well on the first one, i played it as good:
"My husband died and i need you to sell this for $500 so my family can eat"
"Sure"

Then played it on the dark side, which was pretty funny:
"My husband died and i need you to sell this for $500 so my family can eat"
"why don't i just take it from you and sell it for myself"
Not a waste of time, but a LOT of time.