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In February 1932, Diana met Sir Oswald Mosley at a garden party at the home of the society hostess Emerald "Maud" Cunard.
He soon became leader of the newly formed British Union of Fascists, and Diana's lover; he was at the time married to Lady Cynthia Curzon.
Diana left her husband Bryan Guinness, 'moving with a skeleton staff of nanny, cook, house-parlourmaid and lady's maid to a house at 2 Eaton Square, round the corner from Mosley's flat', but Sir Oswald would not leave his wife. Quite suddenly, Cynthia died in 1933 of peritonitis. Mosley was devastated by the death of his wife, but later started an affair with her younger sister Lady Alexandra Metcalfe.
Owing to Diana's parents' disapproval over her decision to leave Guinness for Mosley, she was briefly estranged from most of her family. Her affair and eventual marriage to Mosley also strained relationships with her sisters. Initially, Jessica and Deborah were not permitted to see Diana as she was "living in sin" with Mosley in London. Deborah eventually got to know Mosley and ended up liking him very much. Jessica despised Mosley's beliefs and became permanently estranged from Diana after the late 1930s. Pam and her husband Derek Jackson got along well with Mosley. Nancy never liked Mosley and, like Jessica, despised his political beliefs, but was able to learn to tolerate him for the sake of her relationship with Diana. Nancy wrote the novel Wigs on the Green, which satirised Mosley and his beliefs. After it was published in 1935 relations between the sisters became strained to non-existent and it was not until the mid-1940s that they were able to get back to being close again.
The couple rented Wootton Lodge, a country house in Staffordshire which Diana had intended to buy. She furnished much of her new home with much of the Swinbrook furniture that her father was selling. The Mosleys lived at Wootton Lodge along with their children from 1936 to 1939.
In 1934, Mitford went to Germany with her then 19-year-old sister Unity. While there, they attended the first Nuremberg rally after the Nazi rise to power. A friend of Hitler's, Unity introduced Diana to him in March 1935. They returned for the second rally later that year and were entertained as his guests at the 1935 rally. In 1936, he provided a Mercedes-Benz to chauffeur Diana to the Berlin Olympic games. She became well acquainted with Winifred Wagner and Magda Goebbels.
Diana and Oswald wed in secret on 6 October 1936 in Nazi propaganda chief Joseph Goebbels' drawing room. Adolf Hitler, Robert Gordon-Canning and Bill Allen were in attendance. The marriage was kept secret until the birth of their first child in 1938. In August 1939, Hitler told Diana over lunch that war was inevitable.
Mosley and Diana had two sons: Oswald Alexander Mosley (born 26 November 1938) and Max Rufus Mosley (born 13 April 1940). Hitler presented the couple with a silver framed picture of himself.
On 29 June 1940, eleven weeks after the birth of her fourth son Max, Diana was arrested (hastily stuffing Hitler's photograph under Max's cot mattress when the police came to arrest her) and taken to a cell in F Block in London's Holloway Prison for women. She and her husband were held without charge or trial under the provisions of 18B, on the advice of MI5. The pair were initially held separately but, after personal intervention by Churchill, in December 1941 Mosley and two other 18B husbands were permitted to join their wives at Holloway. After more than three years' imprisonment, they were both released in November 1943 on the grounds of Mosley's ill health; they were placed under house arrest until the end of the war and were denied passports until 1949.
After the war ended, the couple kept homes in Ireland, with apartments in London and Paris. Their recently renovated Clonfert home, a former Bishop's palace, burned down in an accidental fire. Following this, they moved to a home near Fermoy, County Cork, later settling permanently in France, at the Temple de la Gloire, a Palladian temple in Orsay, southwest of Paris, in 1950. They were neighbours of Duke and Duchess of Windsor, who lived in the neighbouring town Gif-sur-Yvette, and soon became close friends with them.
Once again they were well known for entertaining, but were barred from all functions at the British Embassy. During their time in France, the Mosleys quietly went through another marriage ceremony; Hitler had safeguarded their original marriage licence, and it was never found after the war. During this period, Mosley was unfaithful to Diana, but she found for the most part that she was able to learn to keep herself from getting too upset regarding his adulterous habits.
Diana was also a lifelong supporter of the British Union of Fascists (BUF), and its postwar successor the Union Movement, to which she made financial contributions until the 1994 death of its organiser Jeffrey Hamm.