Chiang had a love life worthy of an emperor. He had three wives, one concubine and many lovers, though fewer than Mao Zedong .
In one diary entry, ahead of a trip to Hong Kong, he wrote that the ladies there were young and beautiful and he must resist them. But, after his return, he wrote that he could not restrain himself and criticised himself, saying that he must change this bad habit.
His first marriage was in 1901, when he was 14; it was arranged by his family to Mao Fumei, the daughter of a rich local family in his hometown of Xikou, Zhejiang province. She was 19 and illiterate and had bound feet - considered virtues at that time. Their son, Chiang Ching-kuo, was born in 1910.
Chiang found the gap with his wife was too large, and the relationship deteriorated. In 1913, he brought back from Shanghai Yao Yecheng, who had worked in a high-class brothel in the city. Mao accepted Yao as her husband's concubine.
In 1919, Chiang adopted the three-year-old son of a friend, named him Chiang Wei-kuo and gave him to Yao to raise. Initially they got along well, but he complained of her incessant gambling and paying too little attention to him.
In Shanghai in 1919, he found a new girlfriend, Chen Jieru, the daughter of a rich businessman 19 years his junior. They married at the end of 1921 and she threw herself into his revolutionary life. She could not have children, so they adopted a daughter and he gave her Wei-kuo to look after. But Chen did not have the connections and money to match Chiang's growing ambitions. In 1926, he decided to marry Soong May-ling, a member of one of the most powerful families of the Republican era.