Which are saddest characters/series you can think of?
Just mention the character and the name of the series, if you do. And you can mention books and novels, too.

There are times when you will miss what you never had. I wonder how you will find what you so desperately need.

ohhh a sad manga would definitely be Watashitachi no Shiawase na Jikan It's a touch of tragedy and realism(: i cried a bucket full of tears for this.
for sad anime id recommend:
sola
clannad
anohana
elfen lied
[“You said that the hours of every day are trash. However, that is the way someone lucky enough to welcome the next day thinks."]-Watashitachi no Shiawase na Jikan

Mahoroba no Hibi was the first manga that made me shed a tear. Though it say so on here, I wouldn't classify it as shounen-ai.
Akazukin to Yasashii Ookami is great and sad. It has no writing, so it gets interesting when you start figuring out what's happening.
I seem to recall that A Boy Who Fishes Dreams is sad enough to be on the list, but I don't really remember what it was about.
Le theatre de A is a collection of one-shots. The sad story is the sixth ("Till dawn").
The second story (chapter 2) of Tsuki no Waltz is sad, but at the same time makes you smile.

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