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dear abby OPINION | DEAR ABBY: Co-worker insists on picking up the check

by Abigail Van Buren | March 16, 2023 at 1:00 a.m.

Dear Abby: I have a colleague who has become an amazing friend over the years. We plan dinner dates or work conferences periodically, and we also try to book spa appointments together when we have vacation time.

“Sandy” is everything a person would want in a friend. However, when we go out to eat, she usually insists on paying. She has also prepaid some of my spa appointments. When this pattern first started, I was a little put off, but I appreciated her generosity because it saved me money. But now I feel constantly indebted to her because I can never return the favor.

When I insist on paying for myself, we argue. Sandy says she wants to show her appreciation for my partnership at work. She also explains that I have kids (who are expensive) whereas she is childless. She justifies it by rationalizing that her husband makes an impressive salary. They are comfortable, but not wealthy.

Lately, I have come to resent the situation because I feel like a charity case. Not only am I more than able to pay for myself, I also don’t want to feel limited when ordering food. Knowing she’s going to foot the bill makes me reluctant to order the food or beverage of my choosing.

How do I approach this without tarnishing our work relationship and our friendship? — Treated Too Well

Dear Treated: I am going to assume that you have already communicated to Sandy that this dynamic makes you uncomfortable. If you haven’t, do it now. She may be the soul of generosity, but some people use money to control others. Not knowing Sandy, I can’t guess what motivates her, but clearly the two of you should be able to have a conversation without anyone becoming defensive.

Dear Abby: My niece’s mother-in-law of 32 years, “Helen,” died seven months ago. I have been seeing her widowed husband, “Wayne,” for about three months now. After Helen’s death, my niece, her husband and their kids went on vacation because Helen’s illness had been a long ordeal. I was tasked with giving Wayne a nightly call to check on him, which I did. We realized we had a lot in common and the rest is history.

The problem is telling his kids and grandkids. He and Helen were married 59 years but weren’t happy for the last 23. Should we tell them or keep it a secret? — Unexpected Love In The East

Dear Unexpected: Although you have no reason to be sneaking around, in my opinion you should stay quiet until it has been a year since Helen’s passing. At that point, Wayne should tell the relatives that he thinks you have a lot in common and you are going to see each other. In a perfect world, everyone would be glad that the two of you are finding happiness after so much sadness.

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 P.O.Box 69440,Los Angeles,CA 90069 or visit


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