Reading the link about Chelsey's family and her idyllic African childhood, barefoot on the farm, makes me think this is partly what links him he: an ideal of what his life could be.
She represented a free life away from the UK, in nature with a happy loving family. I think that's what he really yearned for.
Instead he's ended up in a media Hollywood bubble, being on the celebrity circuit, selling his life for money, obsessed with the past, as hounded as ever and estranged from both families.
I think that's why he took Meghan to Africa for one of their first dates he was trying to create the possibility of this dream life that had been shown to him years ago.
But she was never going to be the women for that.
He is a sad person.
What is his life now? Can he create a fulfilling life?