It's good you are taking it slow.

I have a tendency to "believe" what people tell me until they start telling me so much that it begins to not add up.

There was someone at work who sat next to me in a call center who's sob story (single mom saying father did not pay child support/car broke down and didn't have the funds to fix) motivated me to give her cash. I only gave a small amount ($40). I never lend money to people. I either give them a gift that I can afford or nothing at all. When she started coming up with other sob stories about needing money; that was when I began to believe it might be a lie plus I later overheard her talking about going to "B@@@@ ******" (a place where you can play poker) and thought--what kind of single mother low on funds goes and plays poker on the weekend? At that point, I figured I had been had but that is why I didn't give too much in the first place or expect the money back.. That she was the kind of person who would take advantage of other people made her a not so nice person and I felt sorry for her child!

Though I believe in listening to your gut--some people have become so good at "playing" others that you can still get had. Try not to worry about being cold and distant--guilt is a tactic that users use!