Sim Jung Woo is an intelligent and handsome young man. He was the youngest to place first in the state examination, but he was picked to become the princess' husband. During their wedding ceremony, the princess suddenly died. Sim Jung Woo's life changed and he became the most unfortunate man. According to the Joseon period custom, he is not able to take the government post and he can't remarry. He then becomes involved with Jung Soon Deok. Jung Soon Deok is a widow whose late husband was the second son of the first vice-premier. She secretly leads another life under the pseudonym of Yeo Joo Daek. As Yeo Joo Daek, she works as a matchmaker and also peddler of women's items like cosmetics and accessories. She is the best matchmaker in the capital city of Hanyang. Sim Jung Woo and Jung Soon Deok become involved with each other and they try to get older single men and women to marry as matchmakers.