholic Imagination...
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We’re in the thick of engagement season – or the period between Thanksgiving and Valentine’s Day which traditionally has the highest rate of proposals. At a time when our world seems constantly uncertain, they can be a heartwarming distraction from a darker reality… especially when the engagement is between two famous faces. C’mon, who doesn't like to indulge in a little celebrity love story now and then?

Read more: The Engagement Ring Trends You’ll See Everywhere In 2022

So, it got us thinking – what are some wonderful celebrity engagements to revisit right now? Below, our favourite stories, from Prince Harry and Meghan Markle’s intimate engagement over roast chicken to Kim and Kanye West’s over-the-top stadium proposal.

Serena Williams and Alexis Ohanian

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Serena Williams and Alexis Ohanian first met at the Cavalieri Hotel in Rome, after the Reddit co-founder sat down at a breakfast table near hers. Originally put off by his close proximity, one of Williams’s friends joked that there was a rat by his table – to which Ohanian replied that he was from Brooklyn, so he was used to rats.

Eighteen months later, he was ready to propose in fantastical style. “I came home one day to find my bags already packed for me, and I had absolutely no idea where I was going until I got on the flight,” Serena told Vogue. “Alexis flew me out to Rome, back to the exact table where we’d met. We were both really nervous but also excited to take this huge step. It was such a beautiful moment.” Oh, and on the tabletop? A plastic rat.

Prince Harry and Meghan Markle

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Royal life comes with a lot of pomp and circumstance – which is why, perhaps, Harry chose a simple yet intimate way to propose to Meghan Markle. During a night in, when the couple was cooking a roast chicken, Harry pulled out the ring. “It was just an amazing surprise,” Markle recalled in an interview. “It was so sweet and natural and very romantic; he got on one knee.” In fact, she was so overwhelmed and overjoyed that, according to Harry, “she didn’t even let me finish.”

George and Amal Clooney

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Like Prince Harry, George Clooney also planned a quiet engagement. First, he made pasta for the two to enjoy. “Then over champagne, after dinner, I told her there was a lighter to light the candle in the drawer, and she reached back and pulled out a ring,” he told The Hollywood Reporter. Amal was so shocked that it took her 20 minutes to respond.

Michelle and Barack Obama

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Michelle Obama was out to dinner with her eventual husband (and president) Barack at their favourite Chicago restaurant, when Barack brought up that he wasn’t too sold on the idea of marriage. “Instantly, I felt the blood rise in my cheeks. It was like pushing a button in me – the kind of big blinking red button you might find in some sort of nuclear facility surrounded by warnings signs and evacuation maps. Really? We were going to do this now?” Michelle wrote in her best-selling memoir, Becoming. The couple then began to debate “attorney-style” over the matter. Come dessert, a waiter came over with a silver tray. When he lifted up the lid, it revealed a ring box. Barack, it turns out, had just been playfully baiting his successful lawyer wife-to-be the whole time. “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,” Michelle concluded. 

Kim Kardashian and Kanye West

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Kanye West is always dreaming big – and that was particularly true when it came to his proposal. The rapper proposed to Kardashian in 2013 by renting out the entirety of San Francisco’s AT&T Park. While the Chicago Symphony played, “PLEEEASE MARRY MEEE!!!” flashed upon the Jumbotron. Although they are no longer together, his over-the-top gesture still tops the list of celebrity engagements.

Katy Perry and Orlando Bloom

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When it came time to pop the question to Katy Perry, Orlando Bloom also went over the top. Perry told the story on Jimmy Kimmel Live: “We went to dinner. I thought we were going to go see some art after dinner, but we pulled up to a helicopter,” she said. “He asked me to marry him in a helicopter.” Afterwards, they landed on a rooftop full of their family and friends.

Gisele Bündchen and Tom Brady

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In her “73 Questions” video with Vogue, the Brazilian supermodel shared how the famed football quarterback asked her to marry him. “When he proposed to me, he made up this whole story about how my apartment was flooding. I ran over there to try to fix the situation. When I got there, the whole apartment had candles and rose petals everywhere,” she said. Slight problem: Brady was recovering from an injury, so when he got down on his knee, Bündchen begged him not to. “I was like – get up!” Because he just had surgery! She said yes, and the couple has been married for almost 13 years. 

Prince William and Kate Middleton

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Prince William admitted that he carried around Kate Middleton’s now-iconic engagement ring for about three weeks before popping the question at the foothills of Mount Kenya. “I literally would not let it go, everywhere I went,” he later said in an interview. “I was keeping hold of it because I knew this thing, if it disappeared, I would be in a lot of trouble.”

He did manage to hang onto it, and one night on their African adventure, the time was right.  “He’s a true romantic,” Middleton said. “It was out there in a very quiet lodge.”

Gabrielle Union and Dwyane Wade

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Dwyane Wade and Gabrielle Union’s proposal was a family affair. Wade had his two children hold up signs that read “Will you marry us?’” Union said yes – to him first, and then to their kids.