After 11 films, including a 1954 Oscar-winning turn as Bing Crosby's dowdy spouse in The Country Wife, Kelly met the 31-year-old Prince Rainier III of Monaco while doing a photo shoot at his palace in 1955. They began exchanging letters and Rainier, who was under pressure to produce an heir, went to America in December of that year to meet her family. He proposed three days later.
Prince Charles had been seeing Diana's older sister, Lady Sarah, but began to focus on Diana after they both were guests at a country getaway in 1980. That led to a sailing weekend on a yacht and an invitation to Balmoral, the royal family's Scottish residence, to meet Charles' family. After a courtship in London, the prince, 34, proposed on Feb. 6, 1981 — although the engagement was kept secret for several weeks.
Grace's ring was originally a tasteful Cartier eternity band of rubies and diamonds. But after checking out the rock candy on the fingers of other Hollywood ladies, the prince upgraded to a 10.5-carat emerald-cut diamond nestled between two baguettes, also made by Cartier. Grace wore it in the final film she shot, High Society.
Diana's ring featured 14 solitaire diamonds circling a 12-carat oval blue Ceylon sapphire set in 18-karat white gold, which resembled her mother's engagement ring. The piece was made by Garrard, then the crown jewelers, and the design was later available in the company's catalog.
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