[2] Dong has been described as the famous courtesan of her time, known for her beauty and talent in singing, acting,[3] needlework and the tea ceremony.

[4] Similar to other courtesans of the late Ming Dynasty, Dong's moral qualities were emphasised among her admirers more than her talents.

The other famed courtesans of this group are Ma Xianglan, Bian Yujing (卞玉京), Li Xiangjun, Liu Rushi, Gu Mei, Kou Baimen (寇白門), and Chen Yuanyuan.

Dong Xiaowan was regarded as a treasure by her parents, who carefully taught her poetry, calligraphy, painting, needlework.

However, the shop assistant played tricks and owed thousands of taels of silver.Lady Bai fell ill, so the fifteen-year-old Dong Xiaowan had to find a way to repay the family debt and raise medical expenses for her mother.

[9] After Dong Xiaowan became a courtesan, she popular peoples because of her intelligence, beauty, excellent calligraphy and painting, and knowledge of recipes and tea ceremony.

[10] Dong Xiaowan, who was proficient in music, also co-starred with Gu Hengbo, who played a young man, in "The Story of the Western Tower(西楼记)" and "Teach Son(教子)".

Mao Bijiang's "Recalling Words(忆语)" wrote that Xiaowan was tired of the hustle and bustle of Qinhuai and chose to move to Bantang.

[15][citation needed]Qian Qianyi once accepted Dong Xiaowan as his apprentice, and took her to live in Huangshan with Liu Rushi, where she learned poetry and painting and achieved remarkable results.

Her mother had been dead for two weeks and Dong was quite ill. She proposed that she become his concubine and, refusing to take no for an answer, allegedly followed him for 27 days on his boat.

In order to facilitate Dong's marriage, Qian Qianyi, husband of fellow courtesan Liu Rushi, paid off her debts of 3,000 gold taels and had her name struck from the musicians' register.

Soon after, the household moved to Zhejiang, where Dong compiled a book titled Liuyan ji (Chinese: 流宴集) about jewellery, women's costumes, pavilions and parties.

Dong Xiaowan hugged her husband every night, let him lean on her to sleep, and she slept sitting up for a full 100 days.

Her works include "Colorful Butterflies", "Lonely Mountain Feeling of Passing Away", "Ladies", "Autumn Garden Elegance", "Imitation of the Brushwork of Mr. Liuru", "Orchid Scroll" etc.

[31] Dong Xiaowan also made a kind of crispy candy with fine white sugar, shelled sesame, pure maltose and other flour, and asked someone to bring it from Qinhuai to Mao Bijiang to express her deep affection.

In contrast, he downplayed her painting abilities, which Jean Wetzel has suggested may have been an attempt to disassociate Dong from her previous life as a courtesan.