Lovely Sister (2022)

Very similar storyline with an older boss lady who wants to marry a younger, gentle guy. Many other parts of the story are also the same, though many also different. Destined to Meet You is a minidrama and in the beginning more absurd, but also very funny.

It's almost similar except for the fact that it is short nd that is long contract marriage love childhood trauma love and pevery thing

On both dramas female lead is strong, career driven CEOs, both goes into contact marriage, on begin again female lead breaks up from the male lead & gives birth secretly

Also, an age gap drama where the female lead is older and the male lead is younger. One is a short length drama while the other is a full length.

Main characters meet in a bar. Contract marriage. Main character's families are rivals. Quick marriage froth with uncertainty. ML refusing to divorce. Strong FL vs. thoughtful ML.

Both are dramas with a contract marriage between the main couple.
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Both are a contract marriage story in which the two unexpectedly have a past connection. Both pairings have great chemistry. The same actor is the ML of DTMY and the SML of TTFIL.

- Both dramas have a sassy female CEO and a younger/seemingly younger male lead
-In both, the FL is driven by career and money and the ML is more emotionally engaged

Both are short length dramas about a love story between an older office working FL and a younger ML.

A modern-setting romance by the same writer/director team as Butterflied Lover, Provoked, A Familiar Stranger, and The Killer is Also Romantic.

Both are short dramas with an age gap between the leads, and past trauma that an adopted or step brother is responsible for.

Both are mini dramas with a strong-willed, determined CEO FL who chases the ML who is un-interested at the beginning. Both dramas have a similar relationship and interactions between the main couple.

Both are mini dramas with a contract marriage between the leads.
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Both are age gap romances (older FL and younger ML) who are connected due to a traumatic event on the day they met years before. In both dramas, the one responsible continues to be in their lives in the present day when they meet again.