Chrissy Teigen and John Legend's Biggest Relationship Milestones

The couple dated for nearly two years before they made their first joint red carpet appearance at the Grammys in February 2008. Reflecting on the special event, Teigen shared a picture on Instagram in 2018, writing, "Grammys 2008. 10 years ago. This tan!!! Lmao."

After dating for five years, Legend decided to take his relationship with Teigen to the next level and propose during a Christmastime vacation 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.

On Sept. 14, 2013, the couple made their union official in a ceremony in Lake Como, Italy, but days prior, they actually got legally married in a New York City courthouse. In an interview with E! News, Teigen revealed, "We actually got married after going to a couple Fashion Week shows at Vera Wang, ironically who actually did my dress, but we got married at the courthouse right after," she told the outlet. "We are dumb and didn't realize that our Italian wedding would not be recognized unless we had a real ceremony in New York City. So Irina Shayk was our witness — the most beautiful woman on earth!"

Teigen revealed that she and Legend were expecting their second child in November 2017 in a sweet Instagram video. The video shows Teigen pointing to her belly and Luna saying there's a baby inside it while Legend can be heard gleefully laughing in the background.

The couple's second child, Miles, was born on May 16, 2018. In an Instagram announcement, Teigen wrote, "Hello, world! This is Miles Theodore Stephens. We are drowning in his little peeps and nuzzles. Our household feels overwhelmed with love. Thank you for all your well wishes!"

In September 2020, Teigen and Legend had a pregnancy loss while Teigen was pregnant with their third child. In a heartbreaking Instagram post, Teigen shared emotional pictures from her hospital, writing, "We are shocked and in the kind of deep pain you only hear about, the kind of pain we've never felt before. We were never able to stop the bleeding and give our baby the fluids he needed, despite bags and bags of blood transfusions. It just wasn't enough."

She continued, "We never decide on our babies' names until the last possible moment after they're born, just before we leave the hospital. But we, for some reason, had started to call this little guy in my belly Jack. So he will always be Jack to us. Jack worked so hard to be a part of our little family, and he will be, forever."

Two years after their pregnancy loss, Teigen announced on Instagram that she and Legend were expecting again, writing, "the last few years have been a blur of emotions to say the least, but joy has filled our home and hearts again. 1 billion shots later (in the leg lately, as u can see!) we have another on the way."

On Jan. 13 2023, Esti Maxine Stephens was born. Teigen shared a picture of her baby girl on Instagram with Luna and Miles holding her, writing, "She's here! Esti Maxine Stephens - the house is bustling, and our family could not be happier 💕 Daddy sheds nightly tears of joy seeing Luna and Miles so full of love, and I am learning you still need diapers with a c-section!? We are in bliss."

In September 2023, on the 10th anniversary of their wedding, Teigen and Legend renewed their vows. The pair returned to their original wedding destination in Lake Como, Italy, for the special occasion. A source close to the couple told People, "It was very romantic . . . They arrived by boat . . . It was breathtaking to see them still so happy together."

Speaking to People in October 2023, Legend said their "speeches had everybody in tears." He added, "Chrissy spoke first, and the whole room was just weeping. And then I was able to speak and sing to her."

Legend revealed that he brought out their four kids to sing a rendition of his song "It Don't Have to Change." "It's a song that we sing together as a Stephens family, and that was pretty magical," he noted.