Danbooru

Read the rules before proceeding!

Collection: Heart-Breaking

Scenes that make your heart clench.

Do not automatically add any sad pictures (i.e. character who is just crying, being lonely, "poor little thing", etc.) unless you can see why that hurts.

See also:

Blacklisted:
2girls admiral_(kantai_collection) bride comic commentary_request cosplay crossover detached_sleeves fate/grand_order fate_(series) fujimaru_ritsuka_(male) fujimaru_ritsuka_(male)_(cosplay) greyscale hair_ornament hairband hairclip haruna_(kantai_collection) headgear highres japanese_clothes jewelry kantai_collection mash_kyrielight military military_uniform monochrome multiple_girls naval_uniform nontraditional_miko ribbon-trimmed_sleeves ribbon_trim ring t-head_admiral tears translated uniform yukanii_(yukani_0721)
2girls azur_lane check_translation comic commentary_request crossover crying door gloves greyscale hakama_skirt highres japanese_clothes kaga_(kantai_collection) kantai_collection long_hair monochrome multiple_girls partly_fingerless_gloves rokushin_gattai_godmars side_ponytail tears translated translation_request waving yukanii_(yukani_0721) zuikaku_(kantai_collection)
1girl :d ^_^ ^o^ aardwolf_(kemono_friends) animal_ears bare_shoulders black_gloves black_hair black_neckwear blush close-up closed_eyes collared_shirt face facing_viewer fading gloves hair_between_eyes hand_up highres kemono_friends light_particles multicolored_hair necktie open_mouth sad_smile shirt short_hair simple_background sleeveless sleeveless_shirt smile solo streaked_hair stream tears white_background white_hair wing_collar yasume_yukito
1boy blizzard coat comic emiya_kiritsugu fate_(series) from_behind greyscale kneeling monochrome outdoors pants sen_(0snow) short_hair snow translated
2girls akino_kabocha blush closed_eyes comic dragon_horns fan fate/grand_order fate_(series) folding_fan from_side fujimaru_ritsuka_(female) greyscale horns japanese_clothes kiyohime_(fate/grand_order) long_hair looking_at_another monochrome multiple_girls open_mouth profile scrunchie short_hair smile translated white_background
4koma anchovy blonde_hair bow comic crying drawing drill_hair fang girls_und_panzer green_hair hair_bow highres jinguu_(4839ms) katyusha kindergarten_uniform mother_and_daughter multiple_4koma orange_eyes shadow sleeping translated twin_drills younger
2girls blood comic death greyscale kill_me_baby kiss monochrome multiple_girls oribe_yasuna petsematary school_uniform short_hair sonya_(kill_me_baby) tears translated yuri
1girl ahoge bandaid bandaid_on_face brown_hair commentary crab crying crying_with_eyes_open highres holding kantai_collection nhk_(artist) oboro_(kantai_collection) plate school_uniform serafuku short_hair solo tears translated
1girl alternate_hair_color aoba_(kantai_collection) black_legwear blue_eyes blue_shorts blush book breasts check_translation crying crying_with_eyes_open eyebrows_visible_through_hair grey_hair hair_between_eyes highres holding holding_book holding_pencil kantai_collection medium_breasts neckerchief nose_blush open_mouth pencil ponytail ryuun_(stiil) sailor_collar school_uniform scrunchie serafuku shorts simple_background solo tears thighhighs translation_request trembling yellow_neckwear
1girl :d alcohol bird black_legwear blonde_hair blue_eyes brown_footwear cake champagne champagne_flute chicken child christmas_tree cross-laced_footwear cup drinking_glass fire food fruit gift grey_background highres holly hood little_match_girl matchbox matches matchgirl nou open_mouth ornament red_hood red_skirt shoumetsu_toshi_2 skirt smile snowflake_print solo strawberry thighhighs wreath
1girl black_legwear blonde_hair blue_jacket blue_sky blurry blurry_foreground boots character_name clenched_teeth cloud cloudy_sky commentary covered_eyes cross crying day depth_of_field english epaulettes field grass hair_over_eyes highres idolmaster idolmaster_cinderella_girls jacket long_hair long_sleeves military_jacket object_hug outdoors pantyhose pleated_skirt ponytail rheez seizon_honnou_valkyria sitting skirt sky sobbing solo takamori_aiko tears teeth tombstone wariza white_footwear white_skirt
1boy 1girl ^_^ admiral_(kantai_collection) amputee ashtray bandaged_head bandages closed_eyes comic crying facial_hair fang greyscale hair_ornament hairclip highres ikazuchi_(kantai_collection) kantai_collection monochrome neckerchief school_uniform serafuku shaded_face short_hair smile smoke smoking stubble sweat tears translated wave_(world_wide_wave)
... absurdres animal_ears forest half_moon highres kasodani_kyouko moon nature rakugaki-biyori spoken_character spoken_ellipsis tears touhou tree
1girl admiral_(kantai_collection) blood bra brown_hair gloves hair_ribbon jet_yowatari kantai_collection military military_uniform naval_uniform navel_cutout pink_bra ponytail ribbon school_uniform serafuku shikinami_(kantai_collection) short_hair short_ponytail tears torn_clothes underwear uniform water
1629doyasa 2girls absurdres animal_ears comic common_raccoon_(kemono_friends) crying dying fennec_(kemono_friends) fox_ears fur_collar greyscale highres kemono_friends monochrome multiple_girls raccoon_ears raccoon_tail short_hair sick tail tears translation_request