Prince Harry and Meghan Markle's relationship in pictures, from early dating to their iconic Royal Wedding and beyond

From some of their earliest pictures together to the latest shots of the Duke and Duchess of Sussex in action, a look back at Harry and Meghan's relationship milestones

A look back at Prince Harry and Meghan Markle's relationship through pictures
(Image credit: Getty Images)

In 2016, rumours were abound that the notorious bachelor Prince Harry was ready to settle down after finding love with a certain American actress. And, in a rarity, the rumours were true. 

Through the years, we've watched Meghan become a style icon - and the pair have continued to pursue charitable endeavours. But above all, they've given both romantics and cynics a reason to believe that love can conquer all. 

Let's take a look at their relationship milestone... 

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Prince Harry and Meghan Markle's relationship in pictures

1. The iconic 2020 umbrella shot

Prince Harry and Meghan Markle's relationship in pictures, from early 2017 dating to present day

(Image credit: Getty Images)

While not chronologically the first photo of the pair, no picture quite sums up the drama of their love story. From clandestine dates to defying families, they've weathered plenty of storms - but still hold on to their love for one another. 

This timeless shot of them caught in the rain was taken in London in 2020, as the pair attended The Endeavour Fund Awards. 

2. Their first Invictus Games together, 2017

Prince Harry and Meghan Markle's relationship in pictures, from early 2017 dating to present day

(Image credit: Getty Images)

Though the pair began dating in 2016, they managed to avoid photos together for quite some time. In fact, one of the earliest official appearances together was when Meghan joined Harry for the Invictus Games in Toronto, the charity he set up to honour those injured in active service. 

3. She said 'Yes' - announcing their engagement, 2017

Prince Harry and Meghan Markle's relationship in pictures, from early 2017 dating to present day

(Image credit: Getty Images)

Harry and Meghan announced their engagement on November 27, 2017. The pair posed for photos outside Frogmore Cottage, which was their home while they resided in the UK.

4. How did Harry propose? The sweet - and normal - details

Prince Harry and Meghan Markle's relationship through the years in pictures

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More details of their engagement were revealed in Prince Harry and Meghan Markle's Netflix docuseries and his sensational tell-all memoir, Spare. 

Harry shared that he popped the question on "just a standard, typical night for us." Meghan added, "Just a cozy night... what were we doing? Roasting chicken and... And it was just... just an amazing surprise, it was so sweet and natural and very romantic. He got on one knee." 

5. The touching details of Meghan Markle's engagement ring

Prince Harry and Meghan Markle's relationship in pictures

(Image credit: Getty Images)

Meghan's engagement ring was made of three stones, a style known as a trilogy ring. The cushion-cut centre diamond of her engagement ring was estimated to be roughly three carats and was sourced from Botswana, a place with emotional significance to both she and Harry. 

The smaller side diamonds came from the personal collection of Princess Diana.

6. Meghan's first Christmas with the royal in-laws, 2017

Pictures of Prince Harry and Meghan Markle's relationship over the years

(Image credit: Getty Images)

Fresh from their engagement, Meghan Markle spent her first Christmas at Sandringham with the Royal Family. Fans absolutely loved catching a sight of the future Duchess of Sussex on the traditional Christmas morning walkabout. 

Of the first Christmas, Meghan has previously said, "I remember so vividly the first Christmas at Sandringham. Calling my mom, and she's like, 'How's it going?' and I said, 'Oh my gosh, it's amazing. It's just like a big family like I always wanted.'"

7. Their first appearance together after the engagement, 2017

Pictures from Harry and Meghan's relationship over the years

(Image credit: Getty Images)

Less than a week after announcing their engagement to the world, Harry and Meghan appeared in Nottingham to increase HIV/AIDS awareness. 

8. A pre-wedding appearance, April 2018

Prince Harry and Meghan Markle's relationship in pictures

(Image credit: Getty Images)

Just a month before their wedding, Prince Harry and Meghan Markle were spotted attending the team trials for the 2018 Sydney Invictus Games. Meghan looked on as her husband-to-be explained what was going on, sharing arguably his biggest passion. 

9. The Royal Wedding, May 2018

Prince Harry and Meghan Markle's relationship through the years in pictures

(Image credit: Getty Images)

The wedding of Prince Harry and Meghan Markle was held on Saturday 19 May 2018 in St George's Chapel at Windsor Castle.

Almost 23.7 million households watched the wedding of Prince Harry and Meghan Markle in May 2018, amounting to a total of 29.19 million viewers. It remains the most popular royal wedding, according to Google searches over the years since they said "I Do."

10. Meghan's wedding dress details

Prince Harry and Meghan Markle's relationship through the years in pictures

(Image credit: Getty Images)

Meghan's stunning silk gown was designed by Givenchy artistic director, Clare Waight Keller. The veil was embroidered with flowers representing the countries of the Commonwealth plus the California poppy, a nod to Meghan's home state, and a wintersweet, a flower that grows at Kensington Palace. 

