James Middleton was 23 years old when his eldest sister married the future King of England.
An estimated two billion people worldwide watched the wedding of Kate Middleton to Prince William, and the day was declared a bank holiday in the United Kingdom.
Just over a month ago, on the 20th of May 2017, James’ sister Pippa, four years older than him, married James Matthews, a former professional racing driver, current hedge fund manager and heir of David Matthew, Laird of Glen Affric, Scotland.
His eldest sister is the future Queen of England.
His middle sister might one day be the Lady of Glen Affric.
And James, now 29, has no royal ambitions whatsoever.
LISTEN: Why Kate Middleton is always kneeling. Post continues below.
James told the Daily Mail , “It’s always been, whether at school or now, that I am Pippa and Catherine’s little brother. It’s probably going to be the story of my life. [But] I am James Middleton. I am very proud to be ‘the little brother of…’ but, equally, they are proud that I am who I am.”
Growing up, the Middleton sisters were athletic and studious. By his own admission, James was never academic and struggled with dyslexia.
James attended the University of Edinburgh, the same university as Pippa, after having to resit his A-levels at a local college.
Much to his parents dismay, James dropped out of university after one year. But he never once regretted his decision.
Instead, he travelled the world, visiting Australia where he learned to sail. Simply, James says, he “found himself”.
"I discovered my confidence, my skills, and not just ones that were placed in front of me because that’s what my peers were doing," he reflected.
When he returned, Kate's relationship with William had hit the press.
"I used to be first up in the morning to make sure I could get to the papers and rip out any stories about my sister, so nobody would see them and there would be no conversations about them," James told the Daily Mail.
Then, in April 2011, James' eldest sister married Prince William in the wedding of the century, and his own life well and truly became public property.
Along with his sister Pippa, James' lifestyle was suddenly the stuff of tabloid fodder. Whether it was stumbling out of a nightclub, or being pictured with British television personality and actress Donna Air, James' life was now 'ours'.
Years before, James had launched the Cake Kit Company, which provided DIY kits and ingredients for festive party cakes.
"I knew that that mouthful of academic prescription was not going to do it for me," he told GQ at the time. "My dream, which came to me when I was flying back up to Edinburgh after a weekend home, was to build a cake empire."
Unfortunately, in 2015, his 'cake empire' collapsed.
His relationship with Air, however, was flourishing. The media personality, nine years older than James, was being splashed all over the social pages.
"When you see yourself on a marshmallow, or your loved one or your pet, you have a little moment with that little marshmallow. There aren't many products in the world like that," he told the Cut. "I'm very much surrounded by [marshmallows], but I still love them [...] Marshmallows are sort of like an essential candy. They're pillows of sweetness."
And James, in his own right, is undoubtedly a very interesting character.