my boss is a terrible restaurant guest

A reader writes:

I’ve worked for my C-Suite boss for almost five years. We are in a line of work where we attend a lot of lunches and dinners at nice restaurants, most often as guests of vendors and clients. While I generally enjoy the fine dining opportunities, I find my boss to be an insufferable restaurant patron.

My boss considers herself a “foodie” so she is often the one who suggests a restaurant for these meals; she prefers to go to places she has not been before when someone else is paying. She rarely deems a restaurant good enough to go back to more than once!

Like clockwork, at the beginning of every meal she peruses the drink menu, announces that nothing sounds good, and asks the bartender to make her something off-menu (usually with lots of instructions and ingredients). Without fail, she does not like that custom drink and sends it back in a way that implies that the server didn’t take all of her instructions or the bartender is bad at his job.

She often complains loudly that a dish is missing “something” or another vague criticism, and if she’s loud enough for the server to overhear and inquire, she asks for the dish to be removed from the bill. If the server isn’t paying as much attention as she would like, she comments to the table about how the tip should be lowered (particularly cringy when we are not the ones paying).

Instead of ordering dessert, she will start her meal over and order a cocktail and appetizer while everyone else drinks espresso, a move that usually confuses our dining companions and also can throw off the servers, not to mention it extends the meal another 30 minutes or longer just when we were close to wrapping things up.

Admittedly, I may be more sensitive to her particularities because I waited tables in a high end restaurant to support myself through high school and college. That experience has trained me to be a much more gracious, patient diner and to be a lot more forgiving when things aren’t perfect.

However, I find it so embarrassing to eat with her that I’ve been turning down invitations (and missing some important networking opportunities). While I know her poor manners are a reflection on her and not me, I have noticed that our hosts are more frequently asking for me to pick a restaurant I think she’d find “acceptable” or suggesting that we “skip the meal this time.” So I get the feeling others have picked up on this as well. Should I say something to her?

Your boss is an ass!

Her behavior would be boorish in any circumstances, but particularly in a business context (where there’s generally an assumption you’ll overlook small issues because the food isn’t the point of why you’re there) and particularly when someone else is paying (because her behavior conveys that the host’s choices have displeased her). But even if this weren’t a business context and/or she were the one paying, her behavior would be rude — and mortifying to any decent person she was with.

As for what to do … what’s your relationship with your boss like and how does she take feedback generally? Would she be open to something like, “I think Lucinda and Jeff were embarrassed that you seemed so unhappy with the food and service” or “I think it made them uncomfortable when you kept sending the drinks back”? Or even a more direct, “Contacts have been suggesting we skip dining recently, and I think they’ve noticed you’re often unhappy with the food and service” or “When you criticize the restaurant, people we’re eating with get uncomfortable — it’s landing like you’re criticizing their hospitality”?

If you think she’d be willing to hear that — and, importantly, if she’s generally a reasonable person when she’s not dining out — you could give that a try. But I’m skeptical that she’ll be open to hearing it; people who behave this way are usually eager to tell you why they’re justified, and you’ll probably be inviting a rant about bad service.

Most likely, you’re better off reminding yourself that your boss’s behavior really doesn’t reflect on you. You’re not the one sending back drinks or berating the server, and people aren’t going think you endorse her actions; they’re aware of the power dynamics in play (and it sounds like they’re subject to them a bit themselves too). If you really want to underscore that, you could mention how much you enjoyed your meal or how delicious your appetizer is — but even if you don’t, it’s likely to be clear that you don’t stand with your boss on this stuff. You could also make a point of warmly thanking the server, or even going out of your way to find them as you head to the bathroom and thanking them for their patience or saying that the rest of you are enjoying the food. The subtext will be clear.

{ 445 comments… read them below }

  1. Filthy Vulgar Mercenary*

    I know normally anonymous notes are a terrible idea. Would this be a place for anonymous notes, though?

