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Dear Abby: Senior woman’s admirer lacks courage to confess

by Abigail Van Buren
in Entertainment
September 9, 2026
Reading Time: 3 mins read
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Abigail Van Buren

Abigail Van Buren

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DEAR ABBY: I’m in love with an older woman. I’m 41, and she is about 35 years older. I have known her since I was a kid. She’s the reason I always dated older women. I want to tell her how I feel, but I’m scared she’ll be shocked, and I wouldn’t want anyone else to find out my feelings, like her kids. I grew up with them. 

We always enjoy our conversations, and I often throw her little hints. When I do, she smiles and likes that I flirt with her, but I’ve never told her my real feelings. What should I do? — HIDING MY FEELINGS

DEAR HIDING: You have nothing to lose by telling her your real feelings. If you do, at the very least she will feel complimented. If there is a possibility that your feelings are reciprocated — well, you are both adults now. If her kids don’t object (once they get over the shock), you could have a happy life together. I say this with confidence because years ago a distant cousin of mine married a contemporary of one of her sons.

DEAR ABBY: What is the proper etiquette when dining out and a hair is found in your meal? I informed the server, and she apologized and gave me credit for a free drink. Others say they wouldn’t have eaten the meal and would have requested a new entree. What would you have done? — HAIRY SITUATION

DEAR SITUATION: A free drink is not adequate compensation for this unpleasant mistake. When you are presented with food that is inedible for any reason, the manager should be summoned immediately to comp the dish (or more), as well as to offer a sincere apology. When they offer to remake the food, you are within your rights to ask for a different entree. This should allay any suspicion that the kitchen staff might simply pluck out the hair and return the contaminated dish to you.

DEAR ABBY: I have a friend in her 80s who always needs to be the center of attention. When someone is talking, not only does she interrupt the speaker, but she also distracts the ones trying to listen by dragging out pictures of her grandchildren. 

She often makes inappropriate sexual comments. She even brought up the subject of sex with my husband! People don’t want to be around her. However, she will give the shirt off her back and go out of her way to help anyone. How can I tell her that her conversational style is off-putting without hurting her feelings? — SUFFERING IN SILENCE

DEAR SUFFERING: This woman has several bad habits, so don’t expect her to correct them all at once. Privately and gently tell her you are not comfortable with her racy comments, nor is your husband. If she begins to show more restraint, be sure to express your sincere appreciation so she feels good about the effort she has made.

If her bad behavior is a sudden change, it may be a sign of a medical issue. Tell her you have noticed that she hasn’t seemed like herself recently and ask if she is keeping up with her medical exams. If you are acquainted with her family, urge them to have her evaluated by her doctor.

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Abigail Van Buren

Tags: Dear Abby

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Published on September 9, 2026 and Last Updated on September 9, 2026 by DC