James Matthews is a self-made millionaire who, like Kate and Pippa, is descended from a coalmining family that lived and worked in the North of England. He enjoyed a privileged upbringing thanks to his father's rags-to-riches story in the motor trade and attended a pubic school along side future celebrities Stephen Fry and Rowan Atkinson. He will fit comfortably into the royal circle of his new friends and family.
Pippa Middleton's fiancee, James Matthews, will probably have little trouble fitting in with the royal family. As a hedge fund manager and the longtime boyfriend of Middleton, he is certainly part of the upper class elite that usually gets along socially in Britain. I think the transition should be fairly seamless.
Pippa Middleton's hedge-fund beau will fit in with her royal relatives. However, this all begs the real question - who the heck cares? How shallow does one's life have to be to put one ounce of energy into following, let alone caring, about what Pippa Middleton does. It's no one's business. Get a life, people.
I feel that James Matthew's will do just fine with Pippa Middleton's family. He certainly began on the right foot by asking her father, Michael, for his permission to propose to her. Both parents are reported to be thrilled about the pending marriage. I see no roadblocks whatsoever for the romantic traditionalist.