But all her heartache was forgotten this week when James Matthews, 40, got down on one knee and popped the question.
So, who exactly is this hopeless romantic who has swept Pippa off her feet with a diamond sparker reportedly worth more than US$250,000? [see video below for a close-up!]
Here are five important ‘must-knows’ about James before the big day.
1. His brother was lost on Everest
Younger brother Michael, pictured below left, disappeared on Mt Everest in 1999 after becoming the youngest Brit to conquer the world’s highest mountain at the age of 22. Michael is believed to have perished in the “death zone”, a treacherous region above 8000m, as he fought his way down through blizzard-like conditions, the Mirror reported.
His body has never been found. The brothers’ self-made millionaire father, David, battled for years to prove that Michael’s death was caused by the negligence of his mountain guides.
2. His other brother is a reality tv star
Spencer Matthews stars in London’s hit reality show, Made in Chelsea. The show follows the lives of wealthy London socialites in their twenties who are born into a life of luxury. Think Rich Kids of Beverly Hills, but in London.
3. He’s a sports junkie
And especially loves to unwind on the slopes. Husband to be James is photographed skiing next to Pippa at the Birkebeiner ski race in Norway. The couple finished the skiing marathon in around six hours. We think there must be some friendly athletic competition between these two love birds.
4. He’s Got The Brains
James manages a hedge fund and is the chief executive of Eden Rock Capital Management Group. James established the management group more than 10 years ago, according to the International Business Times. He named the group after his parents hotel in St. Barths.
5. He Attended The Same School As Prince Harry & Prince William
True story! Looks like James, Prince William, and Prince Henry all share something in common. All three boys attended Eton College, an English boys’ independent boarding school in Windsor, England. Don’t be fooled by the name though, it’s a boarding school not a traditional college.