    1. D*

      I’m curious about your thinking here. How would an anonymous note help when speaking with attribution would not, and is it even likely that someone else in the organization could have left it? It sounds like their other dining partners are generally outside partners.

    2. wondermint*

      Hm.. probably not. It’s unclear how many of LW’s boss’ colleagues attend these meetings, but if its just a few (or only LW themself) it could be pretty obvious who wrote the note.

      I like taking the angle of “it’s making our hosts uncomfortable” rather than “you’re a jerk for acting this way.” An anonymous note exaggerates the latter.

    3. Jessica*

      Absolutely not. Anonymous notes create mistrust, paranoia, and widespread blight on relationships. The recipient isn’t thinking about the problem that you were trying to get their attention on, they’re thinking about who sent the note, and reviewing in their mind every single person it could possibly have been. It’s a terrible experience, and highly unlikely to accomplish anything.
      If the break room freezer is full of severed heads and you’re concerned that your boss may be a serial killer, sure, call the FBI’s anonymous tipline. But don’t send an anonymous note about ordinary workplace bad behavior.

      1. Lime green Pacer*

        I’m mentally substituting “social media” for “anonymous notes” and getting a whole new perspective on FB etc.

      2. Bananapantsfeelings*

        “If the break room freezer is full of severed heads and you’re concerned that your boss may be a serial killer, sure, call the FBI’s anonymous tipline.”

        Well NOW you tell me!

        1. too little too late*

          I cleaned and sanitized the freezer two weeks ago, and *now* you tell me.

      3. AW*

        My field of work includes anonymous peer reviews and I can confirm I now view a lot of my colleagues with distrust after I received a blatantly out of line, clearly biased review (it was MUCH different than the other two reviewers comments). I ruminated for several days about who could have done this (there’s only about 10 of us), have come up with 1-2 likely possibilities, and I haven’t been able to shake the feeling of distrust I have towards them since.

        Anonymous is almost never the answer.

    4. Falling Diphthong*

      Why would the boss believe the anonymous note was anything other than a reprehensible stranger launching a cruel attack, which is discounted because the speaker has no credibility?

      This is a sincere question.

      Alternatively there’s an excellent chance that it’s obvious to her who sent it anonymously, which makes OP look terrible and moves the question over to OP’s judgment in sending anonymous notes.

    5. Pastor Petty Labelle*

      Why would boss listen to an anonymous note? She’s a foodie, she is just making sure everything is up to her standards, there’s nothing to criticize about her behavior. According to her, of course.

    6. Person from the Resume*

      Who could the anonymous note come from except the LW?

      She dines with her boss and external partners.

    7. Falling Diphthong*

      Reasonable uses of anonymous notes:
      • Wet Paint
      • I turned off the sound on this phone that kept going off.
      • Found: Hello Kitty as The Girl from The Ring charm

      It’s giving information about the environment, not about the writer’s judgment of someone’s personal shortcomings. (Though that might be implied in two.)

      As soon as you’re judging someone’s bad behavior, their immediate response is going to be “Who are YOU to judge ME?” On rare occasions the answer is “Someone whom I really respect, who usually doesn’t criticize my decisions, so I guess I am going to listen and take this to heart.” As soon as it’s anonymous, the assumption is that the anonymity is because it’s an unreasonable rage ball whom no one would take seriously.

      1. Filthy Vulgar Mercenary*

        All good points…I think I had so little faith that the LW could successfully bring this up to the boss due to the boss’s attitude, combined with such an intense desire for the boss to stop being such an amazing jerk, that my mind was trying to find other ways to make sure boss still got the message.

        1. Raisin Walking to the Moon*

          I’m actually a reluctant fan of the anonymous note! I only used it once, after face-to-face with BoD hadn’t changed anything, and it worked dramatically.

      2. Queen Anon*

        Now I kind of want to see a Hello Kitty as the Girl from the Ring charm. can Hello Kitty be threatening and terrifying?