The dress was made of silk with three-quarter-length sleeves, an open boat neckline and a train with built-in triple silk organza underskirt. 

11. A quick change for the wedding after-party

Pictures of Prince Harry and Meghan Markle's wedding

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Prince Harry and Meghan Markle headed to their evening reception in an icy blue vintage Jaguar.

Both the bride and the groom changed for the party. Prince Harry opted for a tuxedo, and Meghan chose a second bridal gown, made by designer Stella McCartney.

12. Trooping the Colour 2018, Meghan Markle's first

Prince Harry and Meghan Markle's relationship in pictures

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A few weeks after their wedding, the newly minted Duchess of Sussex joined Prince Harry for her first ever Trooping the Colour. While never confirmed, it was reported the two slipped away for a private honeymoon in Canada before returning for the annual royal parade. 

13. They're expecting! The couple announce they are pregnant, October 2018

Pictures of Harry and Meghan throughout their relationship

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On October 15, 2018, the Royal Family's official accounts shared the happy news that Harry and Meghan were expecting their first child. 

The posts read, "Their Royal Highnesses The Duke and Duchess of Sussex are very pleased to announce that The Duchess of Sussex is expecting a baby in the Spring of 2019.

Their Royal Highnesses have appreciated all of the support they have received from people around the world since their wedding in May and are delighted to be able to share this happy news with the public."

14. The Sussexes go down under, October 2018

Prince Harry and Meghan Markle's relationship in pictures

(Image credit: Getty Images)

The newlyweds didn't have too much time to live in the honeymoon phase - in October 2018, months after the wedding, they jetted off for an official royal tour. The 16 day event included trips to New Zealand, Fiji and Australia. 

15. Inseparable

Prince Harry and Meghan Markle's relationship in pictures

(Image credit: Getty Images)

The couple showed endless displays of affection while continuing their tour of Australia. 

16. His job is just... beach - Harry and Meghan relax

Prince Harry and Meghan Markle's relationship in pictures

(Image credit: Getty Images)

The pair kicked back and relaxed while visiting Bondi Beach. It might have been a case of foreshadowing as the two would eventually leave the UK for good and settle by the beach in Montecito, California. 

17. Dressed down in New Zealand

Prince Harry and Meghan Markle's relationship in pictures

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Despite being busy at work, the couple would catch some quality time together, enjoying dressed down, casual strolls through Wellington, New Zealand. 

18. Christmas 2018 - their last with the royals

Prince Harry and Meghan Markle's relationship in pictures

(Image credit: Getty Images)

As it would turn out, 2018's Christmas appearance for the Sussexes would be their last (to date). 

The year after, the couple spent Christmas with Meghan's mother, Doria Ragland, in California and in 2020, the Covid crisis meant that the late Queen Elizabeth II couldn't host a big family gathering. And then, of course, the couple left royal life before 2021's festivities came around.  

19. A pregnant Meghan steps out for her first joint engagement with Harry in 2019

Prince Harry and Meghan Markle's relationship in pictures

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The glowing Meghan and the proud father-to-be stepped out in January 2019 for their first joint engagement of the year. Meghan cheered up the wintry weather in Birkenhead with a bold red coat and purple dress. 

20. Prince Harry and Meghan Markle visit Morocco, February 2019

Pictures of Prince Harry and Meghan Markle

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Conscious of her upcoming due date, Meghan and Harry squeezed in a three-day tour of Morocco in late February 2019. 

21. Archie is born, May 2019

Prince Harry and Meghan Markle's relationship in pictures

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Archie Harrison Mountbatten-Windsor was born at 05:26am on 6 May 2019 at the Portland Hospital in London. He was the first child of the Duke and Duchess of Sussex. 

Unlike previous royal births, there was no immediate photo-call at the hospital steps but he was later unveiled to the world on 8 May with adorable photos of the family.

22. Archie's first overseas trip with mum and dad, September 2019

Prince Harry, Meghan Markle and Prince Archie in South Africa, 2019

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At just four months old, Prince Archie became a jetsetter, joining his royal parents for a visit to South Africa. The young prince even got to meet Archbishop Desmond Tutu. 

23. Parents day out - South Africa tour, 2019

Pictures of Prince Harry and Meghan Markle

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Harry and Meghan made time to enjoy some kid-free time during their tour of South Africa. They met with fans in Cape Town, and the Duchess of Sussex chose to wear a beautiful black and white dress by Mayamiko, a designer who uses fabrics from Malawi, which she paired with black espadrilles. 

24. Attending the WellChild Awards, October 2019

Pictures of Prince Harry and Meghan Markle's relationship over the years

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Meghan Markle and Prince Harry attended the WellChild Awards together to meet with children and young adults who are struggling with serious illnesses. Meghan was there to support her husband who broke down in tears while discussing his journey to fatherhood in a moving speech. 

