Every time in my adult life that someone asked to borrow petty cash, I have cringed inwardly. I hate to owe and hate it more to remember that I am owed - I'd much rather give it away and spare myself the needless agony.
Until oblivion takes over, I cannot help thinking "He/she still owes me the money they borrowed a month ago" every time we meet. It gets harder to remind them about the "loan" as time passes until it is actually impossible - typically the two month mark is when I know to call it a "bad debt".
My indecent haste to return any money I've had to borrow is viewed to be in poor taste by the "loaners". They most likely feel insulted.
An application that takes the sting out of social borrowing, lending and sharing of money and bills has been long overdue. I am not sure if BillMonk is for me - but it surely has the woes of people like me in mind.