I won a lot of money from my neighbor. He keeps promising to return it to me but I doubt it will ever happen. I am afraid he will stop inviting me to play because it upsets him that he owes me money
It's tricky to talk to someone about money, especially if your relationship is not strictly business. Some ideas you can use:
Use humor. "Can you at least pay for my funeral service after I die?" Humor removes defenses
Show them that your need for money is real and outside of your control. For example somebody is expecting money from you.
Give them an opportunity to come up with a solution. Tell them that you are willing to work with them on how to make this happen, ask them what do they think is the best way for them to come up with the money without making it too stressful for them.
Let it go. If your friendship is more important, consider forgetting about it. In this case make sure the other person doesn't feel like they own you anything, because it will be always on their mind when they see you.
Sometimes we are in a situation when we need to stand up for something or someone. Is it worth risking our relationships, or safety or our image for saying the right thing? How do we say it so that the other person actually takes it in, instead of creating a conflict?
Understand yourself. The reason you feel like you need to confront is because your needs are not being met and it makes you feel certain way. For example, the need for fairness is not met and it makes you feel angry.
If somebody is hurt as a result of the offender's communication or action, understand what the victim must feel and what needs are not met for them.
Find the right moment and talk to that person one on one, trying to be friendly and having an intention for the other person to understand. This is much more effective than having an intention of being right or trying to punish somebody
Ask what the person got out of this conversation, if they actually understood.
It is easier said than done, considering we may get emotional when communicating. Well, the easy way is never to have this conversation, but we don't want easy, do we?