        1. MigraineMonth*

          Yes. I think horror is a lot more about context than the actual subject. There are horror films about cabins in the woods, dolls or puppets, clowns, twin girls in matching outfits, summer camp, hockey masks, crying babies; all pretty normal everyday things that are made scary by the films rather than being inherently scary themselves. So yeah, I think a Hello Kitty-themed serial killer could be terrifying.

          For that matter, what’s terrifying about videos and soaked women with long black hair?

    8. Nah*

      Not gonna lie, I thought you meant a note for the server/kitchen staff and was wondering why it needed to be anonymous.

      (My family have actually sent a few of these before, Grandpa had some (at the time unknown about) unaddressed health issues and could be a right snit to the less-than-minimum-wage wait staff on the rare occasions we went to restaurants together. Obviously we always tried to shut it down the best we could, but also sometimes ended up sneaking an extra tip and apology on some spare notepaper.)

    9. Beth*

      Probably not. How many people are joining the C-suite boss for these meals regularly enough to see the pattern? It’s likely to be too small a group for anonymity to really protect OP.

      The bigger opening I see here is that hosts are actively asking OP to suggest a restaurant the boss likes or asking to skip the meal entirely. Telling your boss that you think she has terrible manners is a hard thing to do. Passing on the message “the host has asked for a restaurant where you already know you like the food and service, what would you suggest?” The implication that she behaved badly might still not go over well, but at least it’s not OP’s opinion anymore.

      1. Filthy Vulgar Mercenary*

        “ the host has asked for a restaurant where you already know you like the food and service, what would you suggest?”

        Such a great idea.

          1. Ellie*

            If there aren’t, that might be the push needed to recognise her own behaviour. It’s also a great lead-in to, ‘shall we skip the meal portion then?’.

            The above is excellent wording and is worth a shot. Some people double-down when called out, but go away and think about it later, and their behaviour improves.

  2. Observer*

    Is there some way you can comment positively on her being a “foodie” while pointing out that business meetings are not the forum for extending her avocation? Like she wouldn’t get into her stamp collecting hobby with business contacts, even though stamp collecting does actually require quite a bit of knowledge.

    Same here. (In theory) being a foodie requires some understanding of food and a discriminating taste. But that’s her personal hobby, and business meetings are not the time for that.

    Of course that depends on your boss having *some* level of reasonableness. Which, who knows, because her behavior is so out of line. Is she generally someone who builds herself up by tearing others down or goes on power trips? That’s what this sounds like, to be honest.

    1. dulcinea47*

      I don’t think she’s a foodie, even. Or else she thinks that being snobby & rude is what a foodie does.

      1. Anonym*

        Yeah, I think she’s more inconsiderate jerk than foodie. The latter designation is just the excuse she’s using for being obnoxious.

      2. br_612*

        I think you hit the nail on the head. She thinks being pretentious and ostentatiously pickier than my brother (who didn’t eat burgers until he was 12 or anything with noodles until he was 16) makes her a foodie. When really it just makes her an ass.

        Plenty of self-proclaimed foodies are still kind to waitstaff, and understand that not every restaurant is for them and their personal taste.

        1. MsM*

          In fact, I feel like a lot of the top Michelin star restaurants follow a philosophy of “you’ll eat what the chef feels like making in the order they feel like making it.”

        2. Observer*

          She thinks being pretentious and ostentatiously pickier than my brother (who didn’t eat burgers until he was 12 or anything with noodles until he was 16) makes her a foodie. When really it just makes her an ass.

          Absolutely. That’s why the LW might need to butter her up by acting as though she’s really so smart, but this is just not the time and place for her genius.

        3. Bananapantsfeelings*

          I don’t actually know true foodies who don’t return to *any* restaurant.

          True foodies get OBSESSED with really good restaurants, and often spend days/months/years trying to recreate that incredible menu item at home.

          There’s a saying: “Those who use brutal honesty enjoy the brutality more than the honesty.” That’s who she is.

