Orders under duress not being enforceable. That's surprisingly legit for an Evil organisation.
So he wants a demon lord to ally with, intimately, not to fight.
Him feeling guilty about something is rare.
Being a knight doesn't necessarily means you follow a moral code of ethics. It means you follow a lord, though.
"I'd never do something so stupid."
Not a lot of believability there.
Ordering the most expensive thing is a good way to make sure he doesn't offer again.
Grimm might be mostly useless, but she's cute, so it's fine.
She said it! She said the thing! She said "kuh, kill me!"
But no orc in sight, so she only gets half credit.