Shaun White Had Hilarious Failed Proposal Attempts Before Finally Getting Engaged To Nina Dobrev

Asking someone to marry you can be an incredibly daunting task, even if you know their answer before popping the question. There's usually a lot of legwork that goes into a proposal, but things don't always go as planned, even if you happen to be a celebrity. Shaun White's first two attempts at proposing to now-fiancée Nina Dobrev were far less clean than the tricks the former Olympic champion snowboarder effortlessly laid down in the halfpipe.

White planned to propose originally while the couple were on summer vacation. Unfortunately, all his planning crashed and burned when Dobrev injured her knee in an accident while dirt biking. The result was a fracture that required months of rehab and several surgeries to repair.

He later planned on proposing when the two were scheduled to go on a trip to Cape Town, South Africa. It gave him plenty of time to set things up and let her recover from her knee injury. But friends of the couple ended up ruining his potential surprise by asking too many times if they were finally going to get engaged while on the trip. Essentially, they sucked the surprise and special nature right out of it. So White had to think of something else, but that didn't mean it went any smoother.

Shaun White decided to propose in a simple way, at dinner with flowers and a photographer. He spent some time picking the location and planning out the evening, but ran into a problem yet again. Nina Dobrev told White she wasn't feeling well and didn't want to go out at all until they left for the aforementioned trip to Africa. It took just a little white lie to make things come together for the proposal. Shaun White and Nina Dobrev's relationship has been big news for a while, but they finally made it to that next step (after a few tries).

How Shaun White really feels about Nina Dobrev was made clear with the effort that went into his proposal. White got a fake invitation sent to Dobrev that invited her to an exclusive dinner with Vogue editor-in-chief Anna Wintour. He knew she would jump at the chance for that meeting even if he also knew it would be him coming to dinner. Dobrev told Vogue: "He made the invite look so legitimate." When she walked in and saw White and an arch of white roses, she said she "went into shock. I just froze and stared at him." She, of course, said yes to marrying White, and the two eventually announced their engagement online. The truth about their relationship is that they're both very laid back, proving that sometimes simple is better, even when it comes to proposals!