How Shaun White set up a fake dinner with Anna Wintour to propose to Nina Dobrev

Nina Dobrev and Shaun White have announced their engagement following an intimate proposal in New York City.

The couple, who’ve been together since 2019, shared the big news during an interview with Vogue, published on October 30. Speaking to the publication, White explained how he wanted to surprise the actor when popping the question, so he decided to do it during a typically normal week in  October.

He described the weeks he put into planning, involving setting up white roses, candles, and a photographer in a private room at The Golden Swan restaurant in New York City. He also kept the five-carat Lorraine Schwartz engagement ring hidden in different locations around his home where Dobrev couldn’t find it.

White then sent Dobrev a fake invitation from CFDA/Vogue, which asked her to get dinner with the magazine’s Editor-in-Chief, Anna Wintour.

“He made the invite look so legitimate,” Dobrev said.

However, when she opened the door to the restaurant, she discovered that only a photographer and the former snowboarder were there. “I went into shock. I just froze and stared at him,” Dobrev said. Then she went, “no, no, no!” in happy disbelief.

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“I knew she was nervous because when she’s nervous she’ll make jokes. She’s like, ‘So, wait, Anna’s not here?’” White added.

According to the Love Hard star, she doesn’t remember how the proposal went. However, she could recall that when it happened, White “said all the right things.” Once she said yes, the pair were joined by the rest of their friends and family, and they all had champagne to celebrate.

“Eventually we realized – other than the caviar – we hadn’t eaten anything. So we ordered Shake Shack and dumplings to the Golden Swan,” Dobrev said.

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White and Dobrev started dating in 2019 after meeting at an event in Florida. “I actually didn’t know anything about her,” White told People in 2022. However, he then realized she was a celebrity when they got dinner together on another occasion.

“Can we get a photo ... with her?” he recalled one of the waiters at the restaurant asking. “And I was like, ‘What’s happening? What’s going on?’ It was actually really funny.”

However, the couple opted to keep their relationship out of the spotlight for some time, sparking relationship rumors finally in February 2020 when they shared separate Instagram posts from what appeared to be the same location. Two months later, White shared his first-ever post of his then-girlfriend on Instagram.

Speaking to Vogue, White confessed that he initially wanted to propose to Dobrev during their planned vacation for last summer, but the trip was canceled when she got into a biking accident. In May, Dobrev first took to Instagram to reveal she was hospitalized after the accident.

At the time, she shared two photos of herself, with one of them featuring her sitting on an electric bike while the second showed her sitting in a hospital bed in a neck brace with a second brace on her knee.

“How it started vs how it’s going,” she captioned the post.

In June, Dobrev gave an update on her recovery, sharing images from the hospital to reveal she had undergone a successful operation following the accident.

“Thank you to everyone who has been sending kind messages, thoughts, prayers, and good vibes. I have been feeling the support and positive energy. It means more than you will ever know,” she wrote in the caption.