#Love & Sex

The 15 Sweetest Celebrity Marriage Proposal Stories

by Mackensie Graham

The 15 Sweetest Celebrity Marriage Proposal Stories

For many, being asked “Will you marry me?” is a moment they remember forever. While everyone’s knee-drop and ring box story is unique, a celebrity marriage proposal story can truly take the cake when it comes to romance and wow factor. Sure, some celebrities aren’t known for the longest lasting marriages, but the relationships can still be passion-packed. Before the giant star-studded receptions or private, intimate “I do” ceremonies, consider this your embossed invitation to take a peek at how celebs pop the question.





Josh Kelley and Katherine Heigl



Singer-songwriter Kelley was smitten with actress Heigl when he first met her on the set of his 2005 music video, “Only You.” Being a southern gentleman, Kelley had the whole 2006 proposal planned out in meaningful fashion. He rented the Venice Beach bungalow where they first met, complete with wine, cake, and rose petals strewn about. Kelley laughed about maybe adding a couple swear words to the question, but it didn’t matter. Heigl said “yes” and the proposal ended with a romantic stroll down the beach.





Prince William and Kate Middleton



Everyone’s favorite royal couple took the first step toward the infamous 2011 Westminster Abbey wedding ceremony in Kenya in 2010. The Prince asked Kate to be his princess with his mother’s 18-carat sapphire engagement ring. Reportedly, William toted the ring around Africa for three weeks prior to popping the question in the Lewa Wildlife Conservancy in an ultra-private cabin.





Nate Berkus and Jeremiah Brent



Berkus, an American interior designer and American Dream Builders host knows good style, for the home and a proposal! Berkus and Brent, a fellow designer, were on a buying trip for the home decor brand One Kings Lane in April 2013 when Berkus popped the question. The pair took a side trip to summit Machu Picchu, and while walking through a valley past the ancient temples Berkus proposed to Brent. The “yes” resulted in a gorgeous ceremony at the New York Public Library in 2014.





Ben Stiller and Christine Taylor



The actor proposed to his now wife in a comfortable, charming approach. Stiller decorated the actress’ house with scattered rose petals and candles while she was away, then asked for her hand in marriage upon her return. Before the marriage proposal Stiller had to clear a major hurdle: asking Taylor’s dad. Stiller told Life & Style Weekly, “I asked her father for permission before I did it. Christine’s father is an intimidating guy who owns a security company; we’re good friends now, but at the time I was in the basement rec room saying, ‘I really would like to marry your daughter…’ He’s a man of few words but he was very welcoming. I was more nervous asking him than asking her!”





Seal and Heidi Klum



It’s no surprise that the singer of one of the most romantic ’90s songs (“Kiss from a Rose“) ensure that his proposal to supermodel and Project Runway host Klum was simply dreamy. On a vacation in December 2004 to the Candian Rockies, the couple took a helicopter to an igloo built for the engagement. Inside were rose petals, candles, and a comfy bed. Klum told Marie Claire, “There was food and champagne, and then the helicopter left. It was a little scary, too, because you’re so cut off from the world. No trees, nothing – it was hardcore. But I was ecstatic.” The proposal may have been perfect, but unfortunately the couple filed for an amicable divorce in 2012.





Ludacris and Eudoxie Mbouguiengue



The rapper put a new spin on the #milehighclub when he proposed to his then girlfriend, Eudoxie, in a private plane en route to Costa Rica. He projected the question from the plane onto the ground below before getting down on one knee. He told Ellen Degeneres that after the plane looped around she saw the message in the grass, “She burst out into tears and was just extremely happy.” Ludacris shared the news with friends and fans on Instagram, reporting she replied, “Hell yes!”





Matthew McConaughey and Camila Alves



The actor McConaughey wasn’t playing games with Alves’ heart, just being romatic when he wrapped her engagement ring and hid it inside eight different boxes! However, the Brazilian model didn’t consent immediately to the 2011 Christmas Day proposal. McConaughey told Jay Leno, “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.”





