After dating for five years, Legend decided to take his relationship with Teigen to the next level and propose during a Christmas holiday in the Maldives in December 2011. However, the entire surprise was nearly ruined by airport security. "[The ring] was in my carry-on bag going through airport security, and security wanted to look through my bag, and they wanted to look in that particular box," the musician shared in a 2013 interview on "Oprah's Next Chapter". "Chrissy was standing right next to me, and I was like, 'Oh, my God. I've hidden it so well this whole time. Now as we're just about to get to the Maldives, she's going to find out I have a ring in this box, and it's going to ruin the surprise, and I'll have to get on my knees in the airport.'"
Thankfully, security decided to not check the mysterious box, and Legend was able to propose the way he'd planned once they arrived in the Maldives.