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The tricky art of grandparenting

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By Bob Levey
Posted on April 09, 2026

The regular monthly meeting of the Grumpy Grandpa Group was called to order. We dispensed with the reading of the minutes and got straight to business.

Everybody healthy? Grunts, grimaces, nods.

Everybody rich? Snorts. Curses.

Everybody happy with the world situation? Glares. Eye rolls.

And everybody doing OK with family?

Up spoke one of our charter members, a guy who has always been sunnier than the sun itself.

His kids were always the greatest. His grandchildren were greater than great. Even the spoiled milk in his refrigerator was great.

But on this day, he wanted help.

He had been arguing with his son about Grandpa’s behavior around the three grandchildren.

Grandpa said he has always been careful not to be That Guy — the kind of grandparent who stuffs candy in the mouths of the grands between meals, and then professes amazement that they aren’t hungry when dinner is served.

“I never spoil them. I never have. I never would,” he said.

So what’s the beef? There are several.

He corrects the behavior of the grands (ages 8, 6 and 4). Sometimes, it’s too much for them to handle.

For example, Grandpa told the group, when he is the only adult around, he will sentence one of the kids to time out for hitting one of his siblings.

But their parents don’t believe in time outs. They believe in confronting the offending child as if he were a reasonable human. They make him apologize to whichever sib he has mistreated.

Time outs are for day cares, the son has told the grandpa. And his kids are past day care.

For another example, the dinner table.

If the four-year-old fails to put his napkin in his lap, Grandpa will remove his plate until he does it.

But the parents don’t do any such thing. They will wheedle, cajole and semi-beg the kid to put nap in lap. They claim it works, always, although not always right away.

And then, the third rail of all family conflict: money.

Grandpa ends every visit with his grands by handing each of them a crisp dollar bill. The kids have gotten so used to this that before they kiss him goodbye, they each stick out a hand, palm up.

The parents scream bloody murder about this one.

They insist that money is the province of the parents — to have, to hold, to withhold, at least until allowances kick in (they haven’t yet).

They accuse Grandpa of trying to buy affection. Grandpa says he’s merely trying to underscore the affection he already feels.

The parents have demanded that he stop with the bucks. He refuses. An epic family rupture is on the horizon.

As usual, every member of the Grumpy Grandpa Group talks at once.

You’re a loon!

You’re trying to invalidate the parents!

Your job is to support the parents, not try to replace them!

And the money business! Can’t you see why this smacks of bribery?

Grandpa was willing to listen to all of it. Then he played his ace of trumps.

When he was a little boy, this grandpa said, his grandfather used to say goodbye in a similar way.

He would shake the hand of his grandson. Inside the shake was always a dollar bill, folded so many times that it was the size of a mint.

“I don’t hand over the dollars with a handshake,” he told the group. “But every time I hand over a dollar, I think of my old cranky Gramps, long, long ago.”

The most brilliant member of the group — I shave his face regularly — pointed out that Grandpa had just resolved his own dilemma.

“Tell the parents about your cranky Gramps, and how he would say goodbye. Then tell the kids. Then make that tradition your tradition.”

At the next meeting, good news cascaded from the guy who was once on the verge of being a family outcast.

“Now,” he said, “I shake with each of the kids. They each get a dollar that way, folded to within an inch of its life. Subtle. Classy. Problem solved.”

These grands have just learned a lesson that goes far beyond naps-in-laps. They have learned that Grandpa has great memories to share.

That’s worth far more than a buck a visit.

Bob Levey is a national award-winning columnist.

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