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

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?


  1. says

    “I’m in the business of making people happy”.

    Now there’s a guy who’s figured out his value proposition. He’s not in the business of bringing food to strangers. Nothing wrong with flattery, if used judiciously.

    • Squirrelers says

      @101centavos – well stated, he has figured out his value proposition. Rather than be a run-of-the-mill server, he’s found a way to connect with the customer and differentiate himself in a good way. Smart guy.

    • Squirrelers says

      Nicole – this is why I stated that I wouldn’t have said what he said, and let her enjoy the moment even if delusional :)

  2. says

    Excellent! The waiter obviously knows more about how to get good tips than the previous waitress featured.
    We all know women want to look younger and why shouldn’t we flatter them a bit if it makes life easier. :)
    Everybody is happy, it’s a win win situation.

    • Squirrelers says

      @retirebyforty – that’s funny, “makes life easier”. Of course, if the tables were turned, and it was a waitress trying to charm a male customer, we both know that most guys can be suckered easier when it comes to tipping. I don’t think that’s the case with me now, but when younger it could have been. That’s part of what’s funny to me about this particular episode

  3. says

    I hate getting carded since I’m 27 and people seem to assume I’m 17 or so. They’ve even given my husband dirty looks for taking me out (I’m 6 months older than him). Poor guy. So that poor waiter would have accidentally ticked me off, lol. Personally, if I was a waitress, I’d use a proper arsenal of humor and smiles to get good tips. At $2.13 an hour, they need them.

    • Squirrelers says

      Crystal – you make a great point. At such an abysmally low wage, they DO need tips. That’s why I cringe when I hear of people who don’t leave tips unless the service is great. Tipping is vital for these people. As I’ve mentioned elsewhere, I typically give 15% to 20%. As for being carded, I have to be straight up here, and say that I would like it if it happened again! I’m in my late 30’s, so it’s stopped now, but up until my early 30’s I was getting carded on occasion. I don’t even think the motives were the same as with the waitress here. I did have someone in her 20’s, at a professional happy hour, tell me she thought I was just a few years out of college. I guess the dim lights must have hid the emerging gray in my hair, especially by the temples. I think I look about my age now. You never know, perhaps some people can miss all the cues and just don’t have a sense of things.

  4. says

    You never met a woman who is in her late 30s and looks like she barely turned 20? Well… you never met me! LOL Just kidding… My husband and I always joke about waiters who try to make some extra tip by asking me for an ID. It happens to me now and then but never works because I know how I look (not old but not 18 either) and I am a horrible tipper. My husband was a waiter for years and he knows all the tricks. But, on the other hand, if played subtly, it can be flattering…

  5. says

    I wonder if this ever backfires on the waiter. What if Elaine didn’t have her ID? Plenty of times my girlfriend and I go out and she leaves her wallet in the car or at home. Would the waiter deny Elaine a drink, or just smile and realize his bluff has been inadvertently called?

    • Squirrelers says

      Greg – good point, this can backfire on him. What does he do in that case, when the woman has no ID on her? Maybe’s he’s figured it out, and the benefits outweight the risks?

  6. says

    The waiter deserved the good tip. I’m sure it’s not the only trick he does. It sounds like he’s the type of guy who looks for opportunities to present themselves and capitalizes on them.

    I was a waitress for years. My thing is that I had a lot of regular customers. I knew many of them by name and I think they liked that “Cheers” personal touch.

    • Squirrelers says

      First Gen – I can see how that would be appealing for a lot of people, that “Cheers” personal touch where they know your name. I guess for me it would depend on the place…it might be cool at some places, while at a few others I might not like it to the point of avoiding the place. Sometimes personal connections are good, other times anonymity is good…

  7. says

    So did your friend ever tell his wife that the waiter ‘confessed’? (I hope not!)

    You know what? I see nothing wrong with it. He is in the business of making people happy- he made the woman happy, and himself happy with the big tip. It is no different than the salesman drinking with his prospective client to get business.

    Who couldn’t use a little flattery to make their day a little better? Of course, it has to be done well. You don’t want to card the 75 year old botox-laden woman, but why not card someone who is trying to look nice? Takes no effort, and makes someone happy.

  8. says

    I’ve seen my grandfather in action too many times to fall for that type of behavior (he was a store owner and a natural salesman).

    I like this waiter much better than the waitress that tried to rip you off! She was just flat out deceitful!

    At least the waiter is making people happy. If they fall for it, good, if not… he still might feel okay about it. After all, it just cost him a few kind words and a smile. And if the waiter is smart, I would say the same thing to your male friend (perhaps it even made your male friend feel smarter). He didn’t want your friend to think he was hitting on your friends wife.

    Sounds like a great waiter really. :)

  9. says

    Haha, something weird happened to me last year when I was literally pulled over by a couple of girls to look at some Seacret products and try them, and they smooth-talked me and almost tricked me into buying a bunch of packs then, but I escaped. I ended up going back and buying some anyways since they were on special. 😉

    • Squirrelers says

      Invest it Wisely – I once got smooth talked into buying something from a mall kiosk, years ago, by some charming girl. Not much money was spent, but I learned a real lesson there, and it hasn’t happened again.

  10. says

    The servers point was right on. He’s in the business of making people happy. He was doing his job- Bravo!
    In my state you must card if you look over the age of 30. I scared a server one time when I was 29 and he didn’t card me. I yelled out, ‘Do I look like I’m 30?’ I was kidding but once I said it I realized it was not a very nice joke. He was so apologetic and than I started apologizing. It was a mess all around!

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