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Squirreling Gone Wild #19: Well Played, Mr. Waiter

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Flattery, as we know, is an age old tactic to gain favor with people. Whether it’s for business purposes, to win over a date, or to curry favor with someone you want to impress, flattery is often used in order to reach a specific outcome.

This edition of Squirreling Gone Wild, the 19th in the series, is about a waiter who used a little flattery to obtain a nice tip from his customers. Much like the Crafty Waitress from Squirreling Gone Wild #16, this person employed some George Costanza-like methods to earn a few extra dollars from paying customers.

This story comes via a friend of mine, who recently went out to dinner with his wife. I have known them both for many years, him a few more. Needless to say, I know them pretty well.

He recently sent me a random text, which he does on occasion. They tend be on sports, stocks, careers, or other random topics of interest to him aside from his main interest: his family. This time, however, the text was related to his family, specifically his wife.

The text read: “Waiter asked Elaine to see ID, I told her it’s just for more tip. Would you ever say something like that?”

I smiled when I read that, because it sounds just like him. First, I told him no, I probably wouldn’t say that. I might think something like that, but would probably keep the thought to myself.

The next time we talked, which was a few days later, I asked him what exactly happened.

Apparently, when the waiter came by to take their order, they ordered cocktails. The guy asked Elaine (not her actual name, but let’s go with it here) for her ID. Now, Elaine is in her late 30’s. She does look younger than her age and is a very fit, active, nutrition-conscious person. But someone in his or her late 30’s will not look like a borderline-21 year old person. I don’t know any contemporaries that do, and have yet to meet one. We all age, it’s natural and normal.

According to my friend, it made his wife beam with pride. She was teasing him how she was carded and he wasn’t, though she’s a few months older. That’s when he told her that the only reason the waiter did that is in order to flatter her so he can get a bigger tip.

I of course started to laugh when I heard that, because I know my friend and how he can be direct, a bit competitive….and have the ability to accurately assess situations. So, he said that to her. Personally, I wouldn’t have said that, and would have let her enjoy the moment, no matter how delusional. But hey, we’re all different.

Then I asked what she said, and he evaded the answer a bit, changing the subject to what the waiter ended up doing. Apparently, the waiter went to a table of two guys in the booth adjacent to them, and took their drink order without asking for IDs. The guys seemed like a father-son duo according to my friend, about 55 and 25. The son was a younger looking guy, but was not carded. My friend’s wife, who is actually well over 10 years older, was carded.

Needless to say, this fueled my friend’s suspicions even further. He told his wife this again, teasing her, and she talked some smack beck at him. All good natured, I’m sure.

He said that they later both noticed a different larger table of women, seemingly out for a “girls night”, get carded by the same guy. Then my friend’s wife started to buy in a bit, but still rubbed it in his face that she was carded and he wasn’t.

Later, when she got up to use the restroom, the bill came and my friend told the waiter that the guy made his wife’s week by asking for her ID. He also said that it made her happy to see that she was carded and he wasn’t, in addition to the younger guy at the adjacent booth.

So my friend, while bantering back and forth with the server, joked with him by asking him “If it works”. The waiter apparently paused, thought about the question for a second, and said with a gleam in his eye and a smirk on his face, “I’m in the business of making people happy”.

When Elaine got back to the table, my friend said he was looking at the bill and trying to figure out a tip. She told him to give him an over the top nice tip.

Well played, Mr. Waiter. Like a squirrel trying to find a nut, he kept at it and ultimately got his modest prize.

My friend dutifully did what his wife asked him to do, and gave the guy a good tip. I’ll give him credit for admitting it. I didn’t ask what percentage, but he felt that the waiter deserved credit for being smart, and besides – his wife told him to do it:)

Have you ever experienced anybody – be it a sales person, vendor, waiter – flattering you in an obvious way to try to get money from you?


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