Relationships

This section will focus on some of the key interactions or relationships that come up in the books and how this gives us more insight into Damon and how he operates.

His Mother

Although Damon and Stefan's mother never appears in the books, she is spoken of when Stefan reveals his history to Elena and we learn that she has played an important part in the formation of the relationship between the two brothers, and also between Damon and his father.
Stefan tells Elena, that their mother died when he was very young - and that he believes that her death sparked resentment in Damon with whom he was very close. From what Stefan indicates he believes that this fueled, if not caused, the rift between them, as Damon blames Stefan for their mothers death. During the conversation with Elena near the end of The Awakening, Stefan explains that after his birth, their mother never fully recovered from the pregnancy. According to Stefan, Damon and their mother were very close, and Stefan felt that Damon blamed him for their mothers death. As Damon got older, other reasons would have compounded on this to fuel the hatred.
Nothing else was mentioned in the books about Damon's relationship with his mother, nor does Damon make any reference to it. We can only assume that this was an important turning point in his life.

His Father – Conte Giuseppe di Salvatore

Damon's father is a character that we only meet through Stefan's flash-backs during VD1. He is obviously a proud aristocrat who works for the benefit of Florence and expects the same from both of his sons. From the one flash-back where Damon has told his family of his intent not to return to University we can see that the relationship between father and son is tense, and has been for quite some time.
Damon and Stefan's father seems to be at the end of his patience with his son, and Damon gives his father little love or respect. Due to the time, we can assume that Guiseppe left the care of his sons up to nurses and servants, meaning that the pair would never have been close, and perhaps the death of their mother would not have helped.
The impact of Stefan's presence on the relationship between Damon and his father would have been important. Stefan seems to be prepared to follow in his father's footsteps, therefore being the counter of Damon, someone who will achieve what he would not, and Damon may have felt that his father cared more for his younger brother than him.

His Brother – Stefan Salvatore

The Vampire Diaries are narrated primarily from Stefan and Elena's perspectives in VD1-3 and then Bonnie in VD4, meaning we can never get a good idea of what Damon's thoughts are. But the books themselves give us the most insight into the relationship between the two brothers. From early in the series, we are informed that Stefan has a brother, and they are not on good terms. In fact there is a primarily one-sided hostility. One of the main reasons that Stefan left Italy was his loathing of the darkness in which Damon seems to have rejoiced. During his life, Stefan stayed in darkness, believing that he belonged there. Stefan tells Elena that Damon was part of his own gang and threatened him with death several times.
Stefan also speaks of his confusion at why his brother is so hostile towards him, but directs one of the causes to his mothers death which is further fueled by the death of Katherine.
The rivalry and hatred between them is rather one-sided – Damon keeps the hatred going, and often pushes Stefan into corners he would rather not be in. Damon sees Stefan as the weak and purer brother – he calls him 'little brother' with scorn and insults Stefan in front of Katherine and Elena questioning why they would choose the ‘weaker brother’ over himself.
Stefan tries to give Damon ‘chances’ to redeem himself, and always feels let down when nothing comes from them. The key point during the series is in VD4 when Damon offers to take watch at Vicki Bennett’s house, which surprises the entire group. Stefan agrees to this. However, when they come back they find that Vicki has been murdered by Klaus – and that Damon let him. Stefan is infuriated about this, blaming himself because he trusted Damon. Later we learn that, Damon couldn’t have stopped Klaus because he couldn’t get into the house. This shows us that Stefan wants to trust Damon. It is for the same reason that when Damon came back to Fell’s Church, Stefan urged the others to give Damon a chance to prove himself.
While there are extreme moments of animosity between the brothers, for example when Damon has actually threatened physical violence on Stefan – such as in the forest during VD4, Damon will always fall back into the protective older brother when it is really needed. This is despite Damon's often searing hatred and willingness to break Stefan’s heart in matters of love. The two key instances are with Katherine in VD3, when rather than killing Elena and Stefan, Damon would allow violence to himself, and in VD4 when Damon comes to the rescue of Stefan from Klaus.
At the end of Dark Reunion, Damon and Stefan's relationship is still strained, however, Stefan makes a move to include Damon in their celebration. Damon refuses the offer, but LJ Smith leaves the reader believing that Stefan at least has let go of his hatred for his brother.

Elena Gilbert

As with all of Damon's romantic interests, it is difficult to pick what his intentions were. But of all the female interests in the books, Damon does show that his feelings for Elena, were more than just an easy way to annoy his brother.
Damon was watching Elena before she and Stefan met. During The Awakening, Elena notices a large crow outside her house, watching her. Later, we learn that one of Damon's animals to call is the crow, implying that Damon was the crow outside Elena's house, Damon therefore perhaps forming an interest in Elena, before Stefan. In VD3, Katherine says that she brought the brothers to Fell’s Church because she thought the sight of Elena would make them feel guilty for what they did to her.
Damon, like Stefan shows interest in Elena – and again you are left wondering if Damon had a serious attraction to her or if it was just a way of hurting Stefan. Or perhaps, she did remind him of Katherine.
Damon seems to understand her passion, and challenges her more than Stefan does, and he uses this to try and claim her. For her part, Elena does feel some affinity to Damon and his own dark power, as if he recognises something in her that the others do not. During the scene where Elena and Damon rush to rescue Stefan from the towns-folk, Elena notes the power as they work as a team.

