Pool: Heart-Breaking

Scenes that make your heart yearn to reach out, to make things better. Situations you can only wish had turned out better for those involved.

The tears-&-sniffles-inducing opposite of Heart-Warming, but not so disturbed and 'wrong' to be Soul-Crushingly Depressing.
amputee blush english green_eyes iceo208 katawa_shoujo necktie red_hair redhead short_hair solo tezuka_rin rating:Safe score:2 user:Gelbooru brown_hair clannad family furukawa_nagisa ghost hug husband_and_wife okazaki_tomoya okazaki_ushio rating:Safe score:2 user:Gelbooru barefoot blood death feet highres inubashiri_momiji kobushi short_hair tail touhou traditional_media white_hair wolf wolf_ears wolf_tail rating:Safe score:2 user:Gelbooru 2girls ayakashi_(monkeypanch) bad_id blue_hair blush bow fujiwara_no_mokou hat kamishirasawa_keine long_hair multiple_girls silver_hair suspenders tears touhou rating:Safe score:0 user:Gelbooru comic dan_kim highres shiraki_aeka silent_comic yume_miru_kusuri rating:Safe score:1 user:Gelbooru chaba_(hortensia) donation_box hakurei_reimu japanese_clothes lowres miko poverty touhou rating:Safe score:0 user:Gelbooru anya_alstreim arthur_(code_geass) c.c. cecile_croomy code_geass cornelia_li_britannia euphemia_li_britannia gilbert_g.p._guilford gino_weinberg jeremiah_gottwald kallen_stadtfeld kururugi_suzaku lelouch_lamperouge lloyd_asplund milly_ashford nina_einstein nunnally_lamperouge rivalz_cardemonde rollo_lamperouge schneizel_el_britannia shinozaki_sayoko shirley_fenette rating:Safe score:1 user:MoeImouto asuna_(sao) blush brown_hair closed_eyes crying eyes_closed freckles frown gloves hair_ornament hairclip hammer highres jewelry lisbeth multiple_girls open_mouth pink_eyes pink_hair ring sword_art_online translated trembling wedding_band wedding_ring rating:Safe score:0 user:danbooru blonde_hair blue_hair bow braid broom brown_hair detached_sleeves grin hair_bow hakurei_reimu hat highres kirisame_marisa lonely red_eyes remilia_scarlet sad short_hair smile tokoroten_(hmmuk) touhou wings witch_hat yellow_eyes rating:Safe score:6 user:Gelbooru 3girls blonde_hair blue_hair detached_sleeves fading green_hair grin hat hat_on_chest hat_removed headwear_removed hinami_(hinatamizu) hug japanese_clothes kochiya_sanae letterboxed miko moriya_suwako multiple_girls petals smile tears touhou yasaka_kanako yellow_eyes rating:Safe score:0 user:Gelbooru 1girl blue_dress blue_hair broken cloudy_sky dress harusame_(unmei_no_ikasumi) heterochromia highres karakasa_obake long_tongue shirt solo tatara_kogasa tongue touhou umbrella wet wet_dress wet_hair rating:Safe score:1 user:danbooru 1girl blue_eyes blue_hair blue_skirt crying ears gutter heterochromia holding_umbrella karakasa_obake long_sleeves looking_down rain red_eyes short_hair sitting skirt socks streaming_tears tatara_kogasa tears touhou umbrella wariza water wet wet_clothes wristband rating:Safe score:0 user:danbooru 1girl blonde_hair blue_eyes blush boots camouflage daito gloves gun hat l85 military original short_hair smile solo weapon rating:Safe score:1 user:danbooru 1girl alice_margatroid birthday cake food hirasato lonely pastry sad solo tears touhou translated rating:Safe score:2 user:Gelbooru 2girls apron_grab bad_id hands hat hat_removed headwear_removed kawanabe kirisame_marisa kneeling multiple_girls no_eyes patchouli_knowledge touhou witch_hat rating:Safe score:0 user:Gelbooru artist_request carrying cross cubone flower grave kneeling lowres pokemon pokemon_(game) red_(pokemon) red_(pokemon)_(classic) source_request rating:Safe score:1 user:Gelbooru bad_id blue_hair cirno flower hat letty_whiterock multiple_girls nejime short_hair tears touhou wings rating:Safe score:0 user:Gelbooru 1girl ayakashi_(monkeypanch) bad_id bat_wings blood blue_hair blush hat letterboxed outstretched_arm outstretched_hand profile reaching red_eyes remilia_scarlet rough short_hair sunlight tears touhou wings wrist_cuffs rating:Safe score:1 user:Gelbooru closed_eyes death injury mochizuki_anko multiple_tails ninetales no_humans pokemon pokemon_(creature) sad shiny shiny_pokemon snow tail tears vulpix wound wounded rating:Safe score:5 user:danbooru 2girls comic english kill_la_kill kiryuuin_satsuki matoi_ryuuko monochrome multiple_girls radiostarkiller scar spoilers tears rating:Safe score:0 user:danbooru 2girls baby crying eyebrows kill_la_kill kiryuuin_ragyou kiryuuin_satsuki masu_(masmaasn) matoi_ryuuko multiple_girls out_of_frame spoilers tears thick_eyebrows young rating:Safe score:0 user:danbooru 71 blood child comic holding kill_la_kill kiryuuin_ragyou kiryuuin_satsuki monochrome mother_and_daughter spoilers sword tears translation_request weapon younger rating:Safe score:0 user:danbooru 1boy 1girl black_hair blonde_hair blood gamagoori_ira hand_on_another's_head injury junketsu kill_la_kill kiryuuin_satsuki mow_(mowmowmuu) open_mouth shouting tears rating:Safe score:0 user:danbooru