I'm wondering how someone can email you money?

At any rate, it sounds like, as the chance of you and her resuming a friendship goes down, your interest in getting repaid the money goes up. I guess that's only human. When you loan money to someone, there's always a chance of not getting all of it back. Even when that seems to be happening, I don't think it's all that cool to be telling others that she owes you money. That should be between you and her. If she is aware that you've told someone about the loan, that could make her feel bad.

You seem to go back and forth between having fond feelings toward this young woman and taking a pretty harsh view of her. It's like you think she's either a very dear person, or she's a douche. That's pretty extreme thinking. She might be somewhere in between. Most people are.

This gal has an 18 y.o. daughter. So she's into her 30s, maybe pushing 40, or beyond. The relationship she had with her daughter's dad fell apart. So she has just her own income to depend on. She's surviving on what she makes waitressing. It wasn't enough to allow her to keep her house. The loss of the home meant the loss of a lot of dreams. She wonders if she'll have money for her daughter's wedding, which may come up in a few years. She's sad that future grandchildren will be visiting her in an apartment, instead of playing in her home with a yard. She's wondering what she'll do when she's 60 years old. It can be hard to waitress at that age, and she can't get full Social Security until she's at least 67 or older. She may not have money saved in a pension plan, and that worries her. Maybe her life was going to be way different, if she was in a marriage that was working out. That dream fell apart. This person has worries . . . major worries.

You may not be a lot younger than her, but you are at a whole different phase of life . . . because you don't have to worry about any dependents. She sees time running out for her. She's not where she thought she was going to be at this point.

Like you, I have no kids. I skip through life footloose and fancy-free. I see how women with kids look at life drastically different from how I do. When a woman, with even just one child, loses a partner, life becomes tough . . . especially if that woman is not in some high-paying profession. There is much about this gal's world - and the challenges in it - that is outside the scope of your experience. That can make forming a bond hard.

It's not that you're a failure as a human being. It's more that she is recovering from failures in her life - which she will probably never fully recover from. And how much of this even occurs to you to think about? You do care about people's problems, when you know what they are. There's a lot you don't know.