          1. goddessoftransitory*

            That’s the late Vincent Price to a tee. He and his wife wrote a huge cookbook about French dishes back when only Julia Child was doing anything of the kind, and his daughter wrote in the introduction of the reissue that he had spent weeks working on his creme’ brulee’: “After a week my jeans no longer fit and I realized why my mother had retired as his taster.”

            Price was also by all accounts a charming gentleman who is the exact OPPOSITE of the behavior described!

          2. AnalogMayhem*

            Thank you for reminding me of the saying “Those who use brutal honesty enjoy the brutality more than the honesty.”

            That statement comes in second to “We’re like a family” in the workplace. If you hear anyone near you say “We’re just brutally honest” or “I’m just being honest,” you should probably start updating your resume.

      3. Falling Diphthong*

        I think the hobby is play-acting being a foodie. But that OP should not use that framing.

      4. Miette*

        Hard agree. Being a foodie means being enthusiastic about all aspects of the experience, from the dish to the ingredients chosen/presented to the story the menu is designed to tell. Being rude and demanding is just bad manners and not at all a part of it. Pretentious and insufferable probably LOL, but rude and demanding no.

      5. OMG, Bees!*

        I’m curious if the boss is doing this for show during a work lunch and maybe isn’t this problematic with meals privately

    2. pally*

      I would think that, as a foodie, the boss would know at least a few restaurants where she does enjoy the food (i.e. a “go-to” list of places where she like to dine).
      Hence, maybe asking boss to recommend one of these places would improve the chances of the boss conducting herself in an acceptable manner.

      Just have to disabuse the boss of trying out new places for business meals.

      1. Pastor Petty Labelle*

        Boss picks the restaurant and does not go to where she knows she enjoys the food. Because I doubt she enjoys anywhere. Her whole schtick is being pretentious to show how much she knows about food.

        I would not be surprised she knows better than to repeat a place because she knows she will get terrible service due to her previous behavior. Wait Staff remember.

        1. Mark This Confidential And Leave It Laying Around*

          I doubt this one tips, either! This behavior is one-and-done.

          1. OMG, Bees!*

            Oh yeah, this also screams the type of behavior to intimidate the staff and make them comp part of the meal to appease her. Which makes it extra weird given that she doesn’t have to pay for it.

        2. Moira's Rose's Garden*

          Since she’s doing stuff like asking to have meals and I assume drinks, since she sends those back too, taken off the bill, I guarantee front of house and management remember her too.

          You give a new customer benefit of the doubt on that isht ONCE. The same party does it the next time? Well, I’ve seen that management varies on whether the black-list is formal or informal, but you betcha things like rezzies are getting declined, seating will be a long wait for a terrible table, and worst case is some head chef’s will come tableside and throw your ass out.

      2. Hlao-roo*

        I think you might be on to something here. Maybe the OP could try something along the lines of “the past few lunches we went to ended up being pretty disappointing experiences, food-wise. [Recent restaurant name] couldn’t even make the cocktail you asked for! Are there any restaurants you’ve been to that have excellent [food/service/drink menus]? You have such great taste and eating at a proven restaurant would really impress our [clients/vendors] and help strengthen relationships.”

        I’m not great with word-smithing, but hopefully that gets across the basic idea that by playing into the boss’s idea that she’s a great foodie and flattering her ego, the OP might persuade her to choose restaurants where she won’t behave like a total boor.

        1. Pastor Petty Labelle*

          Boss’ reaction will be — no they are all terrible, let’s try someplace new, maybe they won’t be terrible.

          Narrator: Boss, in fact, decided they were terrible.

          Boss is not going to suddenly see the errors of their ways with just the right magic words. Boss sucks and is not going to change. All OP can do is distance herself from boss’ behavior.

