I can't decide if I should offer any financial assistance to an old HS friend and his family who are facing some heavy duty medical bills also while enduring extended unemployment. [more inside]
How to politely bring up money to a friend before I work for free? [more inside]
How to help recover $400+ owed to my mother; or how to help her let go of this (minor) debt and move on? [more inside]
A friend of mine is coming in from a couple hours away (each way) for the night (halloween party), and money is tight on her end. I would go pick her up myself, but have to work late into the afternoon and wouldn't have time to drive up and back twice between today and tomorrow. I want to give her the money for gas (I am in a much better position financially), since I know this is a big expense for her and she is saving me the trip, but she is very independent and does not want me reimbursing her. How can I get her to accept it without making damaging her ego or seeming like this is out of pity?