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51569194
Size: 600x513 | Tagged: safe, artist:warpout, princess celestia, alicorn, pony, lullaby for a princess, g4, agony, animated, crying, depressedia, despair, feels, female, heartbreak, mare, open mouth, regret, sad, sadlestia, solo, tearjerker, tears of pain
57843
Size: 1209x1080 | Tagged: safe, artist:warpout, princess celestia, alicorn, pony, lullaby for a princess, g4, black background, cropped, crying, depressedia, despair, emotional, heartbreak, nose in the air, regret, sad, sadlestia, simple background, tearjerker, tears of pain
29141819
Size: 1600x1700 | Tagged: semi-grimdark, artist:trazodoned, apple bloom, applejack, earth pony, pony, g4, my little pony: friendship is magic, somepony to watch over me, alternate ending, bad end, corpse, crying, death, despair, feels, female, fire swamp, mare, realization, sad, thousand yard stare
881239
Size: 3000x4000 | Tagged: safe, artist:emerald-light, cozy glow, pegasus, pony, g4, crying, despair, eyes closed, failure, falling, female, filly, foal, guilty, harsher in hindsight, light, regret, remorse, sad, sadness, shine, sobbing, solo, tears of pain, tears of sadness, teary eyes, void
150191250
Size: 800x450 | Tagged: safe, screencap, spike, twilight sparkle, alicorn, dragon, pony, father knows beast, g4, my little pony: friendship is magic, season 8, abuse, accusation, adventure in the comments, animated, baby dragon, claws, crying, debate in the comments, discussion in the comments, disowned, duo, duo male and female, eye shimmer, fangs, feels, female, floppy ears, folded wings, frown, gif, heart, heartbreak, lip bite, male, mare, nickelodeon, not cool, oh no he didn't, ouch, pointing, raised eyebrow, sad, savage, shocked, subtitles, talking, tearjerker, teary eyes, text, this ended in tears, tragedy, twilight sparkle (alicorn), twilybuse, winged spike, wings, x-ray, x-ray picture
38751368
Size: 1200x900 | Tagged: semi-grimdark, artist:heir-of-rick, spike, twilight sparkle, alicorn, dragon, pony, g4, and i am iron man, avengers: endgame, broken horn, crying, element of generosity, element of laughter, element of loyalty, element of magic, elements of harmony, feels, female, harmonic gauntlet, harmony gauntlet, heartbreak, heroic sacrifice, horn, imminent death, infinity gauntlet, male, mare, marvel, sad, self sacrifice, series finale, spoilers for another series, tearjerker, teary eyes, twilight sparkle (alicorn)
797108267
Size: 3200x1800 | Tagged: safe, artist:fidzfox, princess celestia, twilight sparkle, alicorn, bird, pony, unicorn, anthro, unguligrade anthro, g4, book, clothes, comforting, crying, cute, dead, death, drawing, dress, eraser, eyes closed, feels, female, filly, filly twilight sparkle, hug, kneeling, lamp, mare, maternal instinct, momlestia, open mouth, paper, pencil, sad, sadness, sadorable, skirt, sundress, sunlight, tearjerker, tears of pain, teary eyes, this ended in tears, tissue box, unicorn twilight, yellow dress, younger
681033
Size: 1920x1080 | Tagged: safe, artist:warpout, princess celestia, princess luna, alicorn, pony, lullaby for a princess, g4, bedroom, crying, feels, female, mare, pink-mane celestia, royal sisters, s1 luna, sad, sisters
14919720
WebM
Size: 1920x1080 | Tagged: safe, artist:warpout, nightmare moon, princess celestia, princess luna, alicorn, pony, lullaby for a princess, g4, absurd file size, animated, banished to the moon, banishment, canterlot, canterlot castle, crying, eclipse, elements of harmony, fan animation, female, fight, filly, filly luna, foal, forest, it came from youtube, legendary, lullaby, luna's banishment, magic, mare, mare in the moon, memories, moon, music, night, pink mane, pink-mane celestia, planet, ponyphonic, raising the sun, s1 luna, singing, sleeping, solar eclipse, song, sound, space, sun and moon, tears of pain, time-lapse, video, webm, woona, younger, youtube link
881345
Size: 800x800 | Tagged: safe, screencap, pinkie pie, equestria girls, five stars, g4, my little pony equestria girls: better together, animated, apron, clothes, cropped, crying, despair, devastation, female, gif, heartbreak, miserable, sad, server pinkie pie, shop, sobbing, sorrow, tearjerker, waitress, we're doomed
103150124
Size: 600x337 | Tagged: safe, applejack, derpy hooves, discord, fluttershy, pinkie pie, princess celestia, princess luna, rainbow dash, rarity, twilight sparkle, alicorn, draconequus, earth pony, pegasus, pony, unicorn, equestria daily, g4, female, fluttercry, grave, gravestone, heartbreak, hub drama, hub logo, hubble, it's happening, male, mane six, mare, pinkie cry, rest in peace, sad, sad pony, sadbow dash, sadjack, sadlestia, the end, the hub, unicorn twilight
528414
Size: 623x642 | Tagged: safe, applejack, fluttershy, pinkie pie, rainbow dash, rarity, twilight sparkle, alicorn, pony, g4, despair, female, hug, image macro, mane six, mare, realization, twilight sparkle (alicorn)
5918169
Size: 2000x1000 | Tagged: safe, artist:rizcifra, princess celestia, princess luna, alicorn, pony, friendship is magic, g4, my little pony: friendship is magic, adobe imageready, cosmic love, cute, cutelestia, duality, duo, duo female, eyes closed, feels, female, first celestia image on derpibooru, florence and the machine, frown, hug, looking up, lunabetes, mare, royal sisters, s1 luna, sad, sadlestia, sadorable, sibling love, siblings, sisterly love, sisters, sitting, song reference, spread wings, window, winghug
7791085190
Size: 640x360 | Tagged: safe, artist:superedit, edit, edited screencap, screencap, rainbow dash, scootaloo, pegasus, pony, g4, my little pony: friendship is magic, season 5, tanks for the memories, adventure in the comments, animated, bad end, bathrobe, big sister, bittersweet, clothes, crying, cute, dashabetes, dashie slippers, feels, female, filly, floppy ears, foal, implied death, mare, nightgown, nuzzling, prone, robe, sad, scootalove, siblings, sick, sisterly love, sisters, slippers, smiling, talking, tearjerker, the great and powerful superedit, this ended in tears, this will end in tears and/or death, woobie
8610417
Size: 1120x5625 | Tagged: safe, artist:haretrinity, princess cadance, princess celestia, princess luna, shining armor, twilight sparkle, alicorn, pony, g4, comic, despair, female, heartbreak, immortality blues, lesbian, mare, nightmare cadance, nightmare fuel, nightmarified, ship:twilestia, shipping, twilight sparkle (alicorn)