Damon typically does not reveal much of what’s happened in his life, but there’s one scene where he talks about how he came to be the way he is. It’s very intimate. Damon did something that’s exceptionally dark.
— Does Damon open up to his girlfriend Elena about his horrific history?
DAMON’S PAST RETURNS TO HAUNT HIM — Damon (Ian Somerhalder) realizes Elena (Nina Dobrev) is in danger and enlists Stefan’s (Paul Wesley) help to find her. The brothers pay a visit to Aaron (guest star Shaun Sipos), and Damon shocks Stefan by revealing his first-hand knowledge of Aaron’s family. In an attempt to stop Damon, Dr. Wes (guest star Rick Cosnett) unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes’ confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine (Nina Dobrev) turns to Matt (Zach Roerig) for help, until she realizes that Nadia (guest star Olga Fonda) may be the one who can solve her problem.
— the official synopsis for The Vampire Diaries: Fifty Shades of Grayson (EP510)
FLASHBACKS TO A DARK TIME IN DAMON’S LIFE - Stefan continues to offer Katherine his support while trying to mask his own pain, until Caroline shows up with an unusual form of therapy. After trying to make amends with Caroline, Elena grows so concerned about Damon that she turns to Aaron (guest star Shaun Sipos) for help. Later, when Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades, she shares the disturbing information she just learned about her own family. Finally, Aaron decides on a desperate course of action after a conversation with Dr. Wes (guest star Rick Cosnett).
— OFFICIAL SYNOPSIS FOR THE VAMPIRE DIARIES: THE CELL (EP509)
Damon might be secretly concerned about his girlfriend’s pull to her ex/his brother, but the question remains: Does Stefan even want to be with Elena right now? “I think their love has faded,” admits Paul Wesley. “It’s dissipated.
— Vampire Diaries Stars Talk Delena ‘Tension,’ Stelena’s ‘Faded’ Romance x