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 cirno closed_eyes hanada_hyou letty_whiterock multiple_girls petting profile silhouette snow touhou wings
1girl ascot closed_eyes flower from_above gatau green_hair kazami_yuuka lonely plaid plaid_skirt plaid_vest red_eyes short_hair skirt skirt_set smile sunflower sweatdrop touhou translated v_arms vest
1boy 1girl absurdres bare_shoulders bow braid bridal_veil bride collarbone comic couple crying dress elbow_gloves glasses gloves hair_bow hetero highres kirisame_marisa long_image looking_at_another looking_down looking_up monochrome morichika_rinnosuke nose petting profile sad short_hair tall_image tears touhou translated veil wavy_mouth wedding wedding_dress window yumiya
2girls comic doujinshi greyscale hairband hong_meiling izayoi_sakuya minakata_sunao monochrome multiple_girls short_hair touhou translated
+++ 2girls :> backpack bag comic crying eyes getter-3 getter_robo greyscale hat highres iwatobi_hiro kawashiro_nitori mechanical_arm monochrome moriya_suwako multiple_girls nobiiru_arm o_o robot seiza short_hair sitting tears touhou translated trembling twintails
4girls animal_ears ascot blue_hair blush bow breast_squeeze breasts brown_hair bunny_ears cat_ears cat_tail chen cirno comic green_hair highres inaba_tewi kazami_yuuka lonely medium_breasts multiple_girls plaid plaid_skirt plaid_vest red_eyes sad short_hair skirt skirt_set tail team_9 tears touhou translated tsuki_wani tsurime v_arms vest wings
2girls absurdres apron aya_shachou blonde_hair blue_eyes brown_hair closed_eyes comic discrimination graffiti highres kiss long_image maribel_hearn multiple_girls naked_apron red_eyes sad source_request tall_image touhou translated usami_renko yuri
(9) 1girl aqua_hair bow bowtie cast cirno closed_eyes eyepatch oekaki open_mouth samanda short_hair solo touhou translated
2girls :d >_< alice_margatroid bad_id bad_pixiv_id blonde_hair blue_eyes boots character_doll closed_eyes crying doll doll_hug hakou_(barasensou) hand_on_another's_head holding hug kirisame_marisa lonely m-1_grand_prix multiple_girls open_mouth outstretched_arms petting sad shanghai_doll simple_background sitting smile spread_arms tears touhou translated wariza xd ze_(phrase)
2girls absurdres arrow bad_id bad_pixiv_id blood comic greyscale highres hong_meiling injury inu_tsuki izayoi_sakuya long_image monochrome multiple_girls tall_image tears touhou translated yuri
1girl commentary crying crying_with_eyes_open no_hat no_headwear saigyouji_yuyuko saigyouji_yuyuko_(living) short_hair solo tears touhou translated viva!!
0_0 1girl bad_id bad_pixiv_id blue_hair blush bow cirno kuromame_(8gou) letter sad solo tears touhou translated wings
3girls absurdres alternate_costume blonde_hair colored_eyelashes commentary contemporary detached_sleeves english eyelashes frog green_hair hair_ornament hat highres kochiya_sanae long_image moriya_suwako multiple_girls pants purple_hair rope sad school_uniform serafuku tall_image tears touhou traghetto yasaka_kanako
2girls blonde_hair blue_eyes cherry_blossoms elbow_gloves gloves hairband hat konpaku_youmu kouzilow long_hair multiple_girls short_hair silver_hair tears touhou yakumo_yukari
1girl brown_hair bus comic dante_alighieri english ground_vehicle haruo_(clownberry) motor_vehicle original school_uniform serafuku truth
2girls absurdres bad_id bad_pixiv_id blonde_hair blood closed_eyes death hair_over_eyes highres hug long_hair multiple_girls no_hat no_headwear pink_hair saigyouji_yuyuko saigyouji_yuyuko_(living) tears touhou very_long_hair windyakuma yakumo_yukari
2girls blood cherry_blossoms death from_above hal_(goshujinomocha) japanese_clothes kimono knife letterboxed lying multiple_girls on_back perfect_cherry_blossom pink_hair saigyou_ayakashi saigyouji_yuyuko saigyouji_yuyuko_(living) short_hair suicide tears touhou tree umbrella yakumo_yukari yukata
6+girls alice_margatroid animal_ears blonde_hair brown_hair cat_ears chen cirno doll dress fox_tail hairband hat japanese_clothes konpaku_youmu letty_whiterock lily_white lonely long_hair lunasa_prismriver lyrica_prismriver merlin_prismriver multiple_girls multiple_tails paipo_(chickshow) perfect_cherry_blossom pink_hair saigyouji_yuyuko shanghai_doll short_hair tail touhou yakumo_ran yakumo_yukari
1girl blush bow chaigidhiell confession crying crying_with_eyes_open face fujiwara_no_mokou hair_bow long_hair open_mouth pov red_eyes sad silver_hair sobbing solo tears touhou translated
1girl bags_under_eyes commentary_request depressed hat izayoi_sakuya maid profile ribbon seki_(red_shine) sitting solo tears touhou white_background
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