When Day Breaks, You'll Come Back

Short Tragic Stories That'll Make Even Someone with a High Tear Threshold Cry

Historical or modern settings are both fine.

Angsty Short Stories That’ll Leave You Sobbing at Midnight

Angsty Stories: Short and Heartbreaking, Enough to Make Your Eyes Swell from Crying!

Something short, not an overly long tragic story.

Short Stories, Bad Endings, The Kind That Leave You Crying Yourself to Death at Midnight

Tomato Novel's Four Great Tearjerkers

I want to read something similar to He Sinian, I Finally Found the Courage to Leave. Which of these three should I add?

Got a Pebble in My Eye. Give Me a Tearjerker to Make Me Cry

It has to be really, really angsty, preferably starting right from the first or second chapter.