UngeheuerLich
Legend
If a seemingly harmless person is always assumed to be a threat, be sure to always bring one with you. So you are never surprised.
It does not matter which person is noted. If you notice ANY threat, there is no surprise at all.
Or is it schroedinger's surprise: if the seemingly harmless person draws a dagger then you are not surpised anymore, even if you went before him?
So better use the deception vs. insight variant or stealth vs. perception to draw a hidden dagger. Otherwise you run into logical problems.
Maybe if you tell the DM you are suspicious of the person you are speaking to you may have advantage if there may be a good reason or you can make a perception check to notice hidden weapons even before they are drawn.
Other
It does not matter which person is noted. If you notice ANY threat, there is no surprise at all.
Or is it schroedinger's surprise: if the seemingly harmless person draws a dagger then you are not surpised anymore, even if you went before him?
So better use the deception vs. insight variant or stealth vs. perception to draw a hidden dagger. Otherwise you run into logical problems.
Maybe if you tell the DM you are suspicious of the person you are speaking to you may have advantage if there may be a good reason or you can make a perception check to notice hidden weapons even before they are drawn.
Other