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In the Joseon era (1392-1910), the young widow Jung Soon-deok has lived an eventful life. She married into a powerful family, but has since lost her husband. She lives a double life, going under an alias when she acts as a matchmaker, pairing up eligible bachelors with suitable brides. Shim Jung-woo, meanwhile, is the King’s unhappy son-in-law. His chagrin derives from the fact that his bride, the princess, died just moments after he tied the knot with her. — But while Shim Jung-woo is a very grumpy individual, he is also one of the smartest men in the land – and became the youngest person ever to pass the Civil Service Exam. This unlikely duo must team up to find husbands for a handful of important Joseon women whose age is starting to creep up. Their outlooks on life are very different, but they have no choice but to work together. Could playing Cupid for others put them back on the path to love?