George and Amal Clooney have a lot to celebrate. On September 27, the couple will welcome their fifth anniversary, marking another milestone of their private romance. Clooney, who was once dubbed Hollywood’s “lifelong Bachelor,” fell in love with human rights lawyer Amal Alamuddin, and their whirlwind romance captivated the world.
In 2014, the couple wed in a lavish ceremony in Venice, Italy. Since then, they’ve dedicated their lives to everything from human rights advocacy work and parenthood, all while maintaining one of the most reserved (but admired) Hollywood relationships.
In honor of their anniversary, we’re looking back on the couple’s sweetest moments together. Below, we break down George and Amal Clooney’sentire relationship timeline, from the moment they met to where they are now.
July 2013: How They Met
George Clooney first met Amal Alamuddin in Lake Como, Italy in July 2013. While she was on her way to France, the future spouses were brought together by mutual friends and met at a dinner party at Clooney’s house. “I thought she was beautiful, and I thought she was funny and obviously smart,” the actor told The Hollywood Reporter. “She probably thought I was old.”
Clooney’s parents, Nick and Nina, were also at the dinner party and witnessed Clooney and Alamuddin’s instant connection. “Nina and I were actually the ones who answered the door when Amal came in,” Nick told People. “She introduced herself to us and we talked. She was obviously very charming, gorgeous and so clearly accomplished, but by the time we had supper that night, it was clear there was a kindness to her and an inclusiveness.”
He continued, “I really think by the time that first [meeting] was over, his and her fates were sealed, both of them. She was so remarkable and he was so remarkable around her.”
Summer 2013: The Courtship Begins
After the dinner party, Clooney and Alamuddin stayed in frequent contact while their relationship turned romantic. “We were writing each other, emailing, talking, mostly about what was going on in each other’s lives, and over a period of time it became clear we were more than just friends,” Clooney told THR.
October 2013: Their First Date
Months later, the couple publicly stepped out together for the first time in London. Clooney invited Alamuddin to visit him at Abbey Road Studios, where he was working. “That was a good first date,” he said. “Then we went for dinner… It was one of those places that was incredibly hip and chic. And when we came out, there were 50 paparazzi there. But she handled it like a champ. And pretty quickly, things escalated once I was in London.”
December 2013: Their First Vacation
Following her stay in London, the couple rang in the holidays together. “We spent Christmas together in Cabo San Lucas,” he told THR. “Then we went on a safari in Kenya. Amal loves giraffes; they’re her favorite animal. She went to this place called Giraffe Manor, where the giraffes stick their heads through the windows and kiss you.”
February 2014: George Starts Proposal Planning
Upon Clooney’s return to Los Angeles, he told a friend he knew he wanted to marry his girlfriend. “I had a picture of her, looking back, smiling at these giraffes,” he remembered, “and I said, ‘I think I’m going to ask her to marry me.'”
April 2014: The Proposal
On April 28, Clooney orchestrated an elaborate proposal for Alamuddin, but it didn’t quite go as planned. “I’m the cook in the family,” he recalled. “Believe me, Amal makes reservations. I did pasta of some form, not that impressive. And then over champagne, after dinner, I told her there was a lighter to light the candle in the drawer, and she reached back and pulled out a ring. And I did all the stuff, got down on my knee and did all the things you’re supposed to do. I had a playlist with my Rosemary [Clooney] songs on it and I was waiting for this song, ‘Why Shouldn’t I?’ It’s a really good song about why can’t I be in love? And it played, and she’s like, ‘Holy s—!’ And she just kept staring at the ring, going, ‘Oh, my God.'”
The pause was supposedly deafening. “It was 20 minutes of me on my knee, waiting for her to say yes, because she was so shocked. She only said yes when ‘Goody, Goody’ came on, which isn’t very romantic.” Alamuddin, of course, accepted the proposal (and the 7-carat, $750,000 emerald-cut ring), and they quickly began planning their wedding.
September 2014: George and Amal Clooney’s Wedding
Five months later, the couple wed in an elaborate ceremony in Venice, Italy on September 27, 2014. The bride wore an embroidered, off-the-shoulder Oscar de la Renta gown, while the groom wore a sleek tuxedo from Giorgio Armani. The couple said their vows under an arch of white flowers while 100 of their closest family members and friends, including Anna Wintour, John Krasinski, Emily Blunt and Cindy Crawford, looked on. Following the ceremony, the newlyweds celebrated late into the evening with their guests—but the party was far from over.
The next day the new Mr. and Mrs. Clooney hosted their guests for brunch and dinner in the City of Love. They closed out their wedding weekend with a civil ceremony on September 29.
May 2015: Met Gala
Despite being notoriously private, the couple attended their first Met Gala together in May 2015. Alamuddin wore a red John Galliano gown, while Clooney wore another Giorgio Armani tux.
Late 2016: Public Activism
Given Alamuddin’s career as a human rights lawyer and Clooney’s history of activism and public advocacy, they joined forces in late 2016 to start the Clooney Foundation for Justice. They continue to partner with nonprofits and organizations to bring justice to classrooms, courtroom and marginalized communities.
February 2017: The Clooneys Are Expecting
In a blink-and-you’ll-miss-it moment, Julie Chen casually announced on The Talk that the Clooneys were expecting. The actor gave his friend the go-ahead to announce their news live on television, and later opened up about the pregnancy to THR.
While in London for an ultrasound, the couple received some unexpected news from their doctor. “He goes, ‘Well, there’s one,'” Clooney recalled. “And I said, ‘Great.’ And then he goes, ‘And there’s the second one.’ And I was like, ‘What?’ We just sat there, staring at that piece of paper they give you, and I kept thinking there was a mistake.”
June 2017: The Twins Arrive
Four months later, the Clooney clan grew by two as they welcomed twins Ella and Alexander.
September 2017: Parents’ Night Out
The couple’s first public appearance after the birth of their children took them back to the romantic city where they were married at the Venice Film Festival.
May 2018: The Royal Wedding
The couple made an appearance at Prince Harry and Meghan Markle’s wedding on May 19, 2018. While they were in Windsor for the royal nuptials, they even joined Prince Charles for dinner at Buckingham Palace.
June 2019: Royal Dinner Dates Continue
One year after the royal wedding, the Clooneys are as close as ever with the Duke and Duchess of Sussex. After it was revealed that Baby Archie was born on his birthday, Clooney quipped to the Daily Mail, “It’s a big day for me, and now some royal child has been born!”
Joking aside, he revealed that he and his wife often host dinner parties with their royal friends. “We live not too far from one another and we have dinners and stuff and we’re friends with them for all the reasons that you’re friends with anybody,” he shared. “They’re just really nice, fun, kind people, they’re a very loving couple, and they’re going to be great parents.”