I Do, I Do

Both of Lee Jang-woo, and Yoo Ah-in wants to become a top fashion designer. . but starts out as a vendor. Soon enough they accomplish their goals.

Both are about women that have one night stands that end up in pregnancy.

In both the female lead thinks about more of her job than a relationship. They would do anything to get what they want. But they meet a guy, younger than them, that at first they just use him but later fall in love. They face difficult situations because of the age difference.

Both series deal with an accidental one night stand which results in the female lead accidentally getting pregnant. However in one series it is the female who is the rich director of a company and the male the poor spinster(I do I do) and in the other it is the exact opposite.

Both stories about women who face the dilemma & potential consequences of motherhood as a single un-wed parent. I do, I do (2012) is much more recent than Virgin Road (1997), however it is uncanny how there is very little difference in societal reactions & expectations from then & now

Surprised nobody has recommended this one already but here it comes...
In both dramas the female lead works in fashion field, one is a shoe designer and the other a magazine editor. In Bad Couple the woman wants a baby because it's going to be her last chance soon to have a child but she doesn't want a husband just like the woman in I Do, I Do who gets pregnant after one night stand. Both women are suffering health problems during pregnancy and in both the baby's father is younger.

Career couple finds love and humor along the way.

Both dramas feature strong independent women who have one night stands with younger men. The male characters have to prove themselves to stubborn women (who are really just insecure about needing someone to love).

Two great shows which stray from the typical cliched drama plots.

Both set on fashion and designing. A cute tale of romance and survival in the fashion world.

A bitchy business woman has physical contact with a younger man (kind of one night stand). Unfortunely they meet again at her work place. She don't even recognise how she changes, become softer and slowly fall for the kind young guy.

Orihara Yuka is an artist with savant syndrome, closely protected by her mother and her cousin. When one of her works is entered into a competition and wins first place, she is thrust out into a much wider world. She meets Sawatari Toru, a bitter reporter with a hard past, who treats her as if she were normal.

Seven years ago, top star Kanzaki Ren and college student Moriyama Suzu spent a night together at a hotel. Shortly afterward, Suzu secretly became pregnant with Ren’s child. Since then, she has raised their son, Yu, on her own, working hard to make a living as a single mother.

One day, Yu is seriously injured in an accident and requires expensive medical treatment. Driven into a difficult financial situation, Suzu unexpectedly finds work at Kanzaki Productions, the company headed by Ren himself. Their reunion after seven years sets their fates in motion once again. The existence of Yu, secrets hidden within the Kanzaki family, and Suzu’s own surprising origins gradually come to light.

As truth after truth and conspiracy after conspiracy is revealed, Suzu finds herself drawn into a series of trials and challenges. Can she and Ren overcome the many obstacles before them and ultimately find true love together?

Both drama has
- Older Woman/Younger man
- Office setup
- Boss/employee, superior/subordinate relationship

They both are about powerful women who are experiencing unplanned pregnancies and are keeping the baby and trying to navigate their life with their new family.

Both start with a one-night stand which leads to a pregnancy. The characters connect only after that event.