Pink and Carey Hart



In classic rock star fashion, Pink had the perfect celebrity marriage proposal. In the summer of 2005 at a motocross finals race in Mammoth, CA, Pink wrote, “Will You Marry Me?” on a board and held it up for her motocross star to see. Hart took another lap around the track to find Pink’s board reading, “I’m serious!” He pulled off the track, let his competitors fly on by and swept the artist up in a winning move. The couple first met in 2001 at the Las Vegas X Games and married in January 2006.





Tori Spelling and Dean McDermott



Reality TV personality McDermott delivered a better gift than Santa ever could when he proposed to Beverly Hills, 90210 actress and reality star Spelling on Christmas Eve in 2005. He created a winter wonderland at a tree farm in Toronto, Canada with a half-mile of twinkling lights leading to a romantic table set for two. McDermott rode up to the Christmas tree-surrounded table and popped the question with not just one ring, but two—a diamond and a sapphire! The couple renewed their marriage vows in 2010.





Kanye West and Kim Kardashian



West spared no expense in the extravagant marriage proposal to Kardashian, solidifying the “Kimye” moniker on Kardashian’s 33rd birthday in 2013. At AT&T Park in San Francisco, West broadcast ‘Pleeease marry meee!!!’ on the scoreboard while a 50-piece orchestra played and Roman candles burned. After Kardashian whispered, “Of course!” West slipped the 15-carat Lorraine Schwartz diamond ring on her finger; friends and family emerged from their hiding spot in the baseball dugouts and the celebration commenced. Of course, the whole affair aired on Keeping Up With The Kardashians.





Tom Cruise and Katie Holmes



Less than three months after they began dating, Cruise proposed to his actress girlfriend in June 2005. Cruise set the scene with a candlelit dinner and an amazing view from the Eiffel Tower Le Jules Verne restaurant. The marriage didn’t last, but it was a sweet proposal.





Sofia Vergara and Joe Manganiello



The actor/director/producer/author planned his celebrity marriage proposal to the Modern Family star weeks in advance. He popped the big question at their suite at the St. Regis Hotel in Princeville, Kauai over Christmas in 2014. Champagne, sweets and a sunset were reportedly involved. The couple first met at the 2012 MTV Movie Awards.





Tara Lipinski and Todd Kapostasy



Fox producer Kapostasy deserves a gold medal for his sweet NYC marriage proposal to Olympic figure skater and commentator Lipinski. As the city and its gorgeous storefronts were dressed up in their December 2015 holiday best, one window was a little out of the ordinary. Lipinski shared on the awwww-worthy tale on Instagram. “Todd knows I love holiday window displays so after a beautiful dinner and on our way for a drink @theplazahotel he said there was window there he thought I’d like to see,” She wrote. “He somehow convinced the hotel to let him take one of their displays over and this painting of him proposing to me in front of my home in California was inside. By the time I turned to him he was on one knee….this is one surprise and Christmas that I will never forget.”





Mariah Carey and Nick Cannon



When you have two amazing artists like Carey and Cannon, one proposal is not enough! Cannon first asked Carey with a Ring Pop candy concealing a gorgeous 17-carat diamond on her NYC apartment rooftop. Then, just a few days later, the pair took a helicopter ride and he proposed yet again while high in the sky. Unfortunately the marriage didn’t last and the pair split in 2014, but Carey got engaged again in January 2016 to businessman James Packer.





Tim McGraw and Faith Hill



The country songbirds were on tour together in the summer of 1996. At the Taste of Country Festival in Colorado, McGraw asked Hill to marry him after her set. He told Today, “It was rainy and stuff and we’d been on tour for a while together. I’d joked around with her about getting married, and so… I looked at her, I grabbed her by the hands before I went onstage. She had already done her show. And I said, ‘I’m really serious. I want you to marry me.'” While McGraw was performing on stage, Hill scribbled her Sharpie answer (“Yes, I’m going to be your wife”), complete with lipstick kisses on his dressing room mirror. Just like that permanent marker, their love seems here to stay—the couple has been married almost 20 years!