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.
Jung Woo has been living as a widower and in celibacy for eight years after his wife, a princess, died during the wedding. He writes appeals to annul his marriage with the princess, but they never go through. One day, he runs into Soon Deok, a skilled matchmaker, and falls for her. Meanwhile, the King wants to issue a Marriage Ban, only to be met with opposition.
Jung Woo suggests a way to marry off the crown prince. The King gives him a mission to marry off the three spinsters of Mount Nam Valley, assuring him that the appeal he submitted will be reviewed positively. Jung Woo asks Soon Deok for help as she's the best matchmaker in Joseon, but she refuses.
Soon Deok decides to work with Jung Woo and signs a contract. Hwa Rok, the third of the Maeng sisters, and Soon Deok come up with a way to make the sisters get married. Meanwhile, Jung Woo procures the golden silkworm poison to figure out if the princess was poisoned to death eight years ago.
The Maeng sisters' mother, Lady Cho, gets arrested for not marrying her daughters off. Soon Deok uses the petitioner's drum to save Lady Cho and expose Minister Park's corruption. Soon Deok comes up with a plan to marry off the three daughters. Meanwhile, the crown prince leaves the palace on Buddha's birthday, and his opposing force makes a move to get rid of him.
Jung Woo and Soon Deok bring the Maeng sisters to Sunhwa Temple, where they can meet bachelors from all over the country. Soon Deok tirelessly tries to make matches for the sisters and shows off her matchmaking skills. Lady Park, who is bothered by Jung Woo and his recent mission from the King, decides to make him Geun Seok's tutor to figure out if he's someone she can work with and her faction.
Jung Woo becomes Geun Seok's tutor, which puts Soon Deok in a pickle as she has to keep hiding her identity. Soon Deok and Jung Woo finalize the bachelor candidates for the Maeng sisters. Meanwhile, Lady Park finds out that Soon Deok has been going outside without her permission.
Jung Woo, Soon Deok, and Sam Soon figure out what exactly happened to Lady Cho Ok through Lieutenant Jung. They decide to create a new rumour to drown the old rumour regarding Lady Cho Ok and Ha Na. Meanwhile, the Crown Prince gets abducted by the left state councillor's men, but Ha Na helps save him.
Soon Deok rescues Jung Woo from the river. Lieutenant Jung recognizes Soon Deok, his only sister, so Soon Deok asks him to keep it a secret from Jung Woo. The King finds a way to dismiss the Minister of Defence thanks to the Crown Prince. Meanwhile, a slave hunter goes around looking for Lady Yeoju.
The mother of Maeng sisters turns out to be the Agent of Love who introduced Soon Deok to her late husband. Jung Woo confesses his feelings to Soon Deok, but Soon Deok doesn't accept them and tells him to forget about her. Meanwhile, Lady Yeoju gets falsely accused of the murder of Jo In Hyun eight years ago, so Lieutenant Jung and Jung Woo look into the case to help her.
Soon Deok and Jung Woo meet So Cheon, the monk who wrote "The Scholar's Man." They find out that the story was based on what happened to Socheon and Jo In Hyun, and that the two were in love. Meanwhile, the May Festival is held, but the Maeng sisters do not end up with the bachelors that Jung Woo and Soon Deok picked.
The Crown Prince comes to the May Festival to meet Ha Na, but he gets abducted. Upon witnessing the abduction, Ha Na follows them and saves the Crown Prince. Jung Woo proposes to Soon Deok, and he even gives her a noble status. However, Soon Deok reveals that she is a noblewoman with a son. Meanwhile, Lady Park finds out what happened to her late eldest son.
Soon Deok and Jung Woo find a new match for Doo Ri, bringing their matchmaking project to a near end. The King starts an investigation on the interpreter from Ming who procured poison that killed the Princess. Soon Deok decides to come clean and confesses to her mother-in-law that she is Lady Yeoju who has been working with Jung Woo. Meanwhile, Jung Woo finds out which family Soon Deok belongs to.
The King arrests Jo Young Bae and Park Bok Ki and accuses them of treason. The court maid of Dongungjeon who lost consciousness finally wakes up. Jung Woo is put in a position where he has to help Lady Park and her family, so Soon Deok wouldn't be hurt. Meanwhile, Lady Park comes up with a plan to save Prince Jin Sung and the family.
Jung Woo tells Soon Deok that he no longer wants to see her. He does that upon hearing Lady Park tell him that she will do whatever she can to protect her family. The King decides to annul Jung Woo's marriage to the late Princess so he could help with national affairs. Meanwhile, Soon Deok finds out why her mother-in-law wanted to hold Erudite Maeng's daughters' wedding with Ye Jin's at her place.
On the day of the wedding, Ye Jin runs away, which puts Lady Park in a pickle. With the Crown Prince in the house, Lady Park cannot push off the wedding. Sook Deok comes up with a plan to marry off all three couples, only with different matches. However, she keeps encountering unexpected variables.
Lady Park gets furious as Ye Jin's wedding with the son of the Minister of Defence falls through and blames Soon Deok for it. She pulls a trick and accuses Jung Woo of violating Soon Deok. The King is left with no choice but to punish Jung Woo with poison. Lady Park tells Soon Deok to take her own life for disgracing her family.
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