Oh my lord, I have been in this situation more times than I care to think about. And it always involves the same person. My problem is that I don't know how to say no....especially when I know the person really needs it. The amounts of money borrowed kept getting bigger and bigger and the time it took to pay back always got longer and longer with more and more excuses.
My husband and I finally said to each other, if we don't have it to "spare" then we need to just tell them we don't have it. We ran into problems because we would loan them money that we had set aside for our own expenses with the promise they would pay it back within a week or two. Something ALWAYS happened that they NEVER paid the money back when they were supposed to and it caused us to get behind in bills, we even had to get food from a food bank because we lent them our grocery money.
It almost ruined our relationship with these other people because we felt taken advantage of.
If you loan someone money make sure it's not money you need to get back and if they pay it back they do and if they don't, they don't. Either that or don't loan it in the first place (if you're like me that's where you get stuck lol)