Chrissy Teigen and John Legend's Relationship Timeline

Chrissy Teigen and John Legend are one of the coolest couples in Hollywood. After being together for nearly two decades, they've become the blueprint for a successful celebrity relationship, balancing fame with family and maintaining a good sense of humor through all of life's ups and downs.

Each year, the pair continues to set the bar for relationship goals — whether they're showcasing their love for each other in a very public way (it helps that one half of the couple is a singer-songwriter) or simply spending time together as a family with their four children, Luna, Miles, Esti, and Wren, at their impeccably-designed Los Angeles home.

For every major milestone and adorable moment in between, take a look back at Chrissy and John's adorable love story. 

September 2006: Chrissy Teigen and John Legend meet. 

Chrissy and John first met on the set of his music video for the singer's single "Stereo." Teigen, who was a budding model at the time, starred as Legend’s love interest in the video and later revealed that there was a spark between them off-screen. “We did the music video. We were together for like 12 hours,” she told Wendy Williams during an interview in 2014. “We spent the entire day together, me in my underwear and him in a full suit, and I went to go say goodbye to him, to his hotel, and we didn’t ever say goodbye that night.”

But they didn't immediately start dating. "I left him by himself for a while," Teigen previously revealed to Cosmopolitan. "The worst thing you can do is try to lock someone like that down early on, then have them think, 'There's so much more out there.' I played it cool for a long time. Never once did I ask, 'What are we?'"

2007: Chrissy Teigen and John Legend break up for a day.

Months after officially becoming a couple, Chrissy joined John on tour, and while on the road, they had a brief breakup that only lasted a day.

“I was on tour with him, and he’d gotten sick,” Teigen later revealed to Cosmo. “He was feeling really bummed and stressed out. He was like, ‘I can’t be in a relationship right now.’ That lasted for one day. Literally, a day. I knew it came from a place other than us not working. It was the stress of him having to maybe cancel a show, and he had never been in a real relationship—or so he says now. I always joke, ‘Remember when you tried to break up with me?’ He’s like, ‘Yes, sorry. Big mistake.'”

February 2008: Chrissy Teigen and John Legend make their red carpet debut at the Grammys.

Legend and Teigen made their red carpet debut at the 2008 Grammy Awards — and like most throwback photos, the cookbook author looks back and laughs: "Grammys 2008. 10 years ago. This tan!!! Lmao," she captioned a snap of the couple from the award show.

December 2011: Chrissy Teigen and John Legend are engaged.

John proposed to Chrissy during their holiday trip to the Maldives, but things didn't go exactly according to plan.

“[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,” Legend said during a 2013 appearance on Oprah’s Next Chapter. “And 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.'”

Luckily, he didn't have to propose in the security line at the airport.

Chrissy chimed in, “We get to the Maldives, and he had planned this beautiful Christmas. He knows how much I love Christmas…And this waiter comes out with a silver dome for dessert…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," adding: "There was no big grand speech or anything. I think it was just very lovely and sweet.”

August 2013: John Legend releases his song "All of Me" about Chrissy Teigen.

In perhaps the greatest romantic grand gesture of all time, Legend released his song "All of Me" in honor of Teigen. "The first line of it is, 'What would I do without your smart mouth,' so if that's not about me, I don't know what is," Chrissy told the Huffington Post at the time. "I did cry when I heard it. I'm emotional, but like I don't really cry at things like that, so yeah, it was beautiful. And live, it's pretty unreal." She later starred in the single's music video, which included footage from their Lake Como wedding at the end.

September 2013: Chrissy Teigen and John Legend are married.

On September 10, 2013, Chrissy and John got married at the courthouse in New York City (model Irina Shayk was their witness), days before their wedding in Lake Como, Italy, on the 14th. At their second ceremony, Legend serenaded Teigen, who was clad in multiple Vera Wang gowns, with the song "All of Me."

December 2015: Chrissy Teigen and John Legend announce they are expecting their first child.

Teigen revealed that she and Legend were going to be first-time parents after having difficulty conceiving. She shared the happy news alongside a sweet note and photo on Instagram.

