Friend 1 (overdraft blood) I've known since I was 17. That's 31 years ago.

I've loaned him money in the past and helped him out before - and with the exception of a streak of bad luck AND bad decision in the last 6 months he's always paid me back - and helped me when I needed help like moving furniture, or feeding my cat or helping my mom, other things.

Friend 2 I've know since 1990 - so 28 years.
Same exact deal as friend 1 - just met after high school. Always paid me back. Always helped when I asked - but slight less than friend 1. but less demanding/annoying than friend 1 on a friendship level. Way more mellow.



So it's just now that we're all nearing 50 that my life is going well and their's are falling apart. They've been falling apart slowing for years - while over the last 12 years my life has become much better/easier. I outright own my condo. I've had a job for the last 12 years and it pays well. They have no savings and are living hand to mouth.

But I've also been getting more anxiety as I get older - I plan more and I'm less willing to take risks with money.