Pool: Soul-Crushingly Depressing

Pictures whose depressing nature hurt you deep down inside. Pictures that make you cry.
Pictures that are on par with the movie Grave of the Fireflies.
black_hair closed_eyes desk hirasawa_yui imagining k-on! kotobuki_tsumugi long_hair monochrome nakano_azusa school_uniform sepia sorasou_torikodan tainaka_ritsu tea twintails rating:Safe score:2 user:danbooru box cardboard_box for_adoption in_container kokenyan nintendo no_humans pichu pokemon rain sad tears rating:Safe score:1 user:Gelbooru alternate_hairstyle android aqua_hair bad_id blush damaged detached_sleeves flower_pot hatsune_miku hello_planet_(vocaloid) highres long_hair necktie nuko_(mikupantu) open_mouth rust sad severed_arm severed_limb sitting skirt tears thighhighs translated translation_request very_long_hair vocaloid wariza rating:Safe score:0 user:Gelbooru blonde_hair can cat cigarette durarara!! heiwajima_shizuo male road_sign shiwasuda short_hair sign snack snacks solo rating:Safe score:3 user:Gelbooru barefoot naoi_ayato oekaki otonashi_(angel_beats!) otonashi_hatsune siblings spoilers takumi_(pixiv415088) takumi_(scya) translation_request yuri_(angel_beats!) rating:Safe score:1 user:Gelbooru aragaki_shinjirou beanie blood comic monochrome persona persona_3 persona_3_portable segami_daisuke tears translation_request trenchcoat rating:Safe score:0 user:Gelbooru blue_hair heterochromia rain red_eyes sho_(pixiv) short_hair solo tatara_kogasa touhou translated umbrella rating:Safe score:0 user:Gelbooru animal_ears baby bad_id breath comic empty_eyes gloves highres long_hair monochrome silent_comic spot_color touhou umbrella wimifu yakumo_ran yakumo_yukari rating:Safe score:2 user:Gelbooru bed blood death green_eyes helmet highres lips mole nervegear nosebleed sachi_(sao) short_hair simple_background solo spoiler spoilers sword_art_online tears white_background rating:Safe score:1 user:danbooru breastplate christmas closed_eyes elbow_gloves eyes_closed gloves highres sachi_(sao) short_hair snow snowing solo sword_art_online tears tree wallpaper waving winter yuuri_(asterisk) yuuri_nayuta rating:Safe score:2 user:danbooru 1girl armor black_hair blue_eyes blue_hair blush closed_eyes coat crystal elbow_gloves eyes_closed facepalm fur_trim gloves highres hug hug_from_behind kazuna kirito letterboxed sachi_(sao) short_hair smile sword_art_online tears rating:Safe score:0 user:danbooru 1girl armor belt black_hair blue blue_eyes blue_hair cape coat covering_eyes cry elbow_gloves fur_trim gloves hug kirito mole sachi_(sao) senri_(ho_ru03_15) smile sword_art_online tears rating:Safe score:1 user:danbooru 1girl blood blood_on_face blood_stain bloody_clothes breast_pillow breasts brown_hair carrying code_geass death dress euphemia_li_britannia formal high_heels hug kneeling kururugi_suzaku long_hair one_knee pink_dress pink_hair princess_carry r0c shoes short_hair simple_background spoilers white_background rating:Safe score:2 user:danbooru black_hair blonde_hair blue_eyes blue_hair blush brown_hair c.c. cap closed_eyes code_geass couple euphemia_li_britannia everyone gino_weinberg glasses green_eyes green_hair hair_ribbon highres kallen_stadtfeld kimura_takahiro kururugi_suzaku lelouch_lamperouge long_hair milly_ashford necktie nina_einstein nunnally_lamperouge panties pantyshot pink_hair red_eyes red_hair ribbon ricca rivalz_cardemonde rollo_lamperouge rolo_lamperouge school_uniform seifuku shirley_fenette short_hair sitting skirt smile striped striped_legwear sumeragi_kaguya thighhighs underwear v very_long_hair wallpaper rating:Safe score:3 user:MoeImouto