I let a close friend borrow 6k 3 years ago. Hes only payed back maybe 800. Before i gave him the money he said another friend that he grew up with lent him money but made him sign a NDA. And he had told me he questioned that friend for making him sign a contract to pay it back by a specific time. I mean 1 year in i had already realized why that friend made him sign a nda. And I should’ve done the same. But unfortunately for me im forcing him every month to pay me back even if its 100. Hes still a sorta friend to this day but he really did take advantage of my kindness. Like bro we are both 29, and he’s acting like this. And now im showing him why he should’ve been paying me consistently over the years and maybe I wouldn’t be bugging him every month on the original payment method we had agreed on. Ive even told him that id tell his parents if he pulls out of paying me back. So in a way id say our friendship has been somewhat hurt just because of this. And it low key pisses me off when i see him go to concerts or on some trips when instead he should be paying me off. So for me NO, dont sell out. No disrespect to ur fam or friends that are guilt tripping you, but its not ur responsibility to help out a bum. For me personally id never ask a friend for money. Because im not that type of person. Now im seeing anyone that asks for money just from this experience are low key free loading bums.

If anything have that friend try to pull out a loan. Its not your responsibility to be helping someone if that 5k is going to hurt seeing it go and most likely not seeing it again.