I can't be bothered to write a ton again half the chapter isn't loading for me either way.
It's difficult to tell if Cirrus is blatantly messing with Skylar about giving the photos back. Even if he did, he could still tell Chan-il about them.
I'm sure his view on Skylar is gradually changing, based on his reaction to Skylar's dreary expression in the yearbook. Like Cirrus' said, he does look like he can't speak up.
Whether Cirrus feels sympathetic or not, it's not easy to tell immediately. It's not like he's completely emotionless, but considering previous chapters it's hard to know specifically when it comes to Skylar. Really poorly analysed, I'm sorry. 😓
I forgot to add this in the last chapter, but when Cirrus brought up he would be a more interesting subject, it feels like he isn't actually fond of Chan-il. Or, his ego is high. In general, it feels like he doesn't feel anything for Chan-il at all.
Cirrus' behavior might correlate to his home life, considering how his step-mother is treating Candy and him. As she threw the heel toward Cirrus, you can see a similar expression he made about Skylar in the beginning, where he called him an idiot at the end. Except he comes off as genuinely upset this time, instead of finding Skylar's relief and apology extremely stupid after masking how he felt when Skylar did break down.
His family, one way or the other definitely has contribution toward how he acts and behaves. Abusive homes can create behavior like this from my own experience. Though, it's not like his reaction was unreasonable. I've reacted the same way and said similar things when I dealt with the same thing. There could be many other factors that add up to why he's like this, but I've forgot half the manhwa since then and it'd just be spoilers.
Is Cirrus actually sorry? I'm taking him as more apathetic
It's moreso he's just using Skylar for entertainment, considering maybe a chapter or two back he said "I found myself a new toy, thanks to Chan-il." Which was one way or another, referring to Skylar.
At the end, he said Skylar was making it interesting for him and that he had nothing against him. So, really, he doesn't genuinely care much about the fact Skylar took photos of Chan-il then, right? And that he's just using him for pure entertainment because of it, not that he cares about it.
Earlier in the chapter, he came off as upset and mad, but I feel like he knew Skylar was going to come running at him once Chan-il was gone. It's either he's playing dumb or genuinely got irritated over Skylar's reaction. But playing dumb seems more reasonable considering way back in the beginning chapters, he called Skylar an idiot. He did say he'd keep the secret from Chan-il, which he's kept until now, not that he wasn't going to toy with him.
From my perspective, I feel like Cirrus is finding a way to make things more awkward between Skylar and Chan-il, in other words trying to change his view on him.