I'm looking for romance between 'sad' characters.

Something like
Diamond Dust (Kang Hyung-Gyu)
The Other Side of the Mirror
...to a lesser extent maybe even Oyasumi Punpun.

Things I'm looking for:
Poverty
Mental/psychological problems
Illness
Cynicism/pessimism
Family situations/Dysfunctional families
Hopelessness
Depression
Trauma/tragedy

..and all that bad stuff. They don't need to meet all. One is good.
Both partners of the relationship must have/had some kind of problem.
But it doesn't mean it has to end in tragedy.

Edit: I put linked the wrong Diamond Dust. Happens every single time. It's fixed now and hopefully everyone got what I meant. 😔 Also, thank you for all the suggestions so far.

Favorite Art:
Oboreru Knife
19 Days
Gangsta

Watashitachi no Shiawase na Jikan
Annarasumanara

Just realized that you've already read Watashitachi no Shiawase na Jikan. I don't know, most of the story has one "sad" character, but rarely both. If you're ok with the pair being side character, Utsuro no Hako to Zero no Maria (Novel) kinda fit.

Maybe Grisaia no Kajitsu not sure though (I think they all have some kind of mental trauma). According to MU no chapters out but Quantum scans did first chapter of it. Its based on an VN which is fully fantranslated...

Most of these suggestions I feel fit what you're looking for, others ... to an extent and may be stretching it a bit.
Hana no Namae Best fitting suggestion
Hana wa Knife o Mi ni Matou
H2O
Meteor Methuselah
Aoi Kiseki
Basilisk
Koyoi Oto Furu Sora no Shita
A House in Venice
Diamond Life
Melody Drifting in the Rain
Nemurihime - Yume Miru You ni Koi Shiteru
Koi Tomurai
Tobenai Tori
S no Kaikoroku
Visukiisu no Akai Ningyou
System of Romance
Carpe Diem
Escape from High-School GirlsThis one really is a stretch, but it's a oneshot.

Kurokami no Helga / Bride (Aivan)(Saw these were in your complete list after posting this,but I just couldn't take them out from this edit so I made this note, heh)

Some don't have both partners that have/had the tragic things happening, but I feel has that same vibe you are looking for. I hope these help.

Yes yes, I know I make longwinded comments, but that's just me >.<
I should proof read my comments more, but I won't...
So keep in mind I'm filled with typos

Check out FAQ and Forum Rules if you haven't yet.
For errors linking in threads

Ai-Ren?

The Deep Love series, can't believe no one mentioned it yet:
Deep Love - Pao no Monogatari
Deep Love - Ayu no Monogatari
Deep Love - Reina no Unmei
Deep Love - Host

Enjoy... 🙂

[img]http://img267.imageshack.us/img267/4466/princesswallpaper2560x1.jpg[/img]

"In a world where most people would be crazy, then it would be normal to be crazy and crazy to be normal... but then again, if you were normal, then you would be crazy... isn't it crazy what a paradox a little craziness can create?"

Saikano

Sarcasm just doesn't work over the internet.

Boku no Hatsukoi o Kimi ni Sasagu
Tada, Kimi o Aishiteru
100% Perfect Girl - not the starting, in the middle part(slowly progressing towards it).
Emma
Fruits Basket - in a way, yes.
Hoshi no Koe - forced to leave one another.
Koi Kyokusei
Kono Koi wo Wasurenai. - third story.
Love in the Mask
Tokyo Crazy Paradise
Natsu no Kakera - first story.
Wasure Yuki (AMANO Shinobu)
Six half
Kagen no Tsuki
Basara
Kimi ga Uso o Tsuita

"A Lady Needs Time To Prepare. Even If It Takes A Year, A Gentlemen Must Wait." ~ Wilhelm Mölders(Emma)

Ooku Not the first book, but everything after is sad.

I second SaiKano. It's very very depressing. I'd like to recommend 3gatsu no Lion too.

It's about a young genius shogi player who's trying to overcome his tragic past, along with the physical and mental pressure from his work. He's also coping with others' expectations of him being a young genius and with the rather hostile atmosphere of his foster family.

And also Video Girl Ai

[img]http://vdexproject.net/p/46642/partymini.png[/img]