Ask a Pony/Tear Jerker

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• Some of the Ask Pony blogs over on Tumblr can be this from time to time.
• From Ask Twilight Sparkle, "Twilight Reads Cupcakes". If you didn't hate the fic, you will after this. The second part is more depressed, but its ending is quite something.
  • Here, read Twilight's response to her updates. It just breaks your heart so slowly.
  • When Twilight is asked what will happen to her and Spike when he grows up. (Colored version here Let's just say manly tears were shed... A video was made of it, set to Paul McCartney's "Here Today".
    • Now there's a flash video based off of it. Warning: Manly Tears will be shed!
• This Ask Pinkamena Diane Pie, in its own, sick way. She's a psycho murderer similar to her Cupcakes incarnation, but this comic indicates that she knows what she's become, knows she can never go back, and knows she desperately wants to.
  • Fluttershy's death.
  • Pinkamena and Scootaloo's relationship. Despite everything, Pinkamena really loves and cares about the filly.
• Look at what Evil!Octavia did to Vinyl Scratch's Cool Shades. Look at those eyes. How do you not feel sorry for poor Vinyl?
• This ask blog of Crapplejack
• Whirly.
• But... I'm not like that at all...
• Believe it or not, the Prince Blueblood tumblr produces one: You are now aware that every time you asked me "Why aren't you an alicorn" you broke my heart
• Someone took a Wonderbolt that briefly appears in "The Best Night Ever" and built some fanon with her - Echo the blind Wonderbolt. This post puts her in Woobie territory.
• Even Lil' Miss Rarity has its moments.
  • Why she likes being called "Mommy".
  • Shortly after the hospital visit, Rarity shows remorse for her actions, especially killing her cat.

Rarity: Mommy misses you, Opal…

• • Becomes Harsher in Hindsight when Rarity finds herself in the pre-Grimdark world, where everything's back to normal, and realizes she doesn't want it. But in order to get that world back, she realizes she'll have to murder Opal again. She really doesn't hesitate.
• Even Paranoid Twilight, of all tumblrs can produce some...
  • This. Also a Crowning Moment of Heartwarming.
    • These parts. Poor Twilight...
• Hey, Surprise, how are...oh...please don't cry...
• From Jappleack. Jappleack!
  • And now this. You know it's heartbreaking when she turns down her Trademark Favorite Food by the grief.
    • In fact, ever since Applebloom's death in Shed.mov, the entire blog took a left turn into depressing.
• Ask Discord Whooves gives us this Poor Derpy.
  • Not to mention some new information.
  • Heck, several posts across the blog imply that the Doctor (similar to Pinkamena above) knows what he's become, hates himself for it, but doesn't know how he can ever go back. And despite his protests, he does seem to suffer from incredible loneliness without Derpy by his side.
  • This post which is what happens when he's given crayons, starts out funny...then deteriorates to this. Of course, one could argue that it's all played for (dark)laughs.
• The ongoing drama between the new Pinkamena and her..."boyfriend", The Master. Being as obsessed with him as she is, hearing that he might have been cheating on her had quite an effect. So far, it seems that it'll take quite some time for either of them to totally recover.
• From the Twixie Blog, Nyx and Midnight managed to get through Pinkie Pie's hole in the Fourth Wall and were essentially adopted by Twilight and Trixie. Trixie realizes eventually they'll have to let them go back to their families.
  • The "Hazel" arc that finished on May 31, which actually makes Hazel sympathetic. Hazel!
• Not even Hot-Blooded Pinkie is exempt.
• This peek into Statued Discord's past.