Co-Worker Insists On Picking Up The Check

DEAR ABBY: I have a colleague who has become an amazing friend over the last few 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 for my meal. 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 — maybe a little selfishly — because it saved me money. But now I feel constantly indebted to her because I can never seem to return the favor.

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

Lately, I have come to resent the situation because I don’t want to 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 professional work relationship and the friendship we have built? Is this the altruism of a selfless person and my ego getting in the way? Or is there a deeper motive I haven’t considered? — TREATED TOO WELL

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

DEAR ABBY: My niece’s mother-in-law of 32 years, “Helen,” died seven months ago. I have been quietly seeing her widowed husband, “Wayne,” for about three months now. We knew each other only socially up until then. After Helen’s death, my niece, her husband and their children went on vacation because Helen’s illness had been a long, drawn-out 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, as they say, the rest is history.

The problem is telling his children and grandchildren. He and Helen were married 59 years but didn’t have a happy marriage for the last 23. Should we tell them or continue keeping 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 for another few months — until it has been a year since Helen’s passing. At that point, Wayne should tell the niece and other 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.

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