"It's very hard to enjoy money when people you love are going through hardships that would be solved by an infusion of cash." True yes, but thats not sustainable and will continue to happen. You arent doing them any actual favors by enabling them to continue on with this same financially irresponsible behavior, you are simply doing it for your own guilt. "You give a poor man a fish and you feed him for a day. You teach him to fish and you give him an occupation that will feed him for a lifetime"