Like I know there's a tavern beneath Riften the first time I go there?
Quite immersive and RP friendly.
if you are such a role player you would have said no to bryn and started doing something else.
i ignored him, because my char is not a thieve. well after walking a bit around it was late, so i went to the tavern to rent me a room to sleep. there i saw the possibility to ask her about him...