        2. Broadway Duchess*

          Ordinarily, I hate playing into this kind of thing, but I think it could be the way to go in this case. Boss strikes me as overly committed to this misplaced idea of a goodie being so discriminating that she just can’t help being an ass. People like this are usually not given to self-reflection, so being honest could backfire on LW. Playing into her purported expertise could achieve the goal of not spending another embarrassing meal with her and not pissing her off, either.

      3. sparkle emoji*

        It sounds like she’s already picking currently and just choosing new places because that’s what she wants. I’m not sure hinting from OP will send her the message that she needs to stop using business meals to sample, this manager seems obtuse. Maybe if the clients start being more explicit to her?

        1. Six for the truth over solace in lies*

          I think she’s choosing new places because she’s aware that she’s incredibly picky and hates 99% of everything (though I imagine she thinks of herself as “discerning”), and doesn’t want to pay her own money to try a place she knows she’ll probably hate. I suspect that she does have places she likes, and only goes to them when she’s paying for herself.

          1. WellRed*

            I don’t read it as picky so much as rudeness to the wait staff and the hosts. She probably stiffs under drivers on tips, too!

            1. Six for the truth over solace in lies*

              It’s clearly beyond rude, wherever she does it. I was responding to the question of why she chooses these new places rather than places she knows she likes.

            2. JustaTech*

              She sounds like someone that Tim Gunn described meeting, a teen socialite who sent back a dish at a fancy restaurant not because there was actually anything wrong with it but “to create drama”.

              I had a classmate like this in college (a guy) who, the one time we went out to a sit-down restaurant asked for so many extra things that we got our food a full 30 minutes after the rest of our group. (He was at least polite and charming.) At least in that case we could just never invite him again because he was so dang arrogant. Can’t do that with the boss (sadly).

          2. Nah*

            Or could also be constantly choosing new places because at least some of the other ones have put her on a ‘Do Not Serve’ List. Not necessarily for the abuse towards staff (alas, but money often talks more than staff walking does) but someone trying to comp every single item they order is almost certainly going on the manager/owner’s radar.

          3. Typity*

            It sounds like she walks into new places expecting to hate them, since that’s part of the fun for her. It says, “I am more sensitive and discriminating than anybody who actually likes this stuff.”

            She’s using her job as a means of indulging herself in more and better restaurants, and on someone else’s dime. Whatever she thinks she’s proving, she’s being very rude to her hosts as well as the restaurant staff.

          4. tangerineRose*

            I’m a picky eater and a vegetarian, but restaurants usually have a decent selection, and I can almost always find something to eat. This doesn’t make me rude the the waitstaff.

            I think people who are rude to the waitstaff for no reason are on some kind of power trip.

            1. actual cat herder*

              yeah i have a combo of food allergies & ARFID, most people would consider me picky, but i know how to behave in a restaurant even if there isn’t something i can eat?? this is just rudeness

              1. JustaTech*

                Seriously. More than once I’ve put up with food that was only borderline edible by me (way too spicy) because the person in front of me in line was *so* rude to the staff that I just couldn’t bear the idea of piling on, even though my complaint was reasonable.

      4. HD*

        If she’s sending food back and/or trying to get it comped, there’s probably a reason she won’t go to the same place twice.

      5. Slytherin*

        I wonder if she never goes to the same place twice because she keeps getting banned from restaurants?

    3. MigraineMonth*

      That’s an interesting framing. I’m not sure if it would work, but I’m not sure if any of these will work; they all depend on her being a level of reasonable.

      1. Observer*

        That’s the real problem, isn’t it. :(

        She does not sound like she is AT ALL reasonable, so I’m not really hopeful.

        My thinking was that at least if it doesn’t work, it won’t offend the boss so hard that she’ll take it out on the LW.

    4. I'm here for the cats*

      I don’t think this is a foodie thing. This reads to me like she’s really in it to neg and to control. Saying this because I’m food mad, I also have odd palette (I absolutely detest sugar in my food or drinks), and I go out of my way to avoid professional meals because how much it could potentially either be me suffering or me making others uneasy.

      I really found this boss both intentionally unpleasant, and really not that socially intelligent.

