See You in My 19th Life

Both have similar vibes in music and eerieness.
Both have peculiar female lead
Both have romance genre

Both are interesting and captivating dramas, they have a common plot in which the protagonist is an immortal being who remembers their past lives, they begin to surround themselves with people who have been an important part of their previous lives and seek to heal those wounds that they have left open. Both dramas feature great actors and actresses, have an amazing OST and a plot that will grab you from the start.

The story about Ban Ji Eum has the ability to remember all her past lives, living through countless reincarnations for nearly a thousand years. After a tragic accident ends her previous life, she seeks to reconnect with the people from that life, focusing on Moon Seo Ha, whom she met in her 18th life. As she navigates her 19th life, will memories of her past hinder her romance, or can love endure across lifetimes?

In both dramas the leads (and more characters) are connected by a past life. In Extraordinary You it's a "story" but it still counts as a past life since for the characters it was their life. In both cases it's revelead in later episodes that this other life exists and what happened in there and how it connects the leads and the other characters.
Also *spoiler* in both cases the FL forgets about the ML towards the end but the ML remains by her side anyway, trying to make her remember they were in love.

Reincarnation, meeting past lover again.

One of the characters doesn't know that his/her past lover has been reincarnated.
Both still harbor feelings towards each other.

-Both are supernatural romances with one person living for hundred of years and the other being a high powered CEO and heir to a fortune.
-Murder plot mystery
-Opposing personailty secondary couple including a secretary
-Traumatic past lives
-Call backs to Korean culture and history
-Lost memories of first life
-Mysterious person who knows more than let on about the supernatural
-Strong female characters

Although they've got very different premises, if you're into dramas where the main couple are absolutely destined for each other by the stars then you can give this show a go. The leads in this show go through time and all laws of physics to be with each other, somewhat like how Jieum dedicates a whole life and a half to finding and being with Seoha. ATCY has romcom aspects somewhere in the middle of the show, but the emotional turmoil definitely trumps it all. Be warned.

Both dramas tell moving love stories with reincarnation as a major plot device. See You in My 19th Life focuses more on a love story between two people. Chicago Typewriter tells the story of three protagonists whose past lives are part of a historical era that marked the entire country. But both dramas explore the kinds of emotions, bonds, and actions that leave marks too powerful to erase.

Both drama is fantasy romcom and both remind me of each other maybe bcus of the characters, FL is weird in both drama and really hitting on the ML in the hard way LOL also with the ML who look clueless/innocent but actually really courageous..

Both are dramas that carry themes of reincarnation, childhood friendship, love & death............................

Fantasy romance core
Both dramas hinge on extraordinary circumstances that test whether love can transcend time.
Dual timelines / past influencing present

Rom-com start, heavier turn later
Midway, they shift into frustration, tragedy, or suspense, showing the cost of destiny.

Themes of fate and inevitability
Characters wrestle with whether love is pre-ordained or a choice.

Both dramas ask: Can love survive across lifetimes or centuries?

Both shows feature timeslips events and both leads are looking forward to connecting with people in past years in order to change their fate.

Both have a similar fairytale like feel for the first half. Both have scheming rich families, a ML who begins the drama by losing his mother and in the present day storyline has trauma as a result of his childhood, and a magical, flirty, and eccentric FL.

Both the leads reconnect with the people relevant to his life, in his two different stages in life. Both dramas have a slice-of-life vibe to it.

Both of the are written by Lee Hey, so I recommend that you could watch the other addaptions that is coming