Never lend money to someone unless you're fine with not getting it back.
An individual may ask to borrow from you when they have exhausted all other options or can't get the money elsewhere.
Money can negatively affect your relationship. Avoid lending money in the first place, and if you do, never give more than you can afford to lose.
Lend them money with the assumption that it is a gift and you will never get it back. This way you're less likely to feel hurt.
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