I think it depends on how much money one of my possession is worth. and If the item has sentimental value to me. If one of my possessions cost under $20, and I don't have much sentimental value with my possession, I may let the person look after my possession or borrow it for an extended amount of time.
I won't lend my favorite pen to someone I just met even if my item is only worth a few dollars because it has sentimental value.