|“||I hate you because you could've come back so many times, but you never did. I lost you the first time when Father sent you away with consumption, and then we brought you back from this prison world, and then I lost you again to your other family. And now, I'm losing you to death. Three times, I lost you. Three times, I had the chance to tell you everything I want to tell you, and three times I ruined it.||”|
The mother-son relationship between the vampires Lillian Salvatore and Damon Salvatore. In modern times, their relationship is severely strained even after Lily's final death (as a vampire). However, when Damon is put into the Phoenix Stone to suffer hell, he comes to regret his goodbye to Lily before she died. Damon, deep down, misses Lily even though he may still refuse to admit it.
Damon is Lillian's first child and her oldest son with Giuseppe. Lily had consumption and had become very sick, to which Giuseppe sent her away. Damon knew that his mother died in 1858.
Throughout The Vampire Diaries Series
In Let Her Go, Bonnie tells him she was in his house in 1903 in the prison world. She still had her camcorder on and plays it for him. Damon sees the woman Bonnie saw. It's his mother and he discovers that his mother is alive.
In The Downward Spiral, Damon along with Kai go to The Salvatore Crypt to break open his mothers coffin. Damon tells Kai that his mother died and that wasnt her in the recording in Bonnies camcorder in the 1903 prison world. Kai tells Damon that it's is possible if she is a vampire. Damon finally breaks open the coffin to see no one is in there. He realizes now it's possible his mother is a vampire. Damon asks Kai to send him to the Prison World so he can get his mother out, later on Kai refuses, he reveals to Damon that Lily is a Ripper. Kai then tells Damon that she and the heretics were captured and sent to the 1903 prison world, similar to him. Kai also mentions that Lily has killed thousands of people. Damon ddoesn't want to hear anymore he demands Kai to shut up.In A Bird in a Gilded Cage, Damon and Elena go to the 1903 prison world to bring back his mother. Once Damon is done swearing that his mother is dead to him, she arrives. Lily serves Damon and Elena tea and explains her life. She drained all the blood nearby and now survives on two drops a week. When laughs when Damon tells her that Stefan ripped their father's throat out. When Lilly admits she hated her husband, Damon guilt's her for leaving him and Stefan with him. After Damon and Elena explain the need to turn Stefan's humanity back on, she agrees. Then she mentions her "traveling companions". She introduces them to a table full of mummified vampires. Lilly explains the mummified vampires saved her from herself and her ripper tendencies. She says they gave up their blood rations for her and she learned to control her blood lust. Damon thinks she's wackadoodle. When Lilly goes to get the last of the blood to revive them, Elena notices the ascendant is on the table. Damon tells Elena that Bonnie isn't looking for the ascendant. As the aurora borealis begins, Bonnie joins Damon and Stefan. When Damon explains to Lilly that they're short one witch and her friends can't go, Lilly refuses. She insists that the vampires are her family and she won't leave without him, but Damon threatens to leave her, too. As Bonnie recites the spell, Kai arrives and watches Damon, Elena, Lilly and Bonnie disappear out of the prison world. Back at the Salvatore house, Lily admits to Damon that she did visit Stefan the night of her funeral. Stefan only remembers her as an angel. But when she leaned down to whisper in his ear, all she could hear was the pound of his blood, so she fled for their sake. She assures Damon she missed them twice as much as they missed her. When Lily asks again about getting her friends back, he assures her they'll be going back soon.
In I Never Could Love Like That, At breakfast, all Lily can talk about it returning to her prison world to get her friends. Lily casually brings up the fact of being human hinting that she heard Bonnie and Damon last night. Damon makes an angry gesture to his mother as Elena leaves. On the road to Whitmore, Damon tries to prepare his mom to talk to Stefan and bring his humanity back. She states that she overheard Damon and Bonnie talking about the cure. She knows he's afraid he'll lose Elena if he gives it to her. He tells his mother that she needs to give a performance of a lifetime because she claims that she wasn't coming back to America for Stefan and Damon like he thought. At Whitmore, Lily worries how she's supposed to connect with Stefan. Damon suggests she tell the story of how she came back to get them, but Damon realizes she wasn't coming to get them. Lily admits she's been struggling to reconnect with how it felt to be their mother. She explains her "new" family helped her find herself again, but she lost any feelings she had for her old family in the process. Damon calls Elena, who then suggests that Lily would just simply try lying to Stefan if they hope to get him back. Damon orders Lily to give it her best shot, but she was assurances that they'll go get her people. She points out he's lying to Elena by not telling her about the cure and he gives her the ascendant as assurance. Stefan and Caroline are interrupted at the bar when Damon and Lily walk in. Damon watches as she reacts the sweet sentiments he fed her earlier.
