When you’ve had enough.
There is no perfect answer.
It all depends on how you are feeling.
If this is something you don’t want to continue, then it’s your responsibility to create a boundary.
The next time that person asks for money you could say “I can’t loan you money anymore. Every time I do, I never actually get my money back. When that happens I feel like I was taken advantage of.”
After you’ve said it stay strong.
Don’t let them get in your head and force you to make a poor decision.
Stick to it and eventually, they won’t come asking for money anymore.
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