John Legend Says TSA Agents Almost Ruined His Surprise Proposal to Chrissy Teigen

Though we all know that John Legend proposed to Chrissy Teigen in the picturesque Maldives in 2011, an airport security blip nearly ruined the “All of Me” singer’s ultra-romantic plan. In an interview with Oprah in 2013, Legend recounted how TSA agents nearly blew the surprise when security officials insisted on searching the box that contained the engagement ring that the groom-to-be worked so hard to conceal from his then-girlfriend.

For Christmas vacation that year, Legend and Teigen had arranged to jet off to the breathtaking island, where the artist intended to get down on one knee, unbeknownst to his partner. While they were going through airport security before boarding their plane, TSA stopped Legend. “[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,” he explained to Oprah. 

Legend started to panic, worrying that his girlfriend would see the engagement ring. “Chrissy was standing right next to me, and I was like, ‘Oh my God, I’ve hid it so well this whole time,’” he recalled of his thought process. “‘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 at the airport.’”

Luckily, Legend’s fears didn’t come to fruition: TSA agents ultimately let him go without opening the ring box, so Teigen didn't see the cushion-cut diamond sparkler in his carry-one bag. Instead, the musician was able to ask his model girlfriend to marry him while they were at dinner one night on their Maldives trip. “This waiter comes out with a silver dome for dessert,” he shared on an episode of FABLife. “So he opens up the dome and a ton of arugula falls out and then I kind of fish in it…And I see the little box and then you know, your heart stops and you get so excited. There was no big grand speech or anything. I think it was just very lovely and sweet.”

According to Zack Stone, a leading diamond expert at fine jewelry company Steven Stone, Teigen’s engagement ring has an estimated value of up to $200,000. The special accessory features a cushion-cut center stone that’s about five or six carats. Plus, the shape of the middle gem has sentimental value since it represents eternal love, per Stone. The diamond is set on a pavé band with a shank that’s lined with small diamonds, adding more brilliance to the bauble.