Each time the loop resets, the situation grows darker. Damon initially believes he can "solve" the loop by being a hero, but the Stone reveals that his true torment is his repressed guilt regarding his mother, Lily.
Following his death in the mid-season finale, Damon's soul is trapped inside the , a mystical artifact that forces vampires to relive their personal hells. [S7E10] Hell Is Other People
The title is a direct reference to Jean-Paul Sartre’s 1944 play, . Each time the loop resets, the situation grows darker
"The Vampire Diaries" Hell Is Other People (TV Episode 2016) Each time the loop resets