DEAR ABBY: Man wishes good friendship was something more

An advice-seeker is hesitant to reveal to his younger female pal that he is interested in a romantic relationship.

Published May 07, 2026  •  Last updated 24 minutes ago  •  2 minute read

Portrait of a happy mature man smiling with young woman Photo by m-imagephotography /Getty Images

DEAR ABBY: I’m a 60-year-old man. I have a close female friend who is 20 years younger. We see each other just about every day and call each other to talk about our day. We have supper together just about every night. The only thing we don’t have is a romance. I have strong feelings for her and want to tell her how I feel, but I’m worried that if I do, it will ruin our friendship. Do you have any advice for me? — CLUELESS IN ALABAMA

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DEAR CLUELESS: What’s going on is unsatisfying for you. This younger woman knows you care about her and have much in common. She may not be aware that you have more in mind. If you don’t speak up, your relationship with her stands no chance of moving to a higher level. If you do, and she tells you the chemistry isn’t mutual, you will then be free to find a woman who reciprocates.

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DEAR ABBY: I recently retired after a 25-year career in law enforcement. My mother, whom my family and I see a lot of and have gone on vacation with in the past, didn’t get me a congratulatory card. I was hurt by it because she’s usually more thoughtful than that.

Mom also lectured me about going on vacation after my retirement, saying it was selfish. I had planned to go with my wife and daughters, but they couldn’t go. I ended up feeling guilty and stayed somewhere close for two days.

What are your thoughts on this? I try not to let it bother me, but it was hurtful. — NEXT CHAPTER IN NEW JERSEY

DEAR NEXT CHAPTER: I see nothing selfish about taking some time for yourself after your retirement. You were certainly entitled to it. It’s unfortunate that the timing didn’t work for your wife and daughters. Is it possible that your mother was upset that you didn’t invite her, or might be jealous that you have been able to retire?

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DEAR ABBY: I work with a woman who is frequently paralyzed by the possibility that she might do something incorrectly. When writing reports or sending emails, she checks her work again and again, asking multiple people to confirm that she’s taking the right approach before proceeding. This is much too slow. It annoys the people she’s badgering.

How can I help her relax and understand that there are no negative consequences for being wrong occasionally? We’re not brain surgeons. If we make a mistake, it’s likely someone will catch it before it comes close to causing a serious problem. Reassuring her that she can be bold only seems to cause more terror. Please help. — LOSING PATIENCE

DEAR LOSING PATIENCE: It’s time to stop coddling your co-worker. The way to show her that mistakes are OK is to let her make mistakes. Praise her after she has done something right, and gently correct her occasional blunder. She may be uncomfortable for a while, but everyone will be happier in the end.

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 DearAbby.com or P.O. Box 69440, Los Angeles, CA 90069.

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