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From the world’s most famous bridesmaid to the ultimate bride: Pippa Middleton & James Matthews’ surprising romance in pictures

The couple tied the knot in 2017.
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If you cast your minds back to 2011, Pippa Middleton, the younger sister of Catherine, Duchess of Cambridge, had a very different life.

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A bridesmaid at her elder sister’s show stopping royal wedding, the world was utterly enchanted by the brunette beauty, who oozed sophistication and grace, much like her royal sibling, as she made her grand entrance into Westminster Abbey in front of a global audience.

But while the eye-catching bridesmaid instantaneously became one of the worlds most desirable bachelorettes (seriously, even Prince Harry was touted as a potential suitor), it seems there was another, very unique happily ever after awaiting the most iconic bridesmaid of 2011.

Enter James Matthews, a hedge fund manager also from the UK, who regularly mixed in the Middleton family’s prestigious social circles.

But while their romance seemed to be picturesque as anything, these two have a relationship that’s had its ups and downs, stemming right back to before we even knew whether Kate and Wills would make it or break it.

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Despite their bumpy past, the pair went on to tie the knot in a lavish wedding at St Marks’s Church in Englefieldon May 20 2017.

Pippa stunned in an incredible lace creation by Giles Deacon, featuring a high-neck, capped sleeves, a heart-shaped back and a full skirt.

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Fast forward four years later and the pair are now the proud parents to a two-year-old son called Arthur and a newborn daughter called Grace, who was born in March.

As they ring in their four-year wedding anniversary, take a look back at Pippa and James’ tumultuous, yet terrific tale of love.

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Middleton sisters in 2007

In 2007, Pippa, who was in her hey-day of attending lavish soirees with Kate as they rode our their roaring 20s, met James during a visit to St Barts when she stayed at Eden Rock, a luxury hotel on the Caribbean island owned by James’ parents. Interestingly, the pair were not romantically linked off the bat.

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Friendship first

After that fateful stay, in which Pippa struck up a simple friendship with James, the pair remained in touch as she continued to mix with James’ family and wider circle in the years following.

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2011 Royal Wedding

In 2011, Pippa made headlines across the world when she pulled off the ultimate role as Maid of Honour at her sister Kate’s wedding to Prince William. At the time, the world was in throes of confusion as to who she was dating, whether she was single and of course, whether Prince Harry would neatly become her husband.

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James Matthews friendship with her brother

Of course, the Prince Harry match up was a little far-fetched. Instead, in 2012, Pippa was linked back to James Matthews, who was already good pals with her younger brother James Middleton (pictured). It’s understood they went on a series of dates together.

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Pippa & Nico date for three years

But don’t get too ahead of yourselves. In 2013, Pippa was then linked to one Nico Jackson, an affluent stockbroker, who she dated for almost three years.

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Pippa & James unite for bike race in 2015

In 2015, news of Pippa and Nico’s split was made known to the world, which left a question mark over who she was dating. During that time, Pippa and James remained close and were even photographed together following a bike race (pictured). So were they, or weren’t they a thing?

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A day out at Wimbledon together

The answer, was a resounding yes. Pippa and James’ relationship became common knowledge in 2016, especially as things moved extremely quickly between the pair. It was reported they moved in together in May, with James later popping the question to Pippa later that year.

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Christmas of 2016

As we all know with royals in years gone by, if they take them to Christmas mass, they’re as good as married. Pippa and James were pictured attending church with the Middleton clan on December 25, 2016 in Bucklebury, Berkshire. And thus, the pair’s relationship was cemented for good!

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Pippa & James get married in 2017

A full 10 years after their first meeting, the couple made things properly official on May 20, 2017 in a glorious wedding ceremony at St Marks’s Church in Englefield.

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Pippa’s beautiful wedding dress

As expected, Pippa wowed in a stunning bridal gown by Giles Deacon. Featuring a beautiful lace bodice with short sleeves and a high neck, the most iconic bridesmaid of the early 2010s had finally become the bride – and boy was it worth the wait.

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Kate & Charlotte at Pippa’s wedding

Of course, the ceremony featured some very familiar faces, with Duchess Catherine returning the favour for her sister six years on from her own wedding in a beautiful blush ensemble. A young Princess Charlotte also stole hearts as a bridesmaid in the official party.

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On the church steps

A fairytale indeed! Pippa and James’ nuptials was the ultimate happily ever after.

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Pippa & James announce pregnancy

First comes love, then comes marriage, then comes … the baby announcement we’d always hoped for! In June 2018, Pippa revealed her pregnancy in her regular column for Waitrose magazine.

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A day out at Wimbledon

And thus began a plethora of stunning maternity outfits we just couldn’t get enough of. Seriously, how chic is this summery white lace creation?

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Welcome Arthur!

In October 2018, Pippa and James welcomed their new baby son, Arthur Michael William Matthews, who arrived safely at London’s Lindo Wing. At the time, a spokesperson told Hello!: “Everyone is delighted and mother and baby are doing well.”

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Pippa & James value privacy

Pippa and James have continued to make various appearances together (though pictures rarely show their baby son) at the annual Wimbledon tournament, as well as various royal outings involving Kate’s wider family.

Opening up about motherhood, the 38-year-old revealed swimming lessons have been a beautiful way to bond with her son. “Starting my son Arthur swimming at four months old has given him confidence and enjoyment in water. Swimming is one of our favourite activities. The exercise helps guarantee sound daytime sleeps, and the movement has improved his digestion,” she said.

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Welcome Grace!

Arthur’s a big brother! In March 2021, it was confirmed Pippa and James had welcomed their second child together – a daughter called Grace Elizabeth Jane.

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Duke & Duchess of Cambridge release statement

“The Duke and Duchess are absolutely overjoyed by the happy news. She’s perfect, everyone is overjoyed at such a happy arrival,” a source close to the Duke and Duchess of Cambridge revealed to People shortly after Grace’s arrival.

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St. Luke’s Church visit

In December 2019, Pippa and James couldn’t wipe the smiles off their faces as they left St. Luke’s Church in London.

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Date night

In January 2021, Pippa and James enjoyed a date night at London’s Royal Albert Hall to watch Cirque du Soleil’s Luzia show.

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United front

Pippa and James gazed adoringly at each other at a Wimbledon match in July 2021.

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Happily ever after…

From friends to soul mates – it’s been a right, royal journey.

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