The Matchmakers

both the matchmakers and flower crew: joseon marriage agency center on people who dedicate their time to finding the right partners and arranging proper marriages back in the joseon era. they handle strict customs and tough situations to bring people together and create happy unions while working through all sorts of unexpected twists and challenges along the way.

Both are historical dramas in which the leads work as matchmakers but initially can't or won't find love themselves.

Both dramas are 'fun' ancient costume drama where the couple are on an equal footing in smarts and personality. Fun is in quotes because the underlying basis of the story is tragic/sad but it paves the way for the couple to connect and find new happiness.
Oddly I kept thinking of The Red Sleeve when watching this as well and was happy each of these dramas ended happily vs. Red Sleeve.

Both stories are set in the great Joseon dynasty (1392-1897) which focuses heavily on moral virtues of people. Both stories also tell story about matchmaking business – how it began, the lovestories, the struggles of the business and also the comedy relief of it. Both stories also have romantic sideline story which does add to the ‘’matchmaking magic’’.

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.

Male lead has inherent skills is matching up two people romantically. Both main leads seem to have a fate of living lonely lives but defy it through sincere love.

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.