Romance with awkward, gentle, emotionally wounded male lead?

Recently watched Soratobu Kouhoushitsu and Arifureta Kiseki and realize that I really dig this kind of male lead in romance. A somewhat beta type, who's mostly awkward and clumsy, but possess a gentle heart and polite attitude, and carry some emotional wound. I prefer the female lead to be somewhat fragile in appearance, but if it's too much to ask then I'll take anything as long as the female lead isn't that much superior than the male lead. In short both of them are more to the loser type and both are helping each other. Also, the romance doesn't actually have to be the main focus. I guess that's all. Thanks for the recs! 

Note: I'm open to any kind of rec, be it movie, drama, non-asian movie/drama, webtoon, manga, anime, etc as long as they're available with english subs!

Thanks for the rec! Hi my sweetheart sounds the closest to what I'm looking for, as for Queen In Hyun's Man I'm planning to retry it someday, I didn't drop it because it was bad, it was just not what I was looking for at the time

1: Zenkai girl

This drama has a strong ambitious female lead and a underachieving gentle male lead who is emotionally way warmer than her.  He's going to teach her about being kind and compassionate and patient...especially toward the kid she's assigned to babysit. Their relationship is really touching. 

- http://mydramalist.com/2627-zenkai-girl -

2: Otomen

A high school boy hides his softer side (reading shojo manga, loving to cook and sew, dreaming of romance) behind the mask of being the coolest guy in the school, an expert in kendo fighting. She on the other hand, is a female kendo fighter who transfers to the school and who is a complete tomboy. Of course, both fall in love.

  - http://mydramalist.com/120-otomen -

3: Soredemo, Ikite Yuku

This drama tells the story of two people traumatized by the same crime. One is the older brother of the victim ( a 5 year old girl), and the other is the younger sister of the murderer. Both are wounded and awkward, but somehow a relationship starts between them. This drama is a must-watch, and got Six Japan Academy Awards. I highly recommend it.

- http://mydramalist.com/2662-soredemo-ikite-yuku -

soredemo ikite yuku XD
but you already see and love it

itsuka koi ....
itsukoi is basically a very mild, romance, not too dark version of soredemo :D

and Gin Nikan too
:)

I would recommend the Taiwanese drama An Innocent Mistake (2012), one of my Taiwanese drama favorites. 
The male lead, Zheng Yu En, fits your above mentioned description perfectly, in my opinion.
He is awkward and clumsy, but has a gentle heart and polite attitude, and carries an emotional wound. 
The female lead is not exactly fragile, but she has her own issues to overcome as well. 
It's an underrated tw-drama but it was a favorite among critics. 

:)

rich man poor woman. oguri shun is super intelligent but super awkward in romance here. he also has wounded past

Although I haven't watched it yet, DATE sounds like it fits your bill. And apparently it's super funny too. I'll be watching it very soon myself.