I've searched a lot and somehow I find it rather difficult to find a drama, that comes close to what I want. 

What I want is a drama, where the FL is friends with a playboy. Either they become friends or, what I would personally like more, they are childhood friends. 

Important is, that they don't really see each other as love interests. Like, the ML has had a lot of girlfriends or just flirts all the time but just doesn't see the FL as an option (Maybe he tried to shoot his shot at the beginning, but that didn't worked out, so he just stayed friends) and the FL just doesn't see him as an love interest, because he is a playboy, or she has a different person she likes, or she never thought of him in that way and so on... 

One of the most important things is, that the ML should definitely fall in love first. I really can't stand playboy series, where the girl falls in love first. And it should take her a while, before she returns his feelings.

The only dramas that come to my mind, that got even close to my description were You Drive Me Crazy (Really short tho and they had a one night stand what I wouldn't like in a longer series) and Plus Nine Boys (Really close. REALLY close, but they did 1 thing I absolutely cannot stand and that's the "She liked him all along but didn't say anything, because she knows he is a player but still liked him secretly all this years" like wtf? No!)

I know it's specific, but there can't be just these 2, right? :((

Country doesn't matter. I also watch Anime, turkish, hindi ... anything in asia is fine xD

 Bubblegum20:
the FL is friends with a playboy

 Bubblegum20:
the FL just doesn't see him as an love interest

 Bubblegum20:
the ML should definitely fall in love first

 Bubblegum20:
they are childhood friends
  • Kiss Scene in Yeonnamdong - The ML doesn't have the asshole / arrogance factor of a playboy, but he goes through many girlfriends / is very experienced with kissing and dating. He and the FL are childhood friends. The ML liked the FL first but it takes a long time for him to fully realize it / admit it to himself. He is afraid of dating the FL because he doesn't want to risk breaking up and drifting apart.
  • Adult Trainee - Episode 3 - 5 only. The ML is not a playboy (despite what the FL assumes, he doesn't have romantic experience and doesn't flirt around), but he is handsome, athletic and has the self confidence of a playboy. He and the FL are childhood friends. It's revealed later on that the ML liked the FL first.
 Bubblegum20:
they become friends
  • Before We Get Married - The ML is pretty much an asshole and a playboy at first. He pursues the FL aggressively and is rejected. When he realizes his feelings are serious, he changes his approach, but still gets rejected. The FL insists that they can only be "friends", but it's definitely not a conventional friendship.
  • What's Wrong with Secretary Kim - "Friends" might not be the most accurate word for their relationship, especially at the beginning of the drama (as the title implies, the FL is the ML's secretary), but they've known each other for years and the FL does not consider the ML to be a possible romantic partner. The ML has the narcissistic factor of a playboy, but iirc not much in the way of actual relationship experience.
  • To Fly With You - The ML is not a mega playboy, but he's athletic, handsome, confident and sought after. The ML and FL become begrudging allies before they become friends.
  • Accidentally in Love - The ML is not a playboy, but he's a handsome and popular idol. The ML and FL become frenemies / begrudging allies before they become friends.
  • Ugly Duckling Series: Perfect Match  - I can't remember enough about the ML to say definitively whether or not he's a playboy, but I remember he was handsome, confident and flirtatious but poor (major spoiler - except that the poor part was fake - he was actually rich but didn't want people to get close to him because of it). Also, iirc, one of the reasons the FL doesn't consider the ML to be a possible romantic partner is that she feels that she is too ugly to be with someone handsome.

Five Chlldren - family drama with multiple leads. A quiet elementary school teacher forms an odd friendship with a professional golfer/model while she is getting over a long-time crush (she's never had a real boyfriend). She doesn't even recognize when he starts becoming attracted to her.

 AH :
Kiss Scene in Yeonnamdong - The ML doesn't have the asshole / arrogance factor of a playboy, but he goes through many girlfriends / is very experienced with kissing and dating. He and the FL are childhood friends. The ML liked the FL first but it takes a long time for him to fully realize it / admit it to himself. He is afraid of dating the FL because he doesn't want to risk breaking up and drifting apart.

Thank you! 

Uhm... I personally despise Before we get married a lot  xD It's the only drama with the Playful Kiss series that I dropped. I hated the mood, I hated the story, I hated the characters. I basically hated everything, so that's really not my cup of tea. 

What's wrong with secretary kim I've watched and I liked it, but it's not the dynamics I am looking for. 

Accidentally in love comes a bit close, even tho he is not a player, but I loved the dynamics in this one. You could really see, that they were friends before they fell in love. 

Otherwise Kiss scene in Yeonnamdong sounds exactly like what I wanted, thank you so much^^ I will watch the other ones as well :)

 maidenholmes:

Five Chlldren - family drama with multiple leads. A quiet elementary school teacher forms an odd friendship with a professional golfer/model while she is getting over a long-time crush (she's never had a real boyfriend). She doesn't even recognize when he starts becoming attracted to her.

Thank you^^

 Bubblegum20:
Otherwise Kiss scene in Yeonnamdong sounds exactly like what I wanted, thank you so much^^ I will watch the other ones as well :)

You're welcome. Hope you enjoy them!

Wow when I read you're description I thought guaranteed I'd know something...but actually thinking back, it's actually difficult to find something. Here are some not-perfect matches.

Something Just Like This (2020) is not a perfect match. They are childhood friends (almost siblings) that slowly feel for each other. ML is first to fall. But he's flirty but not exactly a playboy.

Don't Mess With Girls (2021) ML is playboy, becomes friends with FL due to their circumstance (fantasy element). I think ML falls for FL. But there's no eng sub when I watched it.

Why Women Love (2022) ML is playboy, becomes friends/subordinate to FL and falls for FL kinda early on but it wasn't love at first sight.

Sweet Teeth (2021) SIDE CP: male is playboy, female has had a few boyfriends (but always gets brokenhearted). They are longtime friends (male is brother of FL and female is best friend of FL). They slowly get together, male likes female first.

Ex-Girlfriend Club (2015) It's been a while since I watched this and it's not an exact match. But the ML and FL had a "thing" in college...like they we're for sure friends but only thinking back on it the FL realizes they were possibly in a relationship. ML had a blurry understanding as well. But ML has had many relationships since then and he publishes comics about it. In the present day, they are long-lost friends and FL first kind of likes ML but then ML very obviously falls for FL when she's kind of over him. And ML realizes that he's liked FL all along.

 elie808:
Wow when I read you're description I thought guaranteed I'd know something...but actually thinking back, it's actually difficult to find something. Here are some not-perfect matches.

Something Just Like This (2020) is not a perfect match. They are childhood friends (almost siblings) that slowly feel for each other. ML is first to fall. But he's flirty but not exactly a playboy.

Thank you so much!^^ From your descriptions, all of those dramas sorta sound like what I want. 

But yeah, I always have relatively specific requests, so it is kinda hard for me to find somethings, that fits my taste^^" :D