Can you actually poison someone without applying the poison to your weapon? Like if someone is sleeping can you give it to them...erm, so to speak

Pickpocket has a perk allowing you to put poison onto someone's person, effectively poisoning them

Ooo cool, thanks I'll look into that

When you poison them that way NPCs don't react to poison. That is, if one poison doesn't kill them they will continue sitting on their chair and won't act as if they were under attack. You can keep adding poisons until they die.

If you put more than one poison of the same type in their pocket, only one will have effect.