Why do I let people off the hook all the time?

Amateur shrinks out there, I need help. What I mean is that I loan someone money or give them a break in some way and then when the time comes that really I should collect, I tell them oh, you need your money for your new house, your new car, your baby coming…whatever it is and then I don’t collect. Meanwhile I see them buying other things that promote them even further and I get a little ornery inside. These are always people close to me, not abstract situations. Diagnose me?