Hey people! Kay, so this is just a Damon one-shot, because we all know that he secretly cares but he just wants to hide it by drowning himself in bourbon and firing sarcastic comments... So yeah, this is it! :D
Damon prided himself in not caring about anyone besides himself, although he sometimes allowed himself to make the occasional exception. Admittedly, he knew that for someone who possessed a devil-may-care attitude such as himself, he'd made several exceptions too many.
He was okay with making an allowance for Stefan every so often, but come on; Stefan was his little brother after all. He remembers when he tore Mason Lockwood's heart from his chest, and how Katherine had compelled Jenna to stab herself as a way of expressing her distaste. Of course, being the self-sacrificing martyrs that they were, Elena and Stefan were only too quick to put all of the blame on their own shoulders and not even consider the thought that maybe he had played a major part in winding up the conniving bitch. Elena had broken up with Stefan and then hurried out the door, only sparing a moment to turn back and tell the guilt ridden older brother that 'she'd won; Katherine won'. That left Damon alone with his little brother, who he found stood in the centre of the living room, tears trickling down his distraught face. Damon had forced his mouth into a reassuring, yet faint, smile, had poured out two glasses of bourbon and handed one to his brother. He'd sat next to him on the couch through to the early hours of the morning, a hand on the younger man's shoulder, both as a means of saying 'it's okay' and 'I'm sorry' without having to utter a word. He'd bitten back any sarcastic comment that threatened to spill over the surface, and he'd been painfully aware of just how much Stefan's teen drama bothered him. He cared way to much than he would've liked to.
He'd never give a damn about Katherine again, after all that the manipulative bitch had put him and his brother through. It seemed, however, that her actions just led to him giving a damn about someone else. That was probably why he had a sort of soft spot for Caroline, the neurotic vampire Barbie who, although indisputably annoying, had her heart in the right place. He put up with her incessant whinging, and during the catastrophe known as 'Liz found out – take one', he'd felt the need to defend her to her vampire hating mother. Liz had asked him to keep Caroline away from her. With only a moment's thought, Damon had replied with 'she's your daughter, Liz', as if that resolved the whole situation. And in his mind, it did resolve the whole situation. Family was important. When Liz had insisted that Caroline wasn't her daughter anymore, Damon was sure to convince her that she couldn't be more wrong. Damon really hated feeling weak, and caring for his very own messed up Scooby doo gang of teenagers made him feel just that.
He got on with Jenna okay as well, winning over her numerous death glares by making dinner and bringing endless bottles of alcohol over as a way of saying 'don't hate me, I'm awesome'. That was up until when events had taken a dramatic turn for the worse. No, a turn didn't cover it; their little airplane of events had been taken by surprise in a fatal patch of turbulence, and that good little plane had fallen into a nose dive and crashed into the ground. Jenna had died, and they hadn't been able to stop it. Damon didn't feel like joking after that, but he knew he had to pretend he didn't give a damn so that Elena and Jeremy could get on with their lives with one less person shooting them the sympathy glance. He'd hated getting that look after his mother had died, so it was all he could do not to subject the Gilberts to the same treatment.
He was more than happy to spend an evening getting wasted at the grill alongside his drinking buddy and badass-vampire-hunting-modern-day-Giles-partner-in-crime, and when he'd find out that he'd turned the guy's wife, he'd actually felt a little sorry for the other man. He felt even sorrier still after Klaus had killed Jenna, seeing how broken the history teacher now was, and guiltier still when he realised that Ric kinda blamed him in this. Damon knew he did the right thing though, by having Bonnie cast a spell to keep Ric out of the action. If he knew he did the right thing, then why did he still care so much?
Sometimes, Damon found he even cared a little for the judgey witch who liked to burst his brain whenever she got bored of his, to be quite honest, amazing sense of humour. He kind of owed her; after all of the times she'd agreed to help them out. She'd helped them with Mason Lockwood, with trying to kill Katherine, on countless 'save Elena' missions… without her; they would probably have lost Elena several months back. Damon told himself that he only cared about Bonnie because she was helpful, and he forced himself to believe that.
If that wasn't shocking enough, he even found a part of him that felt something for that whiny emo punk that was Jeremy Gilbert. That kid reminded him of a younger Stefan, just a little more depressing to be around and more full of angst. Although, to be fair to the boy, Jeremy had grown up a hell of a lot since Anna had died. There was less of the angst, less of the hatred towards anyone that looked at him the wrong way. Now, Jeremy wasn't a bad kid, which just meant that Damon felt worse about everything the boy went through. He still felt guilty over the neck snapping incident, and he was grateful as hell that the magic harry potter-esque ring had saved his ass. Then there was the time when he'd come home to find that Jeremy Gilbert had laced his alcohol with vervain and was sat holding a home-made stake, looking as if all the world rested on his shoulders. He'd gone on about how his father had hated vampires, etc., etc., and how the kid felt he need to stand for something. The words running through Damon's mind were along the lines of 'they've screwed you up, kid', but instead he decided to patronise the youngest Gilbert. The kid did ruin his alcohol, so he was sort of entitled to it. But as the boy headed for the door, something in Damon made him call him back. He related to the kid, and then told him that 'in 1864, people knew how to whittle'. Jeremy insisted that it's harder than it looks, and Damon let it go with a 'huh' and a smirk.
And as for Elena… it didn't take an expert to know that he had feelings for her, and no matter how much he denied it, he cared more for her than he would've liked. He remembered when he and Stefan saved her from the originals the first time around, and as she came down the stairs, it looked for a moment like she was about to run into his arms. Of course, she ran straight to Stefan, only shooting him a glance from over her boyfriend's shoulder and mouthing a thank you. Damon had smiled and nodded, pretended to brush it off. He gave up hiding it hours later, when he confessed to Elena his love and made her forget immediately afterwards. He knew he didn't deserve her, but his little brother did; and that was why he couldn't be selfish with her. Damon drank himself to sleep that night.
Damon prided himself in not caring about anyone besides himself, although he sometimes allowed himself to make the occasional exception. Admittedly, he knew that for someone who possessed a devil-may-care attitude such as himself, he'd made several exceptions too many. There was little Damon wanted more than to be able to shut out his emotions again, turn his caring off like a light, but he couldn't anymore. Damon Salvatore cared, and it scared the Hell out of him.