Hi, so I know this sounds a little bit weird, but can you recommend me asian dramas with the male main lead being unexperienced and a female main lead that has been in a relationship already?

Ive watched Im not a robot already and really enjoyed it. Im kinda sick of seeing this Badboy-Innocent girl scheme after watching over 50 dramas...

Definitely try Jdramas: Takane No Hana, we married as a job and Densha otoko

Or maybe kdramas: That Fool  and Smile You

Although in the first two, I'm not sure they ever specified whether the female lead has ever really been in a serious relationship, either.  But for sure the female lead has more dating experience than the male in all three of these.

Inexperienced ML:

  • The Eternal Love - as part of their constant back-and-forth bickering and teasing, the ML offers a deal (he'll give the FL papers for a divorce if she satisfies him in bed) that he doesn't actually expect the FL to take him up on, but to his surprise she agrees and kisses him first for once and then sleeps with him; although the ML has two concubines, he avoids them almost entirely (partly because he knows they're spies); it's later confirmed that the ML is a virgin before sleeping with the FL, and confirmed that the ML takes the FL's first kiss (so she presumably also has never been in a relationship before, although she definitely doesn't have a shy personality)
  • 100 Days My Prince - confirmed that the ML and FL have only ever loved each other; the ML's refusal to marry leads to rumours that he's gay
  • Thirty But Seventeen - confirmed that the ML and FL have only ever loved each other; the ML has self-isolated since he was young due to a traumatic event in his childhood; the FL is also inexperienced as she was in an accident that put her in a coma for over a decade
  • Queen In Hyun's Man - (I can't remember if it's confirmed that the ML is inexperienced, but it's at least implied and he's used to a very traditional approach to male/female interactions); the ML is from ancient times and the FL is an actress in modern times; the FL's ex-boyfriend plays a small role in the story and the FL kisses the ML first
  • You Who Came from the Stars - ML is several-hundred-years-old alien; similar to I'm Not a Robot, sharing DNA with humans (e.g. by sharing a meal or kissing) causes a strong reaction kind of like putting him in a coma, so he avoids sharing meals and hasn't been in a relationship; the FL kisses the ML first while she is half asleep and drunk iirc
  • What's Wrong With Secretary Kim - similar to I'm Not a Robot, a traumatic event in the ML's childhood resulted in him avoiding the touch of most women (but not the FL) and certain things, including zip ties (in an innocent way) and kissing, trigger panic attacks / a subconscious defence reaction
  • Healer - the ML lives cut off from society and barely interacts with anyone except when he's running a mission as a man-for-hire; the ML kisses the FL first but he's very gentle and her eyes are covered at the time; the director told JCW to tone-down his acting because it was the character's first kiss and he shouldn't look too experienced; the FL takes the lead during their second kiss, which leads to them sleeping together; after the ML and FL sleep together, the ML is extremely clingy (in a cute way) while the FL isn't clingy at all

Currently airing:

  • Feel Good to Die | ML has never dated before and it shows lol. 
  • Mama Fairy and the Woodcutter | confirmed ML and the 2ML has never dated anyone before. Whereas the FL has lived for 699 years and has been married before (and she's searching for her reincarnated husband). 

Finished:

  • Are you Human too? | ML is an android so not sure if that counts. 
  • Black | ML is a reaper trapped in the body of a detective so he has never dated before. FL was confirmed to have had at least one ex-bf at the start of the series. 
  • Where the Stars Land | I believe both leads and the second couple have never dated before. Though it's only confirmed for the ML. 
  • Bring it on, Ghost | ML has never dated before.
  • Chicago Typewriter | ML has little dating experience. 
  • Come and Hug Me | leads have never dated anyone else before and they have love each other since they were kids. 
  • Cruel City | ML has never dated before, but the romance is a small part of the story. 
  • Kill me Heal me