Set during the Joseon Dynasty, the story of the meeting between the young widow Jung Soon-deok and young widower Shim Jung-woo as well as the struggle the two go through together to marry off the four young maidens who represent Joseon.
Jung-woo, who won first place in the state examination, believed that all he had left was to begin his official career. However, he captured princess’s attention, ultimately leading to him becoming the the son-in-law of the king. To make matters worse, on the day of their wedding, the princess collapses and he becomes a widower at a young age. Soon-deok is officially the second daughter-in-law of the family of the first vice-premier, but she is secretly leading a double life as the best matchmaker in Hanyang for a simple reason. Bringing people together with their loved ones fills her with excitement and happiness. A young widow and a young son-in-law of the king meet to obey the royal command to solve the issue about old maids and old bachelors! Will they lead the matchmaking project to success and make their second love work out?