Third time’s the charm: Shaun White proposes to Nina Dobrev after scrapping plans twice

Two years into his retirement, Shaun White has pulled off his greatest trick yet.

The three-time Olympic gold medalist on Wednesday announced his engagement to “The Vampire Diaries” alum Nina Dobrev after five years of dating.

“She said YES,” White wrote with an Instagram carousel of photos from the picturesque proposal. He also shared some sweet snapshots on his Instagram story, calling the late October evening the “best night of my life.”

Dobrev also posted an announcement of her own, quipping, “RIP boyfriend, hello fiance” and attaching a few selections from the same batch of engagement photos. In one, she clasps her hands – one diamond-laden, of course – to her mouth in astonishment.

That look of surprise was hard-earned, White told Vogue in an interview published Wednesday.

White’s original plan to propose during the couple’s summer vacation, he told the outlet, was foiled when Dobrev injured her knee in a dirt-biking accident. Later, he scrapped a plan coinciding with their scheduled November trip to Cape Town, South Africa, because Dobrev seemed suspicious – and he was gunning for a true surprise.

So White hatched his final plan, recruiting his publicist to send his now-fiancee a fake invitation to a business dinner with Anna Wintour at the Golden Swan restaurant in New York City. Dobrev accepted.

“He made the invite look so legitimate,” Dobrev told Vogue. When she arrived, she was shocked to find Shaun under an arch of white roses.

“I just froze and stared at him,” she told the outlet, then – like a broken record – she kept saying, “No, no, no!”

Dobrev and White first met during a brief encounter at the 2012 Teen Choice Awards but were formally acquainted several years later at a Florida workshop organized by motivational speaker Tony Robbins. They made their relationship official in 2020.

The two supported each other through the COVID-19 lockdowns, White told People in 2021, with Dobrev keeping the athlete grounded during his final Olympic run in Beijing.

“Nina’s incredible. What an influence on my life,” he said. “Not only does she run her own show, her own world, companies she’s involved in, things she’s producing, all this stuff going on. She holds me to this same high standard which is so wonderful to have in a partner.”

Celebrating White’s birthday in September, Dobrev said there were “too many photos, too many adventures, too much laughter, too many cute moments” to fit into a single post.