"he is not putting in the effort to do so, or is it me giving him the impression that I don’t need the money." You're right John, he is not showing appreciation for the fact that you helped him, or he'd at least make the effort, whether you look like you don't need it or not. Even a bank would expect you to re-negotiate a loan if you got it extended. Personally, I don't loan money anymore, ever. My philosophy is: "If I have it to loan, I have it to give, because I'd rather not risk a friendship over it." If I can't afford to let you have it, the answer is NO. I'm the kind of person that will get pissed about a commitment to pay back $1 if that's what it was - a commitment. On the other hand, I've given hundreds of dollars at a time, to help a friend or family member, with no strings at all (when I was in a different financial situation and could afford it without hardship to myself or my responsibilities). This is truly an excellent theme John. Nice job :-)