      1. WestsideStory*

        My take on this – boss is being treated by vendor or client: she’s using the meals to emphasize that she is a “tough customer” and very likely is as picky with them as far as work deliverables etc – using it as leverage to get discounts or add-ons or extra work for free.
        It sounds like the hosts get enough of her in negotiations that they don’t want their lunches ruined as well.

  3. Alton Brown's Evil Twin*

    Yikes. And it’s not like you could call the restaurant in advance and give them a heads-up that your boss is… not a normal diner.

    I’ve seen advice from restaurant reviewers about doing this kind of leg-work: provide your credit card in advance if another member of the party is going to try to grab the check, let the staff know that you need to be seated close to whatever because of an accommodation or a quirk, allergy warnings, etc.

    But how do you let them know in advance that your boss is going to pull a power play with drinks, or order an appetizer for dessert, without the result being that they give you worse service, not better? Especially since your boss isn’t even the one paying! OP I am cringing in sympathy with you.

    1. MsM*

      Honestly, I think the restaurant should have the ability to do whatever the restaurant needs to do to mitigate the situation, whether that’s having the manager oversee the table or just being aware that nothing they do is going to be right and focusing on the customers who do appreciate their efforts. Maybe if someone actually declines to serve her, she’ll start dialing it back.

      The better bet might just be OP suggesting options for client/vendor meetings that don’t involve sit-down dining, though. Or using the networking opportunities to focus on finding out who else is hiring.

      1. MigraineMonth*

        It sounds like clients/vendors are already avoiding sit-down meals with her. After just one of these performances, I would only do delivery with this person.

      2. tangerineRose*

        I wonder if the boss just likes treating people badly when she thinks she can get away with it.

    2. Sparkles McFadden*

      It actually is possible to do this. The hard part is being discreet. Maybe just look for the restroom and tell whoever’s in charge at the restaurant that a member of the party may be difficult.

      I worked for a boss who was generally good, but just a total jerk in restaurants. I also had a coworker who was a self-proclaimed foodie who would do stuff like insisting we all wait until he’d held his entree in one hand and fanned the aroma of the food towards his nose while he closed his eyes, sniffed dramatically and announced that the dish didn’t have enough turmeric or some such nonsense. So, I’d find some way to talk to the maitre d’ and explain that my boss was a loud jerk and my coworker was a horse’s ass and that I was profoundly sorry for what was about to happen. The maitre d’ would warn the waitstaff and would intervene when my boss got too loud or when the foodie coworker would insist on something ridiculous, like talking to the chef directly before he ordered.

      This sort of second-hand embarrassment happened at work as well and was one of the reasons I eventually moved to another department.

      1. Sack of Benevolent Trash Marsupials*

        Oh my! @Sparkles, I am cringing so hard for you but also I admit I laughed out loud. Also, +1000 because definitely having TWO horses’ asses at the table would be something I’d find a way to warn staff about.

      2. Policy Wonk*

        “So, I’d find some way to talk to the maitre d’ and explain that my boss was a loud jerk and my coworker was a horse’s ass and that I was profoundly sorry for what was about to happen.”

        I snort laughed at my desk. I needed that today, so thank you lol

      3. Le Sigh*

        “I also had a coworker who was a self-proclaimed foodie who would do stuff like insisting we all wait until he’d held his entree in one hand and fanned the aroma of the food towards his nose while he closed his eyes, sniffed dramatically and announced that the dish didn’t have enough turmeric or some such nonsense.”

        I commend you for having the strength not to push the plate of food right into his face.

        1. Spring*

          I’ve found that, as I age, I give fewer and fewer f*cks, so if a colleague tried this, I would probably laugh at them and start eating.

        2. Sparkles McFadden*

          I stayed quiet and paid close attention in order to memorize every move he made so I could reenact this horrible dining event for family and (non-work) friends at a later date.

      4. Grumpy Elder Millennial*

        I’