If you ask Angel Dust, Charlie overthinks things.
Cornily convoluted plans for redemption, step-by-steps dependent on the success of the step before. She'll brainstorm up a hundred different rainbow tangents, all in response to what could be the tiniest little non-issue.
He doesn't mean to pass judgement on the Princess cruelly. Granted, he's made his personality barbed and sharp on purpose, everything that comes out of his mouth tends to be on the obnoxious side. Plus, when he's in the middle of a comedown, he can't exactly cope with a bombardment of enthusiasm, or platitudes from someone who's obviously never been in his high-heeled shoes.
Angel remembers overthinking things too, though.
Trying to meet his father's expectations. Juggling secrets; two contrasting lives. Struggling to puzzle out his once-and-neva' future with fewer & fewer pieces every day.
(What Val did (does) when he questioned or talked back or scrutinized the soul contract or just tried to make his own choices…
No. Don't think about it.)
Point is, overthinking never took takes Angel Dust anyplace good. The euphoric oblivion of being doped out of his mind is hugely preferable.
But Charlie consistently asks Angel how he is each day, and keeps on inviting him to take part in group activities (especially as the Extermination looms), and after this long the spider has let himself be convinced it's because she cares.
He remembers overthinking because he cared cares.
Deep down, he hopes the Princess doesn't burn herself out with it.
A/N:
I notice I keep writing angsty Angel Dust chapters without meaning to… (I'm sorry)
One thing I really would like to see at some point in the Hazbin series is Angel confronting Charlie over whether she actually understands or cares - I think it's a necessary thing to address. I don't doubt Charlie's good intentions, but it does come across in the pilot that she (& to a greater extent Vaggie) are more concerned about the Hotel's reputation than Angel's well-being, coupled with her fairly simplistic understanding of sin & redemption.
My interpretation of Angel is that he has great capacity for empathy, despite all the personal shit he's got going on, and that he'd be able to recognize Charlie's genuine good intentions at some point. Self-doubt, pressure & shit from Valentino, and that Angel puts on an edgy persona to protect himself/others would probably be the main obstacles to confront.