Dear Rachel,

A while back, I loaned some money to an acquaintance who was in a really desperate situation. It was not a huge sum of money, but it was significant, and I was promised that I would be paid back. I didn't ask for it until I knew the situation was better, and then I emailed. I was told that the check would be sent in the mail. It never came. I emailed a few more times and then left a few phone messages. I never heard back. I am furious that I was taken advantage of and really would like my money back. I know Judaism teaches that you shouldn't bear a grudge, but don't I have the right to be angry?

Jerusalem, Israel

Dear S.C.,

There is no question that you are right that you are owed money. But there are times when being right and doing the right thing are not necessarily the same. We are taught that we should judge others the way we would like to be judged. When we judge with severity, according to the letter of the law, we are held to that standard as well.

I do not know this person or this person's situation, but let's give her the benefit of the doubt for a moment and try to think of what else could have happened. You write that she was in a really desperate situation. Can you be certain that the situation passed? That it was resolved? Perhaps it happened again? It is possible that this woman had very much wanted to pay you back, but then something else occurred and she was too embarrassed to tell you about it. Perhaps she kept hoping that she could mail that check, but time after time, she wasn't able to and was afraid you would be angry.

We can all think of times when we should have said or done something, but we didn't. As more and more time passed, we started rationalizing that too much time had passed and that it was too late to do what we had originally intended. I am not saying you have ever done something like this with money owed, but think about other things you did not handle properly, and that even years later you wish you had done differently.

You have assumed that this person has no intention of paying you back and is purposely ignoring you. You could be right. But again, it could be just the opposite. It could be that your loan has been eating away at this woman and she is filled with guilt about what she owes you and what you must be thinking about her.

We are now ending the month of Elul, the month preceding the start of the New Year. Elul is the month of rachamim, of empathy and mercy, and we are heading into Tishrei, the month of scales, of justice. But it is not justice we seek, but believing that there is Divine justice, and that ultimately, we will receive what is rightfully ours.

Think about how you would feel if the tables were turned. Be grateful for the fact that you are in a situation where you do not need to ask others for such help and you do not need to borrow money. Imagine what it must feel like to need to feel so desperate that you need to turn to mere acquaintances for help. And then think about how you would want someone to treat you if you were in her situation.

There is ultimately nothing you can really do to get your money back. You can continue to wait and hope that one day she returns it. You can continue to call and email and harass her hoping that she will give it to you (if she has it to give). I guess you could take legal action, but as you state, it wasn't a huge sum, so I doubt that is practical. Or you could do something completely counter-intuitive. You could do the incredible mitzvah of tzedakah.

As Jews, we are responsible for giving maaser, which is ten percent of all of our earnings, as tzedakah. Now tzedakah is translated as "charity," but in truth, its roots are in the word "justice." Why is the term "charity" misleading when it comes to maaser? Because charity implies that we are giving something to another that we don't need to be giving. However, when we give ten percent, the idea is that it is not our money to begin with. It is not ours to give. That is what we owe, that is what is just, which is why it is called tzedakah.

Furthermore, we are taught that if we want to be blessed with material wealth, the way to achieve that is to be generous in how we give to others. We are heading into Rosh Hashanah, and we all want a year filled with revealed blessings, physically, materially and spiritually. We also want to be judged with loving-kindness and to be forgiven for our mistakes. And it is a mitzvah, as Rosh Hashanah approaches, to we nullify all debts and promises.

It seems like it is no mere coincidence that you write this question at the most auspicious time of the year, when we have special directives to be generous and forgive debts. I would strongly consider looking at the tzedakah you gave this year and perhaps you will see that maybe you fell a little short. Maybe you will remember that you didn't give as much as you really should have. Or maybe you have, but giving a little more can only help! And if you do, then you have a tremendous opportunity to help this woman. You can email her one more time, and let her know that she doesn't need to worry about the money she owes you. You can tell her that you know things were tough in the past and she should consider it a gift.

Now, I realize this might seem out of left field as there is the possibility that she is fine, maybe even doing well, and you were really just taken advantage of. But that is her problem. Not yours. If this woman is doing something wrong, that is for her to deal with. You, however, are responsible for doing what is right, and sometimes even more than what is right!

I hope you are able to forgive this woman and her debt, and in doing so, you should be treated with the same loving-kindness. Ketiva v'chatima Tova! May you be inscribed and sealed for a good New Year!