Dear Esther is a game about loss and grief, so naturally there are some heartbreaking moments you'll come across as you travel around the island.
- The narrator lost his wife in a car accident. That part never changes, no matter the differences in each playthrough.
- Some of the variations can make things worse. For example, sometimes the driver was a man named Paul, who could either be drunk or not drunk at all. But sometimes, it's the narrator who was the drunk driver.
- And sometimes the game implies that Esther was pregnant when she died. One of the possible bits of randomization the game can do is making an ultrasound picture appear in certain places. It makes the implications of Esther's death even heavier and more hard-hitting to consider.
- The big Wham Shot- after falling into one of the underground pools, you find yourself underwater, floating around the scene of the car accident that took Esther away from the Narrator.
- Though sometimes it's also an operating table, perhaps as a reference to the time the narrator had kidney stones.
- Some of the variations can make things worse. For example, sometimes the driver was a man named Paul, who could either be drunk or not drunk at all. But sometimes, it's the narrator who was the drunk driver.
- The narrator is obviously severely depressed in every letter you hear. No matter how he got there (by accident or on purpose) it's clear he intends to die on this island.
- Every time you fall down a hole or go too far into the water (except in the caves), you are pulled back while hearing the narrator softly chant "come back". The ending has the narrator chant it once more, but now also saying Esther's name. The narrator wasn't trying to bring you back- he wants Esther back.
- Jakobson's fate. Jakobson dies trying to climb back up the mount, and most of the time his body isn't found until spring.
- The narrator starts to sound more and more insane the closer you get to the aerial, babbling and blurring everything he's mentioned before together. Even if you're confused over what's happening, you can't help but pity this poor guy on the verge of a breakdown.
- The ending. You jump off the aerial and take flight. If Surprisingly Realistic Outcome is in effect here, then the narrator jumped to his death in order to be with his beloved Esther once more.
