The Cutest Celebrity Engagement Stories to Lift Your Spirits
March 20 is national proposal day. Now, whether or not you decide to recognize that as an actual holiday or just another creation of the Hallmark industrial complex is up to you. Yet at a time when our world seems constantly uncertain, proposals 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?
So it got us thinking: What are some wonderful celebrity engagements to revisit right now? Below, some of our favorite stories, from Prince Harry and Meghan Markle’s intimate engagement over roast chicken to Russell Wilson and Ciara's surprise Seychelles proposal trip.
Serena Williams and Alexis Ohanian
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.
18 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
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
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
Michelle Obama was out to dinner with her eventual husband Barack at their favorite 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.
Katy Perry and Orlando Bloom
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.
Jennifer Lopez and Ben Affleck
Jennifer Lopez indulged our nostalgic “Bennifer” obsession by giving a detailed account of her and Ben Affleck’s engagement in her “On the Jlo” newsletter. “Saturday night while at my favorite place on earth (in the bubble bath), my beautiful love got on one knee and proposed,” she wrote. “It was nothing fancy at all, but it was the most romantic thing I could’ve ever imagined.” Affleck proposed to her with a rare green diamond—which Lopez considers her lucky color.
Prince William and Kate Middleton
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, however, 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
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.
Kourtney Kardashian and Travis Barker
Travis Barker asked Kourtney Kardashian to marry him during a walk on the beach at sunset in Montecito, California. It was no low-key proposal, however. (These are the Kardashians we're talking about, after all.)
Barker covered the sand in hundreds—if not thousands—of red roses arranged in a heart, along with dozens of lit candles. Afterwards, the two families had dinner at the Rosewood Miramar to celebrate. “I’ve never met a better human in my life, like the thoughtfulness, and just everything,” Kardashian later said of her fiancé.
Ciara and Russell Wilson
Russell Wilson surprised Ciara with a trip to the Seychelles for their proposal. In fact, according to her representative at the time, the singer had no idea where she was going until the plane landed on the idyllic African island. The couple stayed at the luxurious North Beach, the same five-star resort where Prince William and Kate Middleton vacationed after their 2011 royal wedding. Wilson proposed to Ciara on their famous “Honeymoon Beach.”
Originally Appeared on Vogue
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