I must admit I was VERY surprised when she started dating him and going on to get engaged and married back in the day. Would never have seen him as much of a catch -he was such a wannabe going on every reality TV singing competition and losing, in the early 00's. Pippa, on the other hand, no matter what kind of optics she spun about how 'relatable' she was with her high street clothes before building her 'empire', was never like the rest of us. She is extremely well connected (her brother's Godfather being Sir Tony O'Reilly, old money, one of Ireland's first billionaires so go figure). She's a silver spoon and Lego knew he'd landed on his feet with her.