A good friend has alienated me and several other close friends due to her compulsion to tell us how much she spends on things. She's quite wealthy but seems to have forgotten that not everyone has her kind of money to spend on luxury items. Should I talk to her about it? Or is this an issue of insecurity I need to keep working on within myself? [more inside]
I pissed off/offended one of my oldest friends recently and I'm at a loss as to how I should proceed. I asked her for a favor I've never really asked of any of my friends before: if she had the means to loan me around $200, though I made it clear that a lesser amount would help just as much right now. I told her I'd be able to repay it in approximately six weeks. She didn't take any of this well. [more inside]
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?