Diana was firstly educated at Silfield School in Kings Lynn, Norfolk, then at Riddlesworth Hall in Norfolk and at West Heath Girls' School (later reorganised as the New School at West Heath, a special school for boys and girls) in Sevenoaks, Kent, where she was regarded as a poor student, having attempted and failed all of her O-levels twice. In 1977, at the age of 16, Diana left West Heath and briefly attended Institut Alpin Videmanette, a finishing school in Rougemont, Switzerland. At about that time, she first met her future husband, who was dating her sister, Lady Sarah. Diana reportedly excelled in swimming and diving and is said to have longed to be a ballerina but did not study ballet seriously and at 5'10" was too tall for such a career.

Once it was clear that Diana would not earn any formal educational qualifications, Diana begged her parents to allow her to move to London , a request granted before she was seventeen. An apartment was purchased for Diana at Coleherne Court in the Earls Court area, she lived there until 1981 with three flatmates. During that period, Diana studied for a Cordon Bleu cooking diploma, although she apparently hated cooking, and worked at Madame Vacani's Dance Academy in Kensington, but resigned because she didn't like the pushy stage school parents. Lady Diana filled time as a cleaner and a cocktail waitress, before finding a job as a part-time aide at the Young England Kindergarten nursery school.

Prince Charles' love life had always been the subject of press speculation, and he was linked to numerous glamorous and aristocratic women. In his early thirties, he was under increasing pressure to marry. Legally, the only requirement was that he could not marry a Roman Catholic; a member of the Church of England was preferred. In order to gain the approval of his family and their advisers, any potential bride was expected to have a royal or aristocratic background, be a virgin, as well as be Protestant. Diana met these qualifications. They married at St Paul's Cathedral on 29 July 1981, watched by a global audience of almost one billion.

In April 1987, Diana Princess of Wales was one of the first high-profile celebrities to be photographed touching a person infected with HIV at the 'chain of hope' organisation. Her contribution to changing the public opinion of AIDS sufferers was summarised in December 2001 by Bill Clinton at the 'Diana, Princess of Wales Lecture on AIDS': An iconic presence on the world stage, Diana was noted for her sense of style, charisma, humour and high-profile charity work, yet her philanthropic endeavours were overshadowed by her difficult marriage to Prince Charles.