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Before he finally proposed to his fiancée, Nina Dobrev, the Olympic gold medalist had two unsuccessful attempts.
What went wrong with the first two attempts, then? In an article published on October 30, Shaun told Vogue that he had originally intended to pop the question to the Vampire Diaries star during their summer break this year, but the plan was derailed when she suffered a surprise fracture to her knee in a May biking accident. The injury ultimately required months of rehabilitation and surgery, which Nina later described as "success."
However, Shaun encountered additional challenges when attempting to put his five-carat Lorraine Schwartz ring on her finger. During a November trip to Cape Town, South Africa, the 38-year-old also came up with the idea to ask for her hand in marriage. However, friends of the couple spoiled the surprise by incessantly asking if that was the planned date.
The former professional snowboarder ultimately made the decision to keep things simple by arranging a small dinner at The Golden Swan Restaurant in New York, complete with flowers and a photographer. Additionally, he refused to change the date when Nina, 35, informed him that she wasn't feeling well before the big night, choosing instead to have his publicist send her a phony invitation to an exclusive Vogue dinner with editor-in-chief Anna Wintour that he knew she wouldn't be able to pass up.
Nina told Vogue that "he made the invite look so legitimate."
When she finally reached the spot, she was shocked to see that Shaun was the only person behind the door. Nina went on, "I went into shock." "I just froze and stared at him."
Naturally, the Degrassi alumnus gave a resounding yes in response to his major query. A few days later, the couple—who initially revealed their relationship while under quarantine together during the COVID-19 lockdown in 2020—publicly celebrated the momentous occasion. Nina wrote, "RIP boyfriend, hello fiancé," in an Instagram post on October 30.
