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Handing her money in public embarrasses her. This older man needs to be tactful when he hands her money in private. A gift of money should be in private.

By Tom P Blake - Finding Love after 50

One day, when I owned Tutor and Spunky’s, my Dana Point deli, I noticed a man and a woman seated in the dining room but thought little of it, other than I noticed that the man was eating an entire quart of chili on his own.


Ten minutes later, the woman poked her head into my office. She said, "I'm Angie. I know you write that dating column and wanted to ask you a question." The man she'd been with had already left the deli and was waiting for her in his large white pickup truck in the parking lot.


Angie said, "That man I was having lunch with is 22-years-older than I (she looked to be about 50). Out of kindness, he likes to give me money, which I appreciate. He expects nothing in return. He knows times are a little tough for me these days.


"But, he hands it over to me in public and people notice. It makes me feel cheap. Like, just now, in your deli, he handed me money and other customers saw him. They looked at me and I could guess what was going through their minds. Or, perhaps they thought he is my dad. Believe me, the money is not for any services rendered.


"How do I tell him that when he hands me money in public, it makes me feel cheap--without hurting his feelings?"


In 23 years of writing columns, I have never had that question asked of me.


I had to answer right away because she had to get to the pickup truck.  


I said, "There's no way around this except to be direct and honest. Tell him first how much you appreciate his gesture, and how helpful it is to you during difficult financial times. The, tell him exactly what you just told me in the same kind and thoughtful way, and reassure him again how much you appreciate his gesture. Be sure you couch your comments in a very warm and friendly manner.


“My guess is he is completely oblivious that he is causing you embarrassment. And, he likely cares a great deal about you to be helping you by giving you money.”


She shook my hand, thanked me, and ran off. "I'll let you know how it turns out.” Then she winked and added, “I care for him a lot.” She headed toward his truck.


As they drove away, I thought, I hope my advice to her won't cause him to stop giving her money. Perhaps I should have told her to not worry about what other people think. But, as I re-ponder her question, I still think my first answer was the correct one.


This isn’t a financial issue as much as it is a communication issue. The couple just needs to talk about it to be sure they understand each other. She has a lot of pride and he needs to respect that.

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