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Prince Andrew and Sarah Ferguson

After having a bit of a reputation as a playboy in his youth, Prince Andrew married Sarah Ferguson in 1986. Both age 26, the couple were high-spirited and less formal than some of their royal relatives. They had two daughters together: Princess Beatrice and Princess Eugenie. However, Andrew's military career and their relatively low income for a royal lifestyle caused fractures for the Duke and Duchess of York.

Like Charles and Diana, the couple first agreed to separate in 1992. However, pictures soon surfaced of Sarah with her financial adviser John Bryan, which caused a final rift (and is the reason Prince Philip still refuses to speak to Sarah even to this day). The couple divorced in 1996 but remained close: they still live together and raised their two daughters together as a perfectly content divorced couple.