In Because, Lily and Enzo then arrive at the Boarding House and they walk inside, to which Bonnie leaves before she is caught. She tells him that Damon assured her all will be well, but Enzo tells her Damon isn't the most trustworthy and leaves her concerned. She becomes furious as the Ascendant isn't in the drawer anymore and asks Enzo if it is entertaining that the Ascendant is gone and that it was the only thing that could rescue her family. She is talking to Damon on the phone and asks where the Ascendant is. He tells her and he tells her he doesn't have it. She thinks he is lying and she promises that she can easily destroy something of great significance to him. She then reveals that she has the cure and he says she wouldn't do it. She threateningly tells him to bring her the Ascendant or she will crush the cure with her own hand. She is seen standing in front of the fireplace with the cure in one hand and a poker to stoke the fire. Damon arrives and she asks if he has the Ascendant. He tells he doesn't because he doesn't have it and she tells him that he understands what's going to happen next. She drops the box into the fire and Damon walks toward her with wide eyes surprised at what she did. She tells him she did him a favor and the sense of relief that he feels right now means Elena will never leave him. Elena walks into the room and Lily answers for Damon saying that what she has right now is the cure for vampirism and she left it out for her as Damon was never going to offer it to her. Elena is hurt and confused, and Damon tells her he can explain, to which Lily says it looks like they have a lot to talk about.
In I'd Leave My Happy Home For You, Lily snaps Damon's neck, leaving Elena human and alone with her. At the Grill Lily charges Stefan to attack, but Damon injects her with vervain.
In Day One of Twenty-Two Thousand, Give or Take, Damon noticed that Lily's Heretic family are chaos added to Mystic Falls. Damon allies with Stefan as his younger brother makes a plan, with Caroline Forbes and Matt Donovan, in order try and kill the Heretics. After Stefan, Caroline and Matt build the bomb to try and blow up all the Heretics, Lily's Heretics are livid and seek revenge. The Heretics decide to massacre everyone at Matt's police academy graduation, leaving a bloodbath in their wake. Lily shows up after the massacre and scolds all her children, the Heretics and her sons. Damon is forced to help evacuate the town of Mystic Falls in order to keep the town safe. Stefan and Lily then create a treaty: Lily and her Heretic family get to live in the Salvatore Boarding House while Stefan and Damon stay at Tyler Lockwood's home. This enrages Damon. The treaty between the Salvatore's and the Heretics also explains that the Heretics can only feed on humans who cross Mystic Falls' boarders, but they cannot attack outside its boarders. In return, Stefan gives up his ownership of the Salvatore Boarding House. This episode marks Damon's hatred and rivalry against his own mother and her adoptive "children," the Heretics. In Never Let Me Go, when Malcolm, one of the Heretics, is murdered by Damon (with the help of Bonnie), this threatens negotiations between the Salvatore's and the Heretics. As revenge, Lily and her adoptive family steal Elena's coffin and kidnap Stefan's girlfriend, Caroline. Stefan attempts to right the wrong on his side of the treaty (between the Heretics and the Salvatore brothers) by apologizing himself. Lily states that she doesn't want Stefan to apologize because it was all Damon's fault for killing Malcolm in the first place. Stefan asks Damon to apologize in order to help release Caroline from being held prisoner in the Salvatore Boarding House. Damon is stubborn at first, but he goes to Lily's home and says a bitterly sarcastic apology, which only worsens the negotiations between the two sides. However, this only worsens things between the Salvatore brothers and Lily.
