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Contrary to popular belief, Nightmare could in fact feel positive emotions, and emotions that weren't negative. He didn't like it, but he did nonetheless.
Sometimes he would think back to when he was trapped in the tree, it was definitely a lot easier back then. All he had were his negative emotions and even when he took over his current body, he believed that he was pure, concentrated negativity.
Unfortunately, fate had another idea, because the body he inhabited was defective, broken before he even got a chance to take over. Hence the goop covering one of his eyes.
Even he didn't quite understand it, but it seemed that due to this flaw, a piece of the previous Nightmare still stuck around. Not necessarily alive, but sometimes Nightmare could feel his presence lingering.
Additionally, this defect allowed him to feel emotions other than utter hatred for everyone around him. Of course they were dulled by a lot, but the burning sensation he felt whenever he saw something slightly amusing told him that they were in fact there.
He hated it, hated being able to feel positive in any capacity, hated having to control his emotions when previously he only felt anger.
What he hated most of all however, was that he began caring about his idiot subordinates.
It was so simple at the start, when he had just gotten Killer on his side, forever loyal to him. He did a lot of messed up things to get him, and back then he didn't feel guilty at all.
That's because that was who he was, pure negativity, why should he care about a servant?
But now... now when he looks at Killer, there's a strange feeling in his gut, guilt. Not that he'd let anyone know, ever.
Once he recruited Dust and Horror, he was able to avoid Killer, avoid the monster that he had created. He wasn't as cruel towards them, harsh but not to a cruel extent.
He often wonders why he changed, why he's helping Horror give supplies to his AU when previously, he would have just broken him down till he had no choice but to join him.
Why he lets Dust waste his off days away being lazy, when previously, he would have forced him to train, pushed him to his most extremes without batting an eye, just soaking up his misery.
It gets worse when he meets Cross.
Cross, who was trapped in the void of his AU, visited only by Ink. In some ways, Nightmare empathised with Cross. The previous Nightmare and Cross both ended up the way they were in similar ways.
Attacked by everyone and in return, killing them all.
Cross was vulnerable, easy prey. He was so desperate to bring his AU back that he took up Nightmare's offer without much thinking. Of course, it didn't take long to wear Cross down, whispering doubtful words to him on the regular.
They'll never forgive you
But even then, he couldn't help but be nice sometimes. Like giving Cross an option of joining his gang. Typically he'd have broken Cross down by this point and Cross would join naturally.
He tried telling himself that it was because Cross needed a more gentle approach, due to his distrust towards others. He told himself that this was the most logical way of convincing Cross to join him.
And you may be wondering, why did Nightmare need so many subordinates?
Well, even he doesn't know.
Killer would have been just fine, Dust and Horror good additions, but not essential, and Cross seemed like too much effort.
Some may say that it's too match up to Dream and Ink, who were both practically immortal gods, but even that wasn't quite right.
Nightmare didn't like to think about it, as it would have him face realities he didn't want to accept.
The reality that he had begun to care. He had begun to care about these broken monsters, abandoned by everyone and left to suffer.
So he doesn't accept it, he lashes out and hurts those around him. He sees the way Dust stays in his room more often, the way Horror doesn't stay in the castle at all unless he has to. The way Cross' adoration soon turns to neutrality.
The way Killer stops striking up conversations with him.
Killer, despite everything Nightmare had done to him, was unflinchingly loyal to him. And he was always bright and peppy, despite having no reason to be.
Inside he was full of negative emotions, but it didn't make Nightmare as happy as it used to be. Now, Nightmare felt like he wanted to... help him.
He hated feeling this way, and the next time Killer tried talking to him...
Long story short, Cross and Dust had to step in to help Killer get through a panic attack and prevent Nightmare from hurting him even more. He stopped trying to talk to him after that.
Nightmare should be happy, no more Killer yapping around means he doesn't have to confront any guilt he may or may not have developed after getting close to the guy.
But the atmosphere is strangely silent without him around.
Even so, Nightmare refused to acknowledge his growing fondess for his boys. The way they bicker with each other, but are so obviously fond of each other. Even Cross, who had only joined a few months ago seemed to fit right in.
Sometimes he asks himself why he doesn't allow himself to be a part of it. Then he remembers what he did to Killer, and steps away.
It reaches a point where he can't deny it anymore. He really cares for this group that he's created. He loves each one of them yet he can't even express it without causing himself pain.
No matter what he tries, he ends up hurting them even more, so he stops.
He knows, he knows that they believe that he hates them, that he's only using them. He wishes that were true.
In a simpler world, he wouldn't care for them at all, and wouldn't need to feel any of these confusing emotions.
But in this world he does, he feels so much and it hurts, but he wants to make things better, he really does.
He wants the gang to be able to smile and joke around in his presence, he wants to be able to tell them that he appreciates them without wimping out in the end.
One day, he goes to Outertale to clear his head. Who else does he meet but Error.
As shocking as it may be, he let everything out to Error, who acted like he couldn't care less but was obviously interested in the drama of his life.
"And sometimes when Cross gets mad, he'll start cursing in Spanish," Nightmare chuckled, but this bit of information seemed to really get to the glitch.
"Well t-then! What the h-hell are you waiting for?!" Error proceeded to encourage him to make things right with the gang, and oddly enough, tells him that Cross was welcomed in the Anti-void before running off, mumbling something about an 'Undernovela'.
Despite the strange way he went about it, his words really stuck with Nightmare. He wanted his gang to feel at home in his castle, he didn't want them to fear and submit to him anymore. He'll do better and treat them better from now on.
That's what he wants to do, anyways.
It's easier said than done, the words getting caught in his throat and the awkward silences aside, he doesn't really know what to say.
The next time he tries to talk to Cross, he ends up just sending him on some mission before even really getting to say anything important.
He sighed, massaging his temple as he thought about what he'd do next.
Ok, no backing out now, when Cross comes back, I'll gather all of them and express my gratitude all at once!
(Then Cross disappeared.)