After Middleton's then-boyfriend, Alex Loudon, broke up with her because he couldn’t handle her sudden fame, Matthews connected with Middleton and the two dated for a few months. Their relationship didn't last long, with reports citing that their 8-year age difference was a problem for James. Middleton then went on to date Nico Jackson for three years and after they broke up, she reconnected with Matthews in late 2015.
2. He's, like, super rich.
The Matthews are a very wealthy family. In 1995, they purchased the hotel Eden Rock St. Barth's, which is related to Antibes’s famous Hôtel du Cap-Eden-Roc, and also own massive estates. For his part, according to The Evening Standard, James' net worth was estimated at $2.6 billion in 2016, establishing himself by creating the hedge fund Eden Rock Capital Management and making millions. He also owns a $22 million West London home, where Pippa is currently living. Plus, that giant rock Pippa now sports is worth a reported $323,550!
3. He's got a great title, which Pippa will inherit.
Matthews' father, David, currently holds the Scottish title of Laird of Glen Affric, which means that he owns the 10, 000-acre Glen Affric property in the Scottish Highlands. As the eldest son, after his father passes, James will inherit the title and become Laird, while Pippa will become Lady of Glen Affric. She'll then have a title just like her sister Kate, the Duchess of Cambridge.
4. He was a professional race car driver, and a really good one!
Matthews participated in a number of races in the '90s, such as as the British Formula 3 Championship. In 1994, at the age of 18, he won the British Formula Renault Championship for Manor Motorsport and the Eurocup Formula Renault.
5. His brother, Michael, died descending Mt. Everest.
James' brother, Michael, died at the age of 22 while he was descending Mt. Everest. He became the youngest Briton to climb the peak. Following his death, the family set up the Michael Matthews Foundation, which works to provide education for children in remote and impoverished areas. In 2016, Pippa and her brother, James, raised money for the organization by taking part in the Otillo race and she climbed the Matterhorn in Switzerland in Michael's honor.
6. His other brother, Spencer, is a reality star.
James' 27-year-old brother, Spencer, is a former British Bachelor whose claim to fame came as an original cast member of the 2011 reality show Made in Chelsea. In 2012, he starred on the U.K. version of The Bachelor, and then returned to Made in Chelsea after not finding his one true love. Spencer was also seen on I'm a Celebrity, Get Me Out of Here! and hosted the talk show Loose Women in 2016.
James is a big fan of skiing and he and Pippa have been seen hitting the slopes. The two competed in the Birkebeiner ski race in Norway and have participated in the London to Brighton charity bike ride together. Additionally, in 2008, he ran the 156-mile Marathon des Sables through the Sahara and enjoys watching tennis matches at Wimbledon.