In Age of Innocence, it is revealed that Lily would have taken Stefan and Damon away from her abusive husband and would have taken them away from Mystic Falls. This failed those years ago though. Damon states that he wasn't surprised. This changes nothing between Lily and Damon
In Live Through This, after Valerie helps Damon and Stefan find Lily's old lover's (Julian) body, she reveals that Julian is the one who killed Valerie and Stefan's stillborn child. Damon and Stefan later ally with Valerie in trying to burn his body before the rest of the Heretics try to bring Julian's soul back from the Phoenix Stone. Lily and her Heretic family stop the three of them from burning Julian's body. Lily is shocked and heartbroken that her sons, especially Valerie, would do this to her. Lily then reveals that it was her idea to let Kai put Elena in a sleeping coma. This angers Damon to the point when he begins to brutally strangle Lily. Beau, another Heretic, helps Lily by siphoning an explosion spell within the warehouse they all were caught in, while trying to either save or kill Julian's body. Damon, Stefan and Valerie are caught in the crossfire, but they aren't killed from it. Damon, Valerie and Stefan all agree that their fight against Julian and the rest of the Heretics wasn't over yet.
In Best Served Cold, Lily invites her sons to a dinner party welcoming Julian back from the Phoenix Stone. Damon and Stefan attend in order to see what Julian was like. However, both of them disagree on how and when to kill Julian. Damon wants to kill Julian later on to make Lily suffer, but Stefan wants to kill Julian quickly because of killing his unborn child. After Damon and Stefan get into a brutal fight and argument with Lily and Julian, Stefan tells the story about his miscarried child with Valerie and Damon finally agrees to help kill Julian as soon as possible.
In Mommie Dearest, in order to have Julian killed, Damon unwillingly helps Stefan to decide to try and convince their mother of Julian's manipulative ways. It takes an old memory of Lily's deceased husband to finally see that she has yet another man in her life abusing her and the ones she loves. Lily, at the end of the episode, sides with Damon, Valerie and Stefan in order to have Julian murdered.
In Hold Me, Thrill Me, Kiss Me, Kill Me, during Nora and Mary Louise's anniversary party, Stefan and Lily, along with Damon, are tasked with allying together to end Julian's life. When Damon and Valerie are captured by Julian, Julian tries to force Lily to choose between her biological family and her Heretic family. Refusing to choose, Lily stakes herself in the heart thinking that her life is still linked to Julian, which it wasn't. Damon, Stefan, and the rest of the Heretics are forced to watch Lily die a heartbreaking death. Stefan tries to convince Damon to say his goodbyes to Lily before it was too late, but Damon cruelly tells her that she made her bed and that he hopes she rests well.
- Damon thought that his mother died of consumption in 1858.
- In Let Her Go, Bonnie informs Damon that his mother Lily is still alive and trapped in the 1903 prison world.
- In The Downward Spiral, Kai reveals to Damon that Lily is a Ripper.
- In A Bird in a Gilded Cage, Damon and Elena go to the 1903 prison world to bring back his mother.
- Damon rescues Lily from the prison world to bring back Stefan's humanity.
- Damon's friend Enzo has romantic feelings for Lily.
- In Live Through This, Damon and Stefan find out that it was actually Lily's idea to link Elena's life with Bonnie which was executed by Kai in I'll Wed You in the Golden Summertime.
- Lily reveals to Stefan that, it was actually her not Damon who stole the money from Giuseppe's bureau so that she could buy tickets to escape with her sons.
- Damon was punished by Giuseppe because he thought he stole the money.
- Lily stakes herself to save Damon and kill Julian along with her without knowing the fact that Mary Louise already unlinked her from him.
- Damon hallucinates about Lily when he got affected by Werewolf venom by the Huntress.
- Despite his harsh words to Lily after she chose the Heretics over him and Stefan, Damon truly did love his mother. During his time in the Phoenix Stone, he finally broke down and admitted that he missed her, and that he wanted to be a better son to her.
Damon about Lily "She tossed us aside without any concern of what would happen to us. As much as I'm concerned, she deserves what she gets. she deserves what she gets"