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Danbooru

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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", ect.) unless you can see why that hurts.

See also:

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

1boy 1girl absurdres braid bridal_veil bride comic couple dress elbow_gloves glasses gloves hetero highres kirisame_marisa monochrome morichika_rinnosuke short_hair tears touhou translated veil wedding wedding_dress yumiya

comic hairband hong_meiling izayoi_sakuya minakata_sunao monochrome short_hair touhou translated

:> backpack bag comic eyes getter-3 getter_robo hat highres iwatobi_hiro kawashiro_nitori monochrome moriya_suwako nobiiru_arm o_o robot robotic_arms seiza short_hair sitting tears touhou translated trembling twintails

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 plaid plaid_skirt plaid_vest red_eyes sad short_hair skirt skirt_set tail team_9 tears touhou translated tsuki_wani tsurime v_arms wings

absurdres apron aya_shachou blonde_hair blue_eyes brown_hair closed_eyes comic discrimination graffiti highres kiss maribel_hearn naked_apron red_eyes sad source_request touhou translated usami_renko yuri

1girl aqua_hair bow bowtie cast cirno closed_eyes eyepatch oekaki open_mouth samanda short_hair solo touhou translated ⑨

:d >_< alice_margatroid bad_id blonde_hair blue_eyes boots character_doll crying doll doll_hug hakou_(barasensou) hand_on_head holding hug kirisame_marisa lonely m-1_grand_prix open_mouth outstretched_arms petting sad shanghai_doll simple_background sitting smile spread_arms tears touhou translated wariza xd

absurdres arrow bad_id blood comic highres hong_meiling injury inu_tsuki izayoi_sakuya monochrome tears touhou translated yuri

1girl no_hat no_headwear saigyouji_yuyuko saigyouji_yuyuko_(living) short_hair solo tears touhou translated viva!!

0_0 1girl blue_hair blush bow cirno kuromame_(8gou) letter sad solo tears touhou translated wings

absurdres alternate_costume blonde_hair colored_eyelashes contemporary detached_sleeves english eyelashes frog green_hair hair_ornament hat highres kochiya_sanae moriya_suwako pants purple_hair rope sad school_uniform 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

brown_hair bus dante_alighieri english hal_(artist) motor_vehicle original school_uniform serafuku truth vehicle

1girl animal_ears blush detached_sleeves fang galbany_(tsgororin) green_eyes inubashiri_momiji peeking_out short_hair silver_hair solo tears touhou translated trembling wolf_ears

2girls absurdres bad_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

blood cherry_blossoms death from_above hal_(goshujinomocha) knife letterboxed lying on_back perfect_cherry_blossom pink_hair saigyou_ayakashi saigyouji_yuyuko saigyouji_yuyuko_(living) short_hair suicide tears touhou tree umbrella yakumo_yukari

2girls absurdres commentary_request death fujiwara_no_mokou highres kamishirasawa_keine long_image multiple_girls old smoke tall_image tears touhou translated yumiya yuri

alice_margatroid animal_ears baibo 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_tails perfect_cherry_blossom pink_hair saigyouji_yuyuko shanghai_doll short_hair tail touhou yakumo_ran yakumo_yukari

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