Shaun White Tried to Propose to Nina Dobrev Twice Before Engagement

Shaun White didn't stick the landing on his first two proposal ideas. 

The Olympic gold medalist had two failed plans to pop the question to his fiancée Nina Dobrev before finally getting down on one knee. 

So, what went wrong those first two go-arounds? Shaun revealed to Vogue in a story published Oct. 30 that he initially wanted to propose to the Vampire Diaries alum during their summer vacation this year, but the idea was thwarted after she unexpectedly fractured her knee during a biking accident in May. Nina eventually underwent months of rehabilitation and surgery over the injury, which she later shared were a "success."

But that's not the only obstacle Shaun faced while trying to put his five-carat Lorraine Schwartz ring on her finger. The 38-year-old also had the idea to ask for her hand during a November trip to Cape Town, South Africa—until friends of the couple ruined the surprise by repeatedly asking if that's when it was going to happen.

In the end, the former pro snowboarder decided to keep the moment simple, setting up an intimate dinner with flowers and a photographer at The Golden Swan Restaurant in New York. And when Nina, 35, told him she wasn't feeling well ahead of the big night, he refused to move the date, instead opting to have his publicist send her a fake invitation for an exclusive Vogue dinner with editor-in-chief Anna Wintour that he knew she wouldn't be able to pass up. 

As Nina recalled to Vogue, "He made the invite look so legitimate."

To her surprise, only Shaun was behind the door when she finally arrived at the location. “I went into shock," Nina continued. "I just froze and stared at him."

Of course, the Degrassi alum's response to his big question wound up being a resounding yes. And a few days later, the couple—who first went public with their relationship while quarantining together during 2020's COVID-19 lockdown—publicly announced the exciting milestone, with Nina writing in an Oct. 30 Instagram post, "RIP Boyfriend, hello fiancé.”

To relive more sweet moments in Nina and Shaun's love story, keep reading. 

Dobrev and White hit it off after they partied together with friends, including her Vampire Diaries co-stars Kayla Ewell and Candice Accola King, at the opening of the Bellagio Resort & Casino's new supper club The Mayfair in Las Vegas on New Year's Eve.

A year later, amid the coronavirus pandemic, Dobrev would share this photo of her and White at the bash, as well as a video of him lifting her up Dirty Dancing-style only to have them both topple into the snow. She wrote, "How we thought 2020 would go...how it actually went."

Dobrev and White spark romance rumors after they are spotted riding bikes together in Malibu, Calif. A source tells E! News that the two began to "ease into a relationship" after spending New Year's Eve together, adding that things "really accelerated" between the two after the coronavirus pandemic broke out.

"After spending weeks together during quarantine," the source says, "Nina and Shaun have made it clear to their friends that they are a serious couple."

The two make their relationship Instagram official when both share a photo of the actress trimming White's red hair. Most hair salons closed due to COVID-19 restrictions. Under her post, Dobrev writes, "Adding to resume: hairdresser."

Dobrev and White celebrate Thanksgiving with his family, as seen in photos he posts on Instagram.

Judging from their Instagrams, Dobrev and White vacationed together in the Zion National Park area in Utah twice in 2020, in May and in December.

The two spend the holidays together in December 2020.

Just before New Year's Eve, another source tells E! News that the two "are genuinely so in love."

"They openly talk about their future together," the insider continued. "They're just super happy, and things are going really well with them."

Dobrev celebrated a "redo" of her 31st birthday on her 32rd and White paid tribute to her with photos of the two sporting these looks.

Alonside pal Adam DeVine, the couple dressed up as characters from The Queen's Gambit for Halloween with White going as as the iconic Beth Harmon and Dobrev channelling U.S. chess champion, Benny Watts.

Dobrev hit the slopes with her pro snowboarder love at Copper Mountain in Colorado.

After White finished fourth in the Men's Snowboard Halfpipe at the 2022 Olympics and officially retired from competing, Dobrev expressed how proud she was of him.

"The end of one chapter, means the beginning of an exciting new one with endless possibilities," she wrote in part of an Instagram post. "You will forever be the G.O.A.T. of snowboarding. Not to mention you are also the G.(B).O.A.T. = Greatest Boyfriend Of All Time."

The couple finally went red carpet official at the Top Gun: Maverick film premiere in London.

Alongside her tux-clad boyfriend, Dobrev sizzled in a red Monot gown at the 28th annual amfAR Gala during the 75th Cannes Film Festival.

The pair watched the qualifying for the F1 Grand Prix of Monaco ahead of the big race. For the occasion, Dobrev looked wore a chic, chalk-colored suit by Smythe.

The two turned up the heat while vacationing in the Maldives.

"I really picked a winner [ and he really picked a booger ]," Dobrev wrote in an Instagram tribute for White's 36th birthday. "Happy belated Birthday you weirdo. My weirdo. @shaunwhite."

What did White really think of Dobrev's cheerleading scene from Degrassi: The Next Generation? The athlete gave his reaction on TikTok and proved once again they're always on each other's squads.

The duo celebrated the holidays with a family trip to Mexico.

"What planet are you from and will you take me with you?!" White wrote on Instagram for Dobrev's 34th birthday during their trip to Antarctica. "Thanks for making life incredible! Happy birthday my love."

"Life is a roller coaster with you," the actress wrote on Valentine's Day 2023. "It goes from serious to baby birding in seconds … thank you for always making me smile. happy valentine’s day @shaunwhite."

"Life with you has been my greatest adventure!!" White wrote on Instagram for Dobrev's 35th birthday. "Happy birthday my love!!"

The duo looked so sharp at the 2024 Vanity Fair Oscar Party they deserve their own trophy.

The two celebrated the Fourth of July with several celebrity friends, including Miles Teller and Keleigh Teller and Usher.

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