Introduced to the world as a shy, demure teen, Diana quickly blossomed into a once-in-a-generation princess, loved around the world for her warmth, compassion and devotion, reports The Early Show's Erica Hill.
"Obviously I would have loved to have met her and she's obviously an inspirational woman to look up to," said Kate Middleton at the announcement of her engagement to Prince William.
With Tuesday's official announcement, the parlor game of comparing Kate to William's late mother kicked into high gear - beginning with the ring.
"It's my mother's engagement ring, so I thought it was quite nice because obviously she's not going to be around to share in the fun and excitement of it," said William. "All this was my way of keeping her close to it all."
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Thirty years earlier, in a strikingly similar setting, the same 18-carat sapphire and diamond stunner graced the hand of Lady Diana Spencer.
"There were three of them at the engagement yesterday, a bit crowded of course," Andrew Morton, whose 1992 biography of Diana sparked an uproar, told CBS' "The Early Show". "Diana - the ghost of Diana - hung very heavily there and, yes, I mean she always said to me that the throne will jump a generation, jump Prince Charles and go to William. And she was always grooming William for a happy life and, also, for a fulfilling life, but also where he would do his duty. I think Kate would be a very solid partner for him, far more than the Queen and Prince Philip."
Morton speculated that Diana would "thrilled but a little jealous" about the engagement.
"I think, because she's been approaching 50 now and seeing the baton, certainly the fashion baton had been passed from one generation to the next so I'm sure she would be advising Kate, but also a bit of sadness [at] losing a son, as well,"
Just 19, Diana dated Charles for only six months before their engagement, a far cry from the more than eight-year courtship for this royal couple.
"I'm also glad I had the time to grow up and understand myself more as well," said Kate.
Often described as confident, Kate once quipped the prince was lucky to have her.
"Everyone can see she's not like Diana," said Ingrid Seward, editor of Majesty magazine. "She's not a troubled girl from a broken home. She's a very easy going, happy well-adjusted girl."
Despite her aristocratic background, Diana's parents' bitter divorce haunted her.
Her own marriage -- arranged for Prince Charles -- was far from the fairy tale she'd dreamed of as a little girl.
Yet there is a feeling that this royal union will be different. That Kate Middleton, the commoner backed by a strong family, who as a teen had a poster of her fiance tacked up in her dorm room, will write her own ending -- perhaps a true fairy tale at last.
"It's about carving your own future," said William. "No one is trying to fill my mother's shoes. What she did is fantastic. It's about making your own future and your own destiny and Kate will do a very good job of that."
What is clear that William is taking on the role of protector - both of his mother's memory - and of his bride-to-be.
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