Hey! So I'm a guy, and I like Kdramas. The problem is that so many  kdramas are tailored towards women. You know like the female main character is poor or in trouble, and then the handsome rich nice guy or bad boy comes in and they start a romance.

What I'm looking for is a Kdrama with a Male lead who is poor and humble. And then a rich, beautiful, and successful woman comes into his life and falls in love with him. And I would really like the lead to be likable, so no asshole jerks please. 

Ones I liked that kind of fit this category:

-Angel Eyes

-Innocent man

-That fool

-Ugly Alert

-That winter, the wind blows

Thanks!

Hmm the only I can think that fits your criteria and wasn't mentioned yet is History Of A Salary Man. 

Dal Ja's Spring kind of fits.  Not that's she rich, but she's plenty successful already.

High Society

and

Yong Pal

kinda

Ho goo's love. The female lead is much more successful than the male lead, although not in the "Chaebol" kind of way. I think I never saw a drama reversing so much the typical female and male lead. 

I dont know any drama that fit your criteria, but I will tell you some drama that maybe fit for a guy too.

Descendant The Sun 

A Gentleman's Dignity

Advertising Genius Lee Tae Baek

City Hunter

Drama Special Series Season 3: Sirius

Fight For My Way

Good Doctor

Healer

Hit The Top

Hwarang

IRIS

Jealousy Incarnate

Kill Me, Heal Me

Oh My Geumbi

Oh My Venus

Pinocchio

Please Come Back, Mister

Plus Nine Boys

Poseidon

Pride and Prejudice

Romantic Doctor, Teacher Kim

Shopping King, Louie

Signal

Splash Splash LOVE

Strong Woman Do Bong Soon

The King of Drama

The Legend of the Blue Sea

The Master's Sun

The Producers

The World That They Live In

Tunnel

Weightlifting Fairy Kim Bok Joo

You Who Came from the Stars

I just thinking these drama suit for a guy like u, so just tell you some. 

And most from the dramas I choose, the female lead is dominant even they are poor. Because you dont like the typical girl who got in trouble.

A Secret Affair

Witch's Romance

New drama, Witchs Court sorta describes your criteria 

 Alpha101:

Hey! So I'm a guy, and I like Kdramas. The problem is that so many  kdramas are tailored towards women. You know like the female main character is poor or in trouble, and then the handsome rich nice guy or bad boy comes in and they start a romance.

What I'm looking for is a Kdrama with a Male lead who is poor and humble. And then a rich, beautiful, and successful woman comes into his life and falls in love with him. And I would really like the lead to be likable, so no asshole jerks please. 

Ones I liked that kind of fit this category:

-Angel Eyes

-Innocent man

-That fool

-Ugly Alert

-That winter, the wind blows

Thanks!

You should totally try tatta hitotsu no koi. It has all the criterias u r looking for. The male lead is very very poor and the girl is very rich and they fall in love. But Its a japan drama.. 

drama for guys but not romances, wise prison life / prison playbook.. amazing drama

Ruler of Your Own World.

He's an ex-pick pocket trying to keep clean after a stint in prison. She's a struggling musician from a rich family.

I suggest:

  1. City Hunter
  2. Healer
  3. Remember War of the Son
  4. A Beautiful Mind

Historical:

  1. Warrior Baek Dong Soo
  2. Rebel Thief Who Stole the People
  3. Inspiring Generation

And just because I think they will appeal to you:

  1. The Bridal Mask
  2. Cruel City
  3. God's Gift - 14 Days

P.S. Ji Chang Wook tends to select roles with the dynamic you are looking for, so you might check out his profile. Shame he just went off to the Army. 

Totally off subject, if you're up for a good movie, I think you'd like Confidential Assignment

Some of these are better than others. I'm recommending them based on their relevance to what you're looking for, and I've underlined the ones I personally liked best. 

  • Live Up to Your Name (medical / time travel) - the FL is a confident, beautiful, and successful surgeon in modern times. The ML is the greatest doctor of oriental medicine of all time, but because he's not of noble birth, he cannot advance to become an imperial physician or spend any wealth he makes, so he's de facto poor. His personality is generally humble (although he can come across as arrogant in certain situations, especially when he's facing off against a rival doctor he doesn't like) and quite goofy much of the time, but he can be serious about the things he cares about / when the situation calls for it. One of the best dramas of the year IMO. 
  • I Hear Your Voice (Noona / law with a sci-fi / fantasy element) - a young boy who can read peoples' thoughts witnesses his father's murder but is too young to be believed in court. An older girl saves him  / ensures his father's murderer goes to prison when she testifies. Years later, the ML is in high school, the girl has grown up to be a lawyer, they meet again, and the murderer finishes his sentence. While the ML is in high school and living alone, he is not poor (he lives off an insurance payout if I remember correctly). While the FL is successful in the sense that she's a lawyer, she's not perfect. 
  • Dream High (high school / music / dance) - there are two MLs. One is definitely poor and humble, the other sort of fits that description. The FL is pretty, conceited, and a successful vocalist. The boys fall for her first, and (major spoiler) the FL ends up with the poor humble ML who seems like a SL until the end
  • Pinocchio (revenge / cohabitation / reporters) - the ML is adopted by the FL's grandfather, who mistakes him for his long-lost son / the FL's uncle. The ML has to pretend to be stupid in order to keep up the pretence because the grandfather goes into shock whenever his delusion begins to unravel. So the ML starts out as a humble country bumpkin who has to pretend to be stupid. The female lead is pretty and driven. Both of them also have complicated plot points related to their parents (particularly the ML, whose father was framed as responsible for a fire) and go on to pursue careers as reporters after school.  
  • Queen In Hyun's Man (time travel) - the ML is from ancient times, and is very clever and humble. The FL is a somewhat self-centered, beautiful, and successful actress. She falls for him first. 
  • My Only Love Song (time travel / Netflix original) - similar to Queen In Hyun's Man, except the actress goes back in time instead of the ML going from the past to the present, and it's a Netflix drama (so not quite the same production value) / more of a comedy. 
  • Gu Family Book (historical / fantasy) - the FL is the pretty daughter of ... I forget the correct term, but he's a master swordsman / head of a dojo-esque training school. The ML is kind, humble (although he sometimes puts on a show of being arrogant), adopted by a wealthy family but never fully accepted as an equal to his siblings, and a half-human half-immortal. The FL falls for the ML first. 
  • Strongest Deliveryman - both the ML and FL are talented food deliverers. Neither of them are wealthy. The FL is well established as the best in her location. The ML travels from location to location, and is generally the best wherever he goes. The ML is kind and humble. The female lead is strong and pretty. 
  • The King in Love (historical) - The ML is the best friend, relative, and de facto body guard of the crown prince. He goes where the prince goes and follows his orders, so although he's not poor he's the humble and responsible one of the two. The FL is gorgeous, smart, a good athlete, and the daughter of a wealthy family.
  • Hwarang (historical) - the ML is raised in poverty. He's strong, principled, and humble. He pretends to be the FL's brother after her brother is killed. The FL is the daughter of a noble and a servant. She's pretty, smart, and talented. 
  • You Who Came from the Stars (fantasy / sci-fi) - the ML is not poor or humble (he's actually a very wealthy and aloof professor), but he's an immortal extraterrestrial who is isolated from the world and in some respects he's quite innocent. He doesn't act like a rich playboy. When the FL comes into his life (she's a wealthy and successful actress who moves in next door to him) he slowly falls for her / comes to appreciate human interaction.