I know there are people out there who have loaned friends money before. My main question is do you regret it or not and if so why?

Long story short; I am doing fairly well for myself, 32 have large savings and am paying off a mortgage on my own house. That being said I have loaned friends money to stay out of debt many times, as I already went down the road and it is hard to rebound. 90% of the time they make it up but there always are the cases where they just can’t.

Most recent situations:

My best friend’s kitten had broken its leg and I covered the medical bill as my friend had no way to pay it.

I noticed my friend struggling to survive the month so I decided to halve his payment and asked him to set a budget for his pot use.

An old friend will generally come to me if she ever needs help and 9 times out of 10 she repays any loan. However her classes interfered with her work schedule and she is in the process of looking for a new job, so I won’t see the money anytime soon. I told her to just focus on school as the loan I gave her was for her books.

Just want to clarify, in my situations I always can part with the money I loan out. I don’t give my friends a timeline or anything to pay me back, I just say here is the $$ pay me back whenever you can if you don’t I won’t be helping you next time. The thing I’m trying to find out is if people have good/bad stories about loaning money to a friend.

Moral of the story, When you loan money out don’t expect it to ever come back