Sad 2,625 members · 4,385 stories
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I'm looking for stories that would break my heart.

Can anyone recommend anything?

Tis may work the desired way.

6162368
You're adopted.

Hopefully some of these tickle your sadness fancy. Enjoy! :D

TThey're Gone
Tirek and I did not negotiate; my friends are gone, and he is dead. The worst part? I won.
JackRipper · 1.4k words  ·  410  26 · 7.9k views
EThe Tarnished Crown
Heavy is the head that bears the crown. Light is the heart that shares its burdens.
Amber Spark · 11k words  ·  409  16 · 5.8k views
EA Wooden Heart
Alone, a young timberwolf must try to survive in the wilderness. Survival above all else.
Trials · 8.4k words  ·  1,022  12 · 10k views
TDearest Fluttershy
Discord deals with death for the first time.
Terrasora · 4.7k words  ·  1,291  13 · 19k views
TTyrant
Canterlot has fallen at last, and six heroes go to face the tyrant of Equestria: Princess Twilight Sparkle. What they find, however, is not at all what they expected. — A reaction to Tyrant Sparkle fics.
PaulAsaran · 3.7k words  ·  2,580  69 · 26k views

[Unpublished stories cannot be embedded]

TForever in Your Heart
It has been a thousand years since the great Dragon War. Princess Twilight visits her old friend Spike one day only to find out that he wants her to end his life. But despite his constant pain and misery, can she bring herself to do it?
Private Page Turner · 4.9k words  ·  14  2 · 828 views
TThe Better Angel
The death of one Princess, the destruction of another.
ArguingPizza · 9.7k words  ·  313  16 · 6.9k views

I'm certain I can't recommend anything up to date with the current canon, but here a few dating back to first and second seasons. I know it makes it harder to immerse oneself because of that, but they are still really good at being sad.

This one is an oddball since it's done abstractly, but it's still good for a tear or two at the right moments, and it leaves you with the bittersweets at the end. - Somewhere Only We Know
Oh yeah, then there is this really really odd story. I guess the fact you say it's sad is a bit of a spoiler? I dunno, I know that author left the sad tag off for a reason, but hey whatever. - Bon Bon Bon Bon Bon Bon
And here is a few of the Season 1 & 2 canon stories, as long as you can enjoy stories with pre-Alicorn twilight, then I'm sure you'll get what you want out of at least one of them.
The Magic Never Fades Away
Lone Black Train
The ever infamous (and famous enough you've probably read it) In Memory Of. At the time of it's first appearance in the feature box, this one was the go-to "break your heart" sadfic for unicorn Twilight. Hell, I've read it a dozen times and it still elicits that feeling from memory alone.
This one is a favorite of mine that is also popular enough I'm sure you've read, but just in case. - The Keepers of Discord
Forever young is a cute but also sad story about Discord and Fluttershy
Where all Roads lead
Of the Valley - This one was written by a friend of mine. Promotional favoritism aside, he did a really good job with this one, and made it into the Twilight's Library almost literally before they closed the group.
My Best Friend -An EqG story that's worth mentioning.
and lastly a really well done story involving only OC's. "Why?"

6162368 Here are two of mine that should do it for you:

TPrincess of Friendship
After Twilight’s stream of successes, she’s confident that nothing can go wrong. Is she due for a lesson?
Bad Dragon · 5.4k words  ·  290  46 · 7.9k views

[Adult story embed hidden]

IT WORKED:fluttercry:

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