BORROWING or lending money to a friend can lead to problems.

Dear Marilyn,

About a year ago I lent a large sum of money to a close friend. He still has not paid me back.

He has been my best friend since fourth grade. I am in college now, and we are actually more like brothers than friends. At the same time, a thousand dollars is a lot of money. I believe that “business is business,” and the fact that we are friends should not prevent him from paying me back what he owes me.

   He has said to me that if I was really a friend that I would not ask for the money back, since I know that he does not have any extra money to pay me with. Should I learn to forgive and forget in order that my friendship with him will continue? Or, should I risk losing a friend and take legal action?

I am pretty upset. Please, Marilyn, what do you think that I should do?

Signed, Irritated Friend

Dear Irritated Friend,

   You are in a tough spot. If you had asked for my advice before you had lent the money to your friend, I would have absolutely advised against it.

   This is because what has happened to you, unfortunately, was rather predictable. A person should never lend money to a friend, because many times you lose either the money or the friendship.  Since you have already done it, you may ultimately have to choose between these two options yourself.

   The first thing to understand is that your friend is very wrong to tell you that a true friend would not ask for the money back. The opposite is true. A true friend would PAY the money back to the friend that was nice enough to loan it to him in the first place.

   The second thing to think about is that there is no way that he is going to pay you back without a plan that works for both of you. Even if he did come up with an extra thousand dollars, it is highly unlikely that he would pay you back with it.

   So, talk to him. Tell him how much his friendship means to you, and that this situation is putting a real strain on your friendship. Determine together if there is a sum of money that he could pay you each month, to work down the debt.

   If you do agree on a sum, and he pays it, great. However, if he does not pay it, then you have to decide what you will do at that point. You may truly have to choose between the money and his friendship. I can’t make that decision for you.

   Either way, learn from this. Don’t make this mistake again with anyone. The price of this lesson was high.

Dear Marilyn,

I have a really close friend that I have known for six years. She recently started to go out with a guy, and he is her first real boyfriend.

They spend every hour of the day together. Now that she has a boyfriend, she doesn’t even call me. The only time she does spend with me is when he is working, and she wants someone to hang out with.

I really do not like this guy. He is very controlling. He always wants to know what it is that she is doing, and who she is doing it with. I do not think that she is in a healthy relationship. Do you think that I should I tell her how I feel about this guy? I don’t want to risk losing our friendship.

At the same time, I don’t want her to get hurt. I have a feeling that is exactly what is going to happen. What do you think that I should do?

Signed, Best Friend

Dear Best Friend,

   When it comes to matters of the heart with your friends, the best thing to do is to say nothing. If you point out his shortcomings, she will defend him. If you tell her that you are afraid that she will get hurt, she will say that she really doesn’t think that she will.

   The truth is, of course, that even if she realizes that what you say is true, she will be hoping that everything will turn out right. So, just be there for her, and be a good friend to her. Let the relationship run its course, with no input from you.

    There is a good chance that she will be a friend to you a lot longer than she will have this guy as her boyfriend. Be patient.

Dear Readers, please send your questions orangecountytribune@gmail.com. Put “Dear Marilyn” in the subject line.