I'm a bit of a masochistic reader, but I like to me emotionally beaten by my mangas, and I'm looking for whatever I can find that is similar to the following:

Kimi ga Nozomu Eien,
School Days,
Bitter Virgin,
Ressentiment,
Chisa x Pon.

Something where there is tragedy at beginning or middle of relationship, usually involving some kind of "physical romance"/sexual trauma, and the troubling work-through that accompanies it. I don't mind if it's also geared for comedy, seinen, josei, whatever, and smut/H content is fine as long as it is relative to the plot.. (and the plot being soul-crushing agony, muhahAHA!)

I appreciate any suggestions and advice on what to read next, it's fine whether in english or moonspeak, as I can read both.

Thanks in advance.
--Fe/sar

Life
Knife
The Flower Of Evil
Higurashi no Naku Koro ni - Onikakushihen && the other stories accompanying it.

I like Bitter Virgin too. Great read. But I'm not into hardcore tragedies. The only other one I have on my list is Boku no Hatsukoi wo Kimi ni Sasagu but it's really good. I also read Mucha Kucha Daisuki but it was so sad I hated the ending.

Try Dear Friends I haven't read it yet, and it's not a Romance but you might like it.

I also like this kind of manga, and these are works I have found to be of the kind:
Mars - This is quite well known so you may have read it already. Unquestionably one of the best manga dealing with emotional trauma.
Cat Street - About a girl suffering from trauma at having failed at acting. She constantly lives with that burden on her back and accomplishes little in life, greatly written.
Tenshi no Uta - Two people from different worlds who have feelings for each other can only see each other at a distance, very well written.
Let Dai - This is an amazing Korean manhwa with some shounen-ai tendencies, but highly recommended if you don't mind that. One character deals with trauma from severe bullying, another from rape, and another two from their love/hate relationship.
Deep Love - Ayu no Monogatari - A short but excellent manga dealing with death.

I hope you give some of these a try and enjoy them!

I would definitley recommend

Tomoyo After

Cry out for Love at the Heart of the World

Ah, thank you all for your suggestions so far, I've been able to find most of them, and did find a few to be very enjoyable.

--
Fe/sar

Quote from Mega2155

Try Dear Friends I haven't read it yet, and it's not a Romance but you might like it.

Ah, I recommend that too, but you might want to get your kleenex ready 😃

SaiKano
Kareshi Kanojo no Jijou(kinda angsty in the middle, dunno if u call it tragedy)
Nana(if you like it look for the mangaka's other works)
Please Save My Earth
Ai-Ren(sad but sweet in the end)
Tsuiteru Kanojo
Hoshi no Koe

Some of it might not really be all that tragic but I hope it helps

It's kinda old but candy candy is considered a drama/tragedy/romance as well as slice of life 🙂

I haven't failed. I have found 10,000 ways that don't work.

-Thomas alba Edison

Eden no Hana similar theme to bitter virgin.
Fullmoon wo Sagashite dying girl wants to become a singer. Accompanied by a couple of shinigamis, which is a job for people who have suicided. Closest I've come to crying (because of a series) was this manga. I will say the end isn't great tho >_>
Kagerou Nostalgia it isn't really focused on relationships, (genre is "Adventure, Fantasy, Shounen" here) but the main character is rather messed up due to uh 'sexual trauma'. Emotional for me cos I love the characters.