Jeong-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-duk, a skilled matchmaker, and falls for her. Meanwhile, the King wants to issue a Marriage Ban, only to be met with opposition.

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.

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. Jeong-woo proposes to Soon-duk, and he even gives her a noble status. However, Soon-duk reveals that she is a noblewoman with a son. Meanwhile, Lady Park finds out what happened to her late eldest son.

Soon-duk and Jeong-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-duk decides to come clean and confesses to her mother-in-law that she is the Lady Yeoju who has been working with Jeong-woo. Meanwhile, Jeong-woo finds out which family Soon-duk belongs to.

The King arrests Jo Young-bae and Park Bok-ki and accuses them of treason. The court maid of Dongungjeon who lost her consciousness finally wakes up. Jeong-woo is put in a position where he has to help Lady Park and her family, so Soon-duk wouldn’t be hurt. Meanwhile, Lady Park comes up with a plan to save Prince Jinsung and the family.

Jeong-woo tells Soon-duk 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 Jeong-woo’s marriage to the late Princess so he could help with national affairs. Meanwhile, Soon-duk 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. Soon-duk 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 Minister of Defense falls through and blames Soon-duk for it. She pulls a trick and accuses Jeong-woo of violating Soon-duk. The King is left with no choice but to punish Jeong-woo with poison. Lady Park tells Soon-duk to take her own life for disgracing her family.