"John and I are so happy to announce that we are pregnant," Teigen wrote in the caption. "As many of you know, we've been trying to have a baby for a while now. It hasn't been easy, but we kept trying because we can't wait to bring our first child into the world and grow our family. We're so excited that it's finally happening. Thank you for all your love and well wishes. I look forward to all the belly-touching! Xx."

April 2016: Chrissy Teigen and John Legend welcome their first child. 

Chrissy and John's first child, a daughter named Luna Simone Stephens, was born on April 14, 2016. She later shared a photo of the couple's newborn baby on Instagram, revealing that her nickname was "Lulu."

November 2017: Chrissy Teigen is pregnant with her and John Legend's second child.

Chrissy revealed that she and John were expecting their second child with her signature sense of humor. "It's John's," Teigen wrote alongside the couple's pregnancy announcement video on Instagram.

May 2018: Chrissy Teigen and John Legend's second child is born. 

Chrissy and John welcome a baby boy, Miles Theodore Stephens, on May 16, 2018.

April 2019: Chrissy Teigen and John Legend get matching tattoos.

The couple got matching tattoos in honor of their growing family. In cursive handwriting, Teigen and Legend had each other's names, plus the names of their kids, Luna and Miles, inked on the inside of their arms.

September 2020: Chrissy Teigen and John Legend suffer a pregnancy loss. 

A month after revealing she was pregnant with her and Legend's third child in the singer's "Wild" music video, Teigen suffered a miscarriage at 20 weeks, sharing the news in a heartbreaking Instagram post.

"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," Teigen captioned a slideshow of candid black-and-white photos from the hospital.

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."

August 2022: Chrissy Teigen is pregnant again.

Nearly two years after her devastating pregnancy loss, Teigen was happy to share with fans that she and Legend were expecting another baby following IVF treatments.

"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," she captioned a set of images showing off her baby bump in a pair of see-through Gucci underwear. Chrissy added, "Every appointment, I’ve said to myself, 'ok, if it’s healthy today, I’ll announce,' but then I breathe a sigh of relief to hear a heartbeat and decide I’m just too nervous still. I don’t think I’ll ever walk out of an appointment with more excitement than nerves, but so far, everything is perfect and beautiful, and I’m feeling hopeful and amazing."

October 2022: John Legend admitted he wasn't a great partner to Chrissy Teigen when they first started dating. 

John wasn't afraid to own up to his past mistakes in his relationship with Chrissy during an appearance on Jay Shetty's podcast On Purpose.

"I was more selfish then," Legend shared. “I wasn't a great partner at the beginning of our relationship, even though I was very into her and very excited to be with her. I was still selfish. I was in my mid-20s, still not ready to fully be the committed partner that I am now."

Admitting that it took time for him to become a better partner to Teigen, Legend continued: “When you stop being so selfish when you think about not only the joy you get from a situation and the pleasure you get from it but also think about your responsibility and your commitment in that situation. You just grow, and you mature. Part of it is it's just a matter of time. You need time to become that person you want to be.”

January 2023: Chrissy Teigen and John Legend welcome their rainbow baby.

Chrissy and John officially became parents of three on January 13, 2023, when they welcomed daughter Esti Maxine Stephens.

"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," she captioned a sweet photo of the couple's two older children holding their baby sister. "Thank you for all the love and well wishes - we feel it all! X

June 2023: Chrissy Teigen and John Legend secretly welcome a baby via surrogate.

In a surprise baby reveal on June 19, 2023, Teigen and Legend revealed that their family just gained a new member. Months after Teigen was already pregnant with Esti, her surrogate Alexandra also became pregnant with the couple's baby boy, Wren Alexander Stephens.

"As we crept toward the safe zone of my own pregnancy, we were overjoyed to learn Alexandra had become pregnant with a little boy. Our little boy," Chrissy explained in a post on Instagram. "We ate hot pot to celebrate, watched Vanderpump Rules with our growing bellies, our families blending into one for the past year." She added, "Just minutes before midnight on June 19th, I got to witness the most beautiful woman, my friend, our surrogate, give birth amidst a bit of chaos, but with strength and pure joy and love."

Teigen went on to reveal that she and Legend even paid tribute to Alexandra with their son's middle name. "We want to say thank you for this incredible gift you have given us, Alexandra," she wrote. "And we are so happy to tell the world he is here, with a name forever connected to you, Wren Alexander Stephens."