Upon waking, Damon is so traumatized that he believes he is still in a loop. He lashes out and seemingly kills Bonnie, Caroline, Matt, and Stefan, leaving the episode on a massive cliffhanger. Philosophical Roots
Damon only escapes after finally submitting to his pain and expressing genuine remorse to a vision of his dying mother. [S7E10] Hell Is Other People
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. Upon waking, Damon is so traumatized that he