Should You Lend Friends/Family Money?

Lending friends or family money has been a very painful subject for me, and it caused relationships that once flourished, completely get demolished.
My expectations with lending the people I lended money were always high. I would always expect that they would honor their word, try to be as on top of things as possible (even though I was trying to be reassuring to them that I'd wait and I'd be flexible) and overall that their ethics and gratefulness would be through the roof, as they (presumambly should) want to keep a good friend around that's trying to help.
Boy, was I surprised. Nearly a decade later, multiple people have severely disappointed me. Partly it's my fault for being flexible, not setting clear boundaries, heck even giving the money out in the first place.
If you don't want to find yourself in the same shoes as myself, I'd strongly suggest to not become the "easy way out". 9-10/10 people will still figure out what to do if you don't give them the easy way out.
While I am sure it's very comfortable for these folks having a person that can solve their problems in an instant, that type of behavior usually leads them to more laziness, and the type of instant gratification that won't propel them forward to being productive individuals that will do what's tough to get problems solved.
When you lend money, especially without clear terms, you risk entering a grey area where personal and financial boundaries can blur, leading to potential misunderstanding and strain in relationships.
At the end of the day, when you lend money, you have certain expectations. The erosion of trust that occurs when these expectations are not met can have a profound impact on the relationship. Trust, once broken, can be incredibly hard to rebuild.
Acts of kindness are good, if you are trying to help someone out, it's great, go for it! But it's one thing trying to do someone a solid and loaning them money. Kevin O'Leary's approach is to outright deny the loan request but instead offer the money as a gift that doesn't need to be repaid. However, he makes it clear that this is a one-time gesture, telling them, "I don't want to lend you any money. I'm going to give you money and I never want it returned. But our contract between each other now is: you’re never going to ask again"
What do you think about this subject? Also, how has this impacted your interpersonal relationship when you did loan someone money?
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[@MichaelRosmer]

Great topic definitely agree rarely a good idea to lend money to family or friends

[@torontovoice1]

I couldn't agree with you more.

[@nikolatomov8874]

I find myself coming back to this quote by the great Kevin Kelly - "If you loan someone $20 and you never see them again because they are avoiding paying you back, that makes it worth $20."

[@JimPastirmatzis]

I get the point 100% but also most people don’t ask for $20.
Haha otherwise it’d be a relatively cheap mistake. Maybe we should be lending people $20 from the get-go as part of the trial process though 😂