Dear Amy >> I am friends with a single mother who works two low-wage jobs.

There are some months when she can’t pay her bills.

I have loaned her money many times.

The problem is that it’s like pulling teeth to get my money back.

She seems to feel that since I get a decent retirement check and Social Security check, I don’t need my money back.

Also, whenever we go out to eat, she feels like I should always pick up the tab.

I worked for 33 years for the state where I live, which has one of the highest costs of living in the entire country, so I need to be careful with my money.

How can I get her to understand that I need my money?

— Generous

Dear Generous >> One way that people successfully get loans repaid is to make it clear that no more money will be loaned until the previous owed amount is repaid.

However, I think that your expectations of this hard-working single mom are unreasonable. She is barely keeping her head above water, and in helping her you are also helping her children.

First, you should feel good about your own generosity.

Never lend more money than you can afford to lose, in case she can’t — or won’t — repay you.

And yes, you should pick up the check when you two eat out. Doing this is giving your friend a treat — and a break. If you can’t afford to do this, then you shouldn’t eat out.

Contact Amy Dickinson via email, askamy@amydickinson.com.