Rich Man, Poor Woman (2012)

29-year-old Hyuga Toru is a wealthy man. He first started to run an internet website from his small room and his hobby began to make a lot of money. Nowadays, he doesn't like to socialize and if somebody comes to him he suspects that they may want his money. Sawaki Chihiro attends a job fair and by an unexpected occurrence begins to work for Toru. Chihiro soon realizes that Toru isn't so bad. There's pureness in him and also a good deal of loneliness. She then begins to have feelings for him

Both stories involve an older woman falling in love with a younger man. I would consider both to be an almost slice of life romance. There is no "villainous" parents or such attempting to keep the two would be lovers apart. Nor are there any situations too far out there to be realistic. The stories are gentle and involve the differences in ages when it comes to perspectives on relationships. Also, both are adaptations of a manga.

Ishihara Satomi plays the main female role in both dramas. the plots are quite different, but if you enjoyed the chemistry between Yamapi and Ishihara, you will enjoy the chemistry between her and Oguri Shun.

Similar triangle love story. First FL like SML than as time goes by she attract to ML. They all live in the same apartment building. Both of the leads not get along very well but slowly changes & they realized that they are in love with each other.

Another office romance drama about a younger FL who always leaves at the end of the regular working day and never works overtime. She tries to be as efficient as possible and productive during her normal working hours. She broke off her engagement with older ML coz he is workaholic.

Similar triangle love story. First FL like SML than as time goes by she attract to ML. They all live in the same apartment building. Both of the leads not get along very well but slowly changes & they realized that they are in love with each other.

A guy creates an app, a girl in the office becomes his friend and then his girlfriend, before he realises that someone close to him has betrayed him......can he recover and learn from the betrayal?

In reality I think Entrepreneurial Age is actually a Chinese version of Japan's Rich Man, Poor Woman.

Narukawa Sana is a young CEO who founded the startup "Dream Pony" that deals with educational apps when she was 23. Although reckless, Narukawa has a goal and that is to make "Dream Pony" into a unicorn company and that its business is available to everyone all over the world within 10 years. The company did well when it was first launched but Narukawa became frustrated as there hasn't been any huge growth. Narukawa dedicates her time mostly on her work and has been neglecting her private life and romance. One day, a middle-aged salaryman Kotori Satoshi decides to change his job and starts working at "Dream Pony". At first, Narukawa is not fond of Kotori but the two become closer as Kotori helps Narukawa by giving advices based on his experiences. Meanwhile, Narukawa's co-founder Suzaki Ko has been in love with Narukawa but he is unable to suppress his feelings after the arrival of Kotori. The team now gets caught in a triangle between work and love.

Izumi Hidaka is 36-years-old and the CEO of start-up game company Pegasus Ink. Four years ago, she developed the game Love My Pegasus, which was targeted towards women and became very popular. Since then, she has been obsessed with the character Kento-sama from Love My Pegasus. One evening, Wataru Igarashi suddenly appears in front of drunken Izumi Hidaka. She is shocked by Wataru Igarashi’s appearance, which is just like her game character Kento-sama. Wataru Igarashi is a 23-years-old man. But, Izumi Hidaka is disappointed with Wataru Igarashi. Except for his physical appearance, Wataru Igarashi is the opposite of her well-mannered, cultured, and vivacious game character Kento-sama.

Both dramas about a big boss and his emploee.
The boss is also rich and hides his emotions.

Office romance comedy about a older ML who is always going back home on time after office hours & doesn't like to do overtime work in the office & a younger FL who is working overtime after office hours & her nickname is sachiku aka office slaves. This two people met & start their up-downs relationship but they kept their relationship hidden in the office.

Izumi Hidaka is 36-years-old and the CEO of start-up game company Pegasus Ink. Four years ago, she developed the game Love My Pegasus, which was targeted towards women and became very popular. Since then, she has been obsessed with the character Kento-sama from Love My Pegasus. One evening, Wataru Igarashi suddenly appears in front of drunken Izumi Hidaka. She is shocked by Wataru Igarashi’s appearance, which is just like her game character Kento-sama. Wataru Igarashi is a 23-years-old man. But, Izumi Hidaka is disappointed with Wataru Igarashi. Except for his physical appearance, Wataru Igarashi is the opposite of her well-mannered, cultured, and vivacious game character Kento-sama.

29-year-old Hyuga Toru is a wealthy man. He first started to run an internet website from his small room and his hobby began to make a lot of money. Nowadays, he doesn't like to socialize and if somebody comes to him he suspects that they may want his money. Sawaki Chihiro attends a job fair and by an unexpected occurrence begins to work for Toru. Chihiro soon realizes that Toru isn't so bad. There's pureness in him and also a good deal of loneliness. She then begins to have feelings for him.

29-year-old Hyuga Toru is a wealthy man. He first started to run an internet website from his small room and his hobby began to make a lot of money. Nowadays, he doesn't like to socialize and if somebody comes to him he suspects that they may want his money. Sawaki Chihiro attends a job fair and by an unexpected occurrence begins to work for Toru. Chihiro soon realizes that Toru isn't so bad. There's pureness in him and also a good deal of loneliness. She then begins to have feelings for him

Both stories are about a rich man and a poor woman and how it is possible to have a romance even dispite the financially gap.