25. 'Megxit' is announced - January 2020

Prince Harry and Meghan Markle's relationship in pictures

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On January 8, 2020, Prince Harry and Meghan Markle announced their decision to “step back” from their roles as senior royals. They revealed their initial intentions to split their time between the US and the UK in a move that was somewhat controversially dubbed "Megxit."

26. Matching in red, March 2020

Prince Harry and Meghan Markle's relationship in pictures

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Harry and Meghan attended the Mountbatten Music Festival at the Royal Albert Hall in London on March 7, 2020. They stunned crowds with their colour coordinated regal red ensembles. 

Their appearance at the festival was somewhat poignant as it would be one of the last times Harry would get to wear full military regalia, after their decision to step down from royal duties was announced a few months earlier. 

27. Their last ever royal engagement, March 2020

Prince Harry and Meghan Markle's relationship in pictures

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Prince Harry and Meghan, Duchess of Sussex marked their final engagement as senior members of the royal family on March 9, 2020, attending the annual Commonwealth Service at Westminster Abbey. 

Meghan arrived in an emerald green dress, with a matching cape, bag and fascinator. Harry matched her subtly in a blue suit with a green lining

28. They announce baby #2, February 2021

Pictures of Prince Harry and Meghan Markle's relationship

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After laying low following their move to Canada (and then the US), Meghan and Harry delighted fans with the reveal that they were expecting their second child. The happy news was shared on Valentine's Day with a gorgeous photoshoot showing the pair barefoot and relaxing outdoors. 

Their second child - daughter Lilibet - would be born on June 4, 2021. Not many pictures of the young princess are available, but Harry and Meghan shared the first photo through their Christmas card. 

29. Meghan joins Harry on stage for first appearance since Lilibet, September 2021

Pictures of Prince Harry and Meghan Markle

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Meghan joined Harry at the Global Citizen Live event on September 25, 2021. It was Meghan's first public appearance since having Lilibet. 

Speaking about The Duke and Duchess of Sussex's support of the cause to make Covid vaccines readily available to millions, the organisers said, "Two of the strongest voices on vaccine equity are joining this once-in-a-generation event."

30. Glammed up for a special cause, November 2021

Pictures of Prince Harry and Meghan Markle's relationship throughout the years

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Meghan shut down the red carpet in a vivacious red gown on November 10  as she joined Prince Harry at the 2021 Salute to Freedom Gala. 

Meghan wore a regal red gown with a plunging neckline and an A-line style train, and Harry complemented his wife in a black suit and bow tie with a crimson poppy pinned to his lapel. 

Prince Harry, who served in the British army for 10 years, presented the inaugural Intrepid Valor Award to five recipients.

31. Back in Europe - with a special visit, April 2022

Pictures of Prince Harry and Meghan Markle

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Prince Harry and Meghan Markle stopped by Windsor Castle on their way to the Invictus Games in The Hague, the Netherlands to visit Queen Elizabeth and the then Prince Charles.

It was their first reunion since 2020, though Harry had come back solo for the funeral of Prince Philip. 

32. They're both back - the couple's first joint appearance in the UK, June 2022

Prince Harry and Meghan Markle's relationship in pictures

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Prince Harry and Meghan Markle finally returned to the UK for the first official appearance since 2020 in the summer of 2022. 

Harry had previously come alone, for the funeral of Prince Philip, but both the Duke and Duchess of Sussex returned for a service of thanksgiving for the reign of Queen Elizabeth II to honour her Platinum Jubilee.

33. Back again, for a very sad reason, September 2022

Pictures of Prince Harry and Meghan Markle

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Meghan accompanied her husband as he returned to the UK following the death of Queen Elizabeth in September 2022. 

In a move that surprised royal fans - and gave them some happy news during the national mourning period - Harry and Meghan joined Prince William and Kate Middleton for an official walkabout. It was the first time the four of them had been seen together since March 2020. 

34. Attending the Queen's funeral, September 2022

Prince Harry and Meghan Markle at Queen Elizabeth II's funeral

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The state funeral of Queen Elizabeth II was a moment for the history books. Harry and Meghan were reunited with the Royal Family for the service. The couple were thought to have returned home to California the day after attending the funeral service. 

35. Celebrating Meghan in New York City, 2023

Pictures of Prince Harry and Meghan Markle

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Meghan Markle was the guest of honour for the Ms Foundation awards in Manhattan in May 2023. 

While Meghan sparkled in a strapless, golden Johanna Ortiz ensemble with a matching Carolina Herrera clutch bag, Harry beamed with pride as he watched his wife pick up the 2023 Women of Vision Award.

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Jack Slater
Freelance writer

Jack Slater is not the Last Action Hero, but that's what comes up first when you Google him. Preferring a much more sedentary life, Jack gets his thrills by covering news, entertainment, celebrity, film and culture for woman&home, and other digital publications.

Having written for various print and online publications—ranging from national syndicates to niche magazines—Jack has written about nearly everything there is to write about, covering LGBTQ+ news, celebrity features, TV and film scoops, reviewing the latest theatre shows lighting up London’s West End and the most pressing of SEO based stories.