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Epic Celebrity Holiday Engagements That Make Us Swoon

The holidays are a time for family, delicious food and gift-giving. Sometimes the gifts are small, but other times they are life-changing and pretty expensive, like a sparkly engagement ring. Celebrities are just like the rest of us — they love a festive proposal. It’s hard not to swoon over celebrity holiday engagements.

Thanks to social media, holiday engagements have been taken up a notch. Now, stars are sharing their often extravagant, over-the-top engagements with the world. Fans are able to get a glimpse at celebs’ special moments, from the exotic locations to the romantic gestures leading up to the official ask and the presentation of the ring.

Love is especially in the air over the holidays, and many celebrities have decided to pop the question during this special time of year. We’ve assembled a roundup of holiday engagements over the years, and the list has some of our Hollywood favorites who have been lucky enough to have an unforgettable holiday moment.

John Legend & Chrissy Teigen

Chrissy Teigen and John Legend’s engagement occurred in 2011, while they were vacationing in the Maldives over Christmas. She shared the story on the Fab Life when they were celebrating their second wedding anniversary.

“I remember we got into a very big fight in the car on the way to the airport because we had opened our presents before,” she shared. “He had only gotten me a cookbook and a Crock-Pot. He said, ‘You just wait.’ Wait for what?”

Well, there was an engagement ring waiting for her halfway around the world once the pair landed and checked into their hotel.

“This waiter comes out with this silver dome. I had really bad cramps, by the way, so I was like, let’s get this over with,” Teigen laughed. “So he opens up the dome and a ton of arugula falls out. I see the little box, and your heart stops… there was no grand speech or anything. It was just lovely and sweet.”

Sofia Vergara & Joe Manganiello

Sofía Vergara and Joe Manganiello are one of the hottest couples in Hollywood. He knew that she was the one long before they ever met. Manganiello even told People magazine that Vergara was his celebrity crush before they began dating.

The proposal took place on Christmas Eve, at sunset, while they were on vacation in Hawaii. If you want to love Manganiello even more, he did it in Spanish with the words “Eres mi todo,” which means “you are my everything.”

While they never released an official engagement photo, take a look at Vergara’s 2014 Christmas Eve snap with her family. That left hand was prominently on display.

Serena Williams & Alexis Ohanian

Serena Williams got engaged to Reddit cofounder Alexis Ohanian over the holidays in 2016 while vacationing in Rome, Italy. Naturally, they took to Reddit to announce the news with a cartoon and a poem written by Serena.

A few months later, Williams shared a photo of the scene where the engagement took place. Ohanian had proposed at the same table that they met, and at the time, Williams didn’t know she was four weeks pregnant.

Tom Brady & Gisele Bündchen

Tom Brady and Gisele Bündchen’s engagement was filled with rumors of a private jet, champagne and roses on Christmas Eve in 2008. Unfortunately, that’s not true. Bündchen cleared the air in her Vogue “73 Questions” segment in 2018.

“When he proposed to me, he made up this whole story [about] how my apartment was flooding, and I ran over to fix the situation,” Bündchen said in the video. “When I got there, the whole apartment had candles and rose petals everywhere, and then he went down on his knees to propose, and I’m like, ‘Get up!’”

She was concerned because the New England Patriots quarterback had just had surgery and had three staph infections.

“I was like ‘What are you doing?’ He’s like, ‘I gotta go on my knees,’ and I’m like, ‘No, no, no! Get up, please,’” she said.

Meghan Trainor & Daryl Sabara

It’s hard to top pop superstar Meghan Trainor’s engagement to actor Daryl Sabara. It was the perfect romantic winter wonderland under red and green twinkling lights. The big moment happened on Trainor’s 24th birthday, just a few days before Christmas in 2017. The magic was all captured by her brother, along with a soundtrack provided by Meghan to “Hopeless Romantic.”

It seems that she knew from the early days of the relationship that Sabara was the one.

“We talked about getting married (by) month one,” Trainor told the Today show. “I was aggressive. I wrote a song called, ‘Marry Me.’”

Gabrielle Union & Dwyane Wade

The always-adorable Gabrielle Union and Dwyane Wade got engaged in 2013, and Wade did it in a very special way just before Christmas.

“It was intimate,” he told ESPN in 2013. “I did it at my house. It was very unexpected, just a regular Saturday. My kids were involved, we asked her to marry all of us. Not just me, it’s a package deal. It was cool.”

Union and Wade tied the knot in 2014 and had their first baby via a surrogate in 2018.

Drew Barrymore & Will Kopelman

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Image: Kevin Winter/NBCUniversal/Getty Images. Kevin Winter/NBCUniversal/Getty Images.

Even though their marriage didn’t last, Drew Barrymore and Will Kopelman spent a snowy Christmas in Sun Valley, Idaho, in 2012. That’s where the couple got engaged.

Barrymore excitedly shared her engagement ring on The Tonight Show with Jay Leno a few months later. She and Kopelman had two girls during their union, Olive and Frankie. They divorced in 2016.

LeAnn Rimes & Eddie Cibrian

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Image: Jason Merritt/Getty Images.

Once their respective divorces were settled, Eddie Cibrian proposed to LeAnn Rimes on Christmas Eve in 2010.

Instagram wasn’t really a big thing eight years ago, so the couple posed for paparazzi shots in Malibu to show off the ring. The news also got a lot of play on the red carpet in 2011 as LeAnn coyly posed with her new hardware. Cibrian and Rimes have been married since 2011.

Kaley Cuoco & Karl Cook

Just after Thanksgiving in 2017, on Kaley Cuoco’s 32nd birthday, equestrian Karl Cook proposed to her. While it looks like they were home and Kaley was casually dressed, it’s her epic reaction that made this engagement video go viral. Cuoco was crying from happiness and was so caught up in the emotional moment, she forgot to give him an important answer.

Karl captioned the video, “This is the best night of my life and I think the video shows it is the best night for kaley as well… if she said yes!!!!”

The couple married on June 30, 2018.

Before you go, click here to see which celebrities have been married the longest. 

Julia Roberts and Danny Moder

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