John Y’s Musings from the Middle: Big Shot on a Budget? Total FAIL

Every month I have dinner with a wonderful group of guys. We usually each pay for our own dinner but every few months someone feels a call to pick up the ticket for everyone. I felt the call about three months ago but didn’t pick up the check at the time but did announce to the group I would be doing so sometime in the near future .

Tonight was to be that night.

Sort of, anyway.

As we were finishing dinner, I furtively slipped by the cashier and asked how much our table’s dinner would be because I “may” be picking up the check. The cashier pointed to a much higher figure than I had imagined and explained that a 15 % gratuity was automatically added since there were over 7 of us. I told her I would not be picking up the check this time after all but maybe would buy dessert for the table.

The dessert menu was described to the table and no one ordered anything.

Hmmmm. Now what ?

And like a brilliant thunderbolt crashing through my brain, I suddenly had an ingenious and novel idea!

I went back to the cashier and said, “Look, how about I pay for 25% of the bill? Can you work that out for me?”

The cashier politely said it shouldn’t be a problem but added that no one had ever made that request before. “How would that work ? ” she asked.

“Well,” I said, “Just take 25% off the top and charge everyone else only 75% of their meal.” I looked at her incredulously like this is something that is requested all the time in large groups where the big shot is also fiscally prudent.

A few minutes later she came by the time and whispered in my ear, “Does that 25% off the top include the tip?”

“Yes,” I said. “Look, just charge me one-quarter of the total price and divide up the remainder evenly–including the tip.”

At this point the person next to me said , “Just give me the check. I’ll cover it.”

I insisted I pay 25% and a small big shot verbal scuffle over the bill ensued. “Oh, are you serious about getting 25% of the tab? I thought you were joking.”

“I am completely serious,” I exclaimed, hoping someone else at the table would notice. “Why don’t you pick up the remainder, whatever that is, like….oh,  75%?” And he did.

I announced to the table that although I wasn’t picking up the entire tab (because it was too expensive) that I I was covering 25% –which was worth noting. And added that I was glad one person who was supposed to attend had cancelled. “That’s 25% of one meal I didn’t have to cover.” I then added I would be picking up 10% of a meal this summer and up to 20% of a meal in the fall so that I would incrementally pick up 100% of one of our group dinners…but was going to stretch it out over an 18 month period of time.

But as we shook hands and said goodbye until next month’s dinner everyone was thanking my friend for dinner and not giving me an honorable mention but instead a quizzical or bemused look when I explained again how we had divided things up.

Finally, with the last friend to say goodnight I simplified it by explaining the situation more concretely. “You know those au gratin potatoes you had tonight? Well, I paid for them. The entree, drink, and salad was picked up by someone else. So just thank me for the au gratin potatoes.”

And that was that. I spent more than I had planned to appear to be a big shot and looked cheaper than ever.

But learned a valuable lesson. When trying to impress by offering to pay for dinner it never works to try to do it a la carte. It’s an all or nothing proposition. Like most things in life.

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John Y.’s Video Flashback (1995):