Bruce Lee's Martial Arts Master Ip Man Had A Tragic Romantic Past

Ip Man was a martial arts master, per Google Arts and Culture, and his claim to fame was that he taught Bruce Lee to fight. Before Bruce Lee was starring in kung fu movie classics like "Fists of Fury" and "Enter the Dragon," he was training under Ip Man, starting with his first class in 1953. Throughout his life, Ip Man taught hundreds of students to perfect their martial arts techniques. But despite his successful career, his personal life wasn't always easy — he and his wife had rough periods in their life that tore their family apart.

According to Biography, Ip Man grew up in Foshan, China, with his parents and three siblings. His family was fairly wealthy, so Ip Man was able to pursue his passions as he grew up. He mostly loved Wing Chun, a 300-year-old martial art, which he studied from a young age and later began teaching. 

Ip Man met a woman named Cheung Wing-Sing, and the two got married. Cheung Wing-Sing grew up in Foshan, China as well, per The Cinemaholic. They had two sons, Ip Chun and Ip Ching, and two daughters, Yip Ar Sum and Yip Ar Woon (per Biography).

According to Black Belt Magazine, Ip Man's comfy life was interrupted in 1937 when he was forced to join the army as China fought Japan. For the next four years, Ip Man was away from his family, which took a heavy toll on all of them.

Cheung Wing-Sing got sick while he was away. Ip Man owned a house and a farm, and the farm suffered when he wasn't there to care for it. He had grown up wealthy, but now found himself quite poor as the war went on. 

Around 1949, the Communist party won the war — and that was bad news for Ip Man and his kids. Taking only his most valuable possessions, he and his sons split up. Ip Man headed for Hong Kong, while his sons, who were now grown up, went to Foshan.

This was a difficult period for the martial arts master, per Black Belt Magazine. He was reportedly so depressed over this downturn in his life that he was briefly homeless. A few people saw him wandering around aimlessly and helped him find a job at the Restaurant Worker's Union Hall,and soon, he was back to teaching his very popular Wing Chun classes.

Per The Cinemaholic, since Ip Man and his wife separated, they never saw each other again after 1951. She and one of their daughters stayed in Foshan, while he remained in Hong Kong. Cheung Wing-Sing died of cancer in 1960.

Per Black Belt Magazine, Ip Man did find love again — he remarried in 1954 to a woman who was about 16 years his junior. Ip Man reportedly had a mistress, too, reports The Cinemaholic. Since she was from Shanghai, she gained the nickname "Shanghai Po." Not only did she and Ip Man date, starting around 1955, but they also had a child together, named Ip Siu-wah. 

Along with Ip Man's other two sons, Ip Siu-wah studied martial arts with his dad. That's because Ip Man was actually able to reunite with some of his family and extract his two sons from China, reports Black Belt Magazine. He spent the final decades of his life teaching martial arts with his family by his side.