This has less to do with having money and more to do with understanding whether the person asking actually values you and your generosity regardless of their ability to pay.

It's unfortunate that some people seem incapable of feeling guilty. They have a victim mentality which only gets worse whenever people don't do anything nice for them.

If they're redeemable there is a point where you give them so much that they finally escape their problems and their attitude improves. Sadly this doesn't always happen and it doesn't always last.

Depends whether you're optimising for the bank balance or conscience.

Do you often consider friends and family as rich saps or marks?

No, for those people who would “ride for me” and vice versa I have loyalty and don’t mind helping them with money, but I’d expect to stay involved in their lives.

If they scuttle off, then they weren’t real at all, and I got played. I guess this supports OPs point, so I kinda get it.

However this group of people is not very large, most people I know aren’t getting money willy-nilly.

You shouldn't loan money to those people though, just give it without expectation of repayment.

Why not? I've borrowed thousands of dollars from family at times, lent thousands of dollars to them at others, and we've always repaid each other eventually.

It's normal to forgive a loan to family if circumstances change, or to give money no-strings-attached if they need it, but it's equally normal to loan money to help with cash flow problems and then expect repayment eventually.

>I've borrowed thousands of dollars from family at times

Is this common? Such a thing is unthinkable to me, and even friends from more businesslike families than mine have expressed major shame to me that they had to get a couple grand from their dad to cover closing costs (paid back within weeks)

Really? In my experience people pay back. When I was a student I and my friends ofent had to cover each other when buying tickets or whatever.

Yep, especially since leeches come asking for more and more.

And I understand if it's a sick kid or some other kind of an emergency... but people overstretch for luxuries.

This is certainly from my religious tradition and won't work for everyone but I consider it a blessing and a freedom that such discernment is not required of me:

> when you see on earth the man who has encountered the shipwreck of poverty, do not judge him, do not seek an account of his life, but free him from his misfortune. Why do you make trouble for youself? God has excused you from all officiousness and meddlesomeness. How much most of us would complain, if God had bidden us first to examine each person's life exactly, to interfere with his behavior and his deeds, and only then to give alms? But as it is we are freed from all this kind of annoyance. A judge is one thing, an almsgiver is another.

relationship dynamics change in many ways when you have disproportionate amounts of wealth

Its better to not focus on the amounts, as everyone has "fuck you money" at some level. I see it as something that scales based on your financial state.

Surely you've spent some amount of money on frivolity.

In my mind, "Fuck you money" is not just "money spent on frivolity"

"Fuck you money" is "I could afford to burn every professional and personal bridge that exists in my life and still be fine"

As in, you can afford to say "Fuck you" to the entire world if you wanted to.

> I’d rather be known as an asshole with backbone than a rich sap

This may be your particular disposition, but it is by no means universal. Given these two choices, I would much rather be known as a rich sap.

I think it’s important to note that a person can knowingly run the risk of being ripped off, not because they’re too stupid to know better, but because of their philosophical attitude toward money and how they relate with their fellow humans.

True, I guess my motivation is to break free of the crabs in the bucket that would bleed me of the success I’ve managed to acquire.

If one came from a different environment, material concerns might not be as pressing, and it might be a better strategy to placate said crabs in order to not lose one’s social standing.