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

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.

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.

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.

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.

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.

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?

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.

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!

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.

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.

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.

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

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.

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?

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.”

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.

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.

“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.

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

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

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

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