Dear Abby: Sister in her 50s always needs money

DEAR ABBY: I have a hard time differentiating between enabling and just helping out my sister.

Throughout her adult life, even while she was married, she has never been able to make ends meet. She’s single now and in her 50s, a hardworking but underemployed, depressed individual.

I have a good job and I feel guilty if I don’t help her each month. (She doesn’t ask, but drops enough hints that I know things aren’t going well.) I have suggested repeatedly that she needs to find a better job. I even send her job leads, but I’m not sure she actually ever applies.

My friends and relatives say I should use tough love and stop helping her. But I hate to see her struggle, and I don’t want her kicked out of her apartment. I will be retiring soon and won’t be able to continue giving her money. What should I do? — SYMPATHETIC IN SAN DIEGO

DEAR SYMPATHETIC: Have a frank talk with your sister NOW. Ask her how many of the leads you gave her were followed up on.

Because you say she is chronically depressed, encourage her to see a doctor and find out what kind of help there is for her. It may be the reason for her divorce and for her inability to seek other work and improve her financial situation.

That you will no longer be able to continue assisting her financially is something your sister needs to know ASAP, so she won’t be cut off abruptly. This isn’t tough love; that you will be on a fixed income is a fact of life.

You have been a wonderful sister. You have done more than many people would, so do not feel guilty for taking care of yourself.

DEAR ABBY: It has been eight years since my first love, “Oliver,” and I broke up. It was amicable and we both had closure. I have been in my current relationship for six years. We love each other very much and have two beautiful kids together.

I don’t often think about Oliver and we haven’t spoken since our split. But the crazy thing is, I dream about him constantly. The dreams are pretty tame and they don’t make sense.

I don’t understand why this is happening. I know myself and I know I don’t miss Oliver. I’m happy in my current relationship. So what gives, Abby? — TROUBLED OUT WEST

DEAR TROUBLED: I’m sure it’s nothing to worry about. I was taught years ago that the things we see in our dreams are manifestations of our subconscious and are not meant to be taken literally.

What you are dreaming about may not actually be Oliver at all, but something he symbolizes. Perhaps it’s freedom, or youth — who knows? But if the dreams persist and they bother you, I’m sure a couple of sessions with a licensed mental health professional would ease your mind.

Dear Abby is written by Abigail Van Buren, also known as Jeanne Phillips, and was founded by her mother, Pauline Phillips. Contact Dear Abby at http://www.DearAbby.com or P.O. Box 69440, Los Angeles, CA 90069.

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