Klaus

A relationship that was hardly expanded on. We know Klaus and Damon met outside Vicki Bennett’s house when Damon was guarding her. From the argument that followed when Stefan returned to find Vicki dead, we can assume that Damon had some kind of conversation with Klaus and 'let' him get to Vicki and kill her. However, from watching Damon throughout the books, it is unlikely that Damon just let Vicki’s murder take place, so there must have been some engaging. During the argument Damon tells Stefan that he does not know what he is dealing with and that it is out of both of their leagues.
It does seem like Klaus 'let' Damon go unharmed, when Damon comes to the clearing to help Stefan, Klaus reminds him that they could just ignore each other if Damon let Klaus do as he wished. In some ways it seems that Klaus was trying to appeal to Damon’s sense of the hunter, that Damon should turn a blind-eye to the murder of Vicki and then Stefan as it was all just part of the game. This could be another reason that Damon let Klaus get to Vicki, as he knew she was prey and eventually would be caught. But even if this is true, Klaus eventually over-steps the mark by attacking Stefan.

His Maker - Katherine von Swartzschild

The daughter of his father's friend, Katherine initially showed interest in Stefan, and according to Stefan, their parents were speaking of marriage between the two. But when Damon returned from University, Katherine quickly became interested in him too. From what we can gather, Katherine must have been quite taken with Damon, as on an early evening when he returned from University, she left dinner with Damon rather than Stefan. But also, she revealed her secret to him, quite quickly, indicating some level of trust with Damon.
We can not gather much of their relationship, as the flashbacks don’t give us much indication of what kind of relationship it was. But in VD3, Katherine says to Stefan that she loved him best.
From Damon’s perspective as well, we can not tell if he really had an interest in Katherine or if it was just a way to hurt his brother. However, Damon was angered when, after finding Katherine’s ashes, Stefan made a grab for her ring. Could it be that he did have some feelings for her?
When Damon finally finds out that Katherine never did kill herself, that it was all just a ploy to try and get Damon and Stefan together, he isn't surprised by the fact that she is alive, like Stefan was. Actually, he seems amused, either at Katherine's clever plot, or at their folly.

Bonnie McCullough

Damon and Bonnie first met at the party that Alaric Saltzman held at his house in VD2. She later gushes to Elena about how gorgeous he is. Bonnie is a girl that seems to fall in and out of love easily and enjoys just looking at cute boys and having a fun time.
During VD3 and VD4 we are thrown several hints from the author that there is some attraction between Bonnie and Damon. Certainly on Bonnie’s part, she remarks about how cute Damon is – particularly after the incident at Alaric Salztman’s house. Damon shows some interest in Bonnie during VD4 – outside Vicki's house where he has nearly seduced her before Matt interferes. However, even then, Damon taunts Matt with the fact that he is a hunter and has needs.
So like many of Damon’s interests, you are left wondering – is Damon for real or is this just another of his conquests? Even Bonnie, after Damon leaves in VD3 points out that he is dangerous, and just one of those guys you look at from afar rather than go after.
For my part, and I mention this in the questions section, I feel that although there was some attraction between them, it was merely Damon going for another conquest. He was a hunter, and she the prey. Even from Bonnie's side, I do not see her interest going beyond that of admiration.

Matt Honeycutt

While not one of the key relationships during the series, the interaction between Matt and Damon was an interesting one, beginning with a mutual dislike – especially on Damon’s part, seeing Matt as just another source of food and amusement, but then ending with some sort of begrudging respect on both sides. Matt and Damon had their first key interaction during The Fury when Elena needed blood to keep her alive after waking. During this time Damon showed clinical efficiency in pointing out where to take blood from him. This event proved to be for Matt, himself, a turning point, and his character became far more depressed and thoughtful of the ‘darker side’ of life.
But Matt and Damon had no real interaction until VD4 when they met up again. It was during VD4 that Damon actually paid any attention to Matt, who showed himself to be a protector of Bonnie, whom in turn, Damon seemed to show some interest in – Matt was in his way. During one of the watches on Vicki, Damon made a play at Bonnie, only to be interupted by Matt. A confrontation took place between Matt and Damon, where Matt refused to back down in the face of Damon’s threats. This earned a respect from Damon, and when Damon backed down, Matt was curious why he had done so. It was this curiosity that made him re-think why Damon didn’t go to the help of Vicki Bennett. And at the end of VD4, Matt offers Damon the chance to join the group in celebration. Despite Damon refusing the offer, there seemed to be either an understanding or respect between the two characters.