Jeong-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. Jeong-woo asks Soon-duk for help as she's the best matchmaker in Joseon, but she refuses.

Soon-duk decides to work with Jeong-woo and signs a contract. Hwa-rok, the third of the Maeng sisters, and Soon-duk come up with a way to make the sisters get married. Meanwhile, Jeong-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-duk uses the petitioner’s drum to save Lady Cho and expose Minister Park’s corruption. Soon-duk 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.

Jeong-woo and Soon-duk bring the Maeng sisters to Sunhwa Temple, where they can meet bachelors from all over the country. Soon-duk tirelessly tries to make matches for the sisters and shows off her matchmaking skills. Lady Park, who is bothered by Jeong-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 her and her faction.

Jeong-woo becomes Geun-seok’s tutor, which puts Soon-duk in a pickle as she has to keep hiding her identity. Soon-duk and Jeong-woo finalize the bachelor candidates for the Maeng sisters. Meanwhile, Lady Park finds out that Soon-duk has been going outside without her permission.

Jeong-woo, Soon-duk, and Sam-soon figure out what exactly happened to Lady Cho Ok through Lieutenant Jung. They decide to create a new rumor to drown the old rumor regarding Lady Cho Ok and Ha-na. Meanwhile, the Crown Prince gets abducted by the left state councilor’s men, but Ha-na helps save him.

Soon-duk rescues Jeong-woo from the river. Lieutenant Jung recognizes Soon-duk, his only sister, so Soon-duk asks him to keep it a secret from Jeong-woo. The King finds a way to dismiss the Minister of Defense 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-duk to her late husband. Jeong-woo confesses his feelings to Soon-duk, but Soon-duk 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 Jeong-woo look into the case to help her.

Soon-duk and Jeong-woo meet Socheon, 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 Jeong-woo and Soon-duk picked.