I've lost a lot of "friends" the same way. I long ago learned that any time you loan someone money be fully prepared to never see it again. The best people though, imo, are the ones who as soon as they realize they can't pay you back when they thought say so and offer to make it up to you another way. As someone who often has to back out of a commitment due to my fluctuating and unpredictable health problems I care less about keeping the promise and more about if they make an effort to make it right when they can't keep the promise. I also don't loan anyone money anymore though. It's not worth the headache.