So I was thinking, it seems like in most dramas the girl always suffers more, in romance dramas especially (you know, because she's the poor one, or she's bullied by the guy's parents, ex girlfriends etc etc) so what are some dramas that come to your mind where it's the guy who suffers more? (Wow that certainly sounds creepy I'm sorry xD) The first one I can think of is Cruel City maybe? (which isn't a romance drama obviously, so any recommendation/genre is fine ^^) 

Ugly Alert
Jejoongwon
Dream High
Family's Honor
Plus 9 Boys
Discovery of Romance
May Queen
Swallow the Sun
Valid Love

http://mydramalist.com/10874-valid-love

The drama isn't perfect but also not half as bad as many of the comments may make you think! The main character is a man who suffers a great deal. 
Good Doctor
Hi My Sweetheart
Pinocchio
Flowers for Algernon
Faith
Dr. Frost
Satorare
Zeni Geba
Dr. Koto Shinryojo

I didn't finish Pinocchio and Faith, so I can't say for sure how their situation will go, but I think the others might be what you're looking for :)
All About My Romance
Witch's Romance

I don't know if these are exactly what you're looking for. The guy likes the girl and chases her, but something gets in the way.
Woody Sambo- He loses everything and has to rely on her and her family for help.