In 1.07 Bachelor Party, Angel does not realize Richard is a demon until he sees him change at the restaurant. However, Angel can smell the difference between humans and demons. From City Of:
Doyle: “I like the place. I mean it’s not much with the view, but it has a nice bat-cave sort of an air to it.”
Angel: “Who are you?”
Doyle: “Doyle.”
Angel: “You don’t smell human.”
Doyle: “Now that’s a bit rude. So happens that I am very much human…. On my mother’s side.”
Therefore, he should have known upon meeting him at the office.
Related episodes: 1.07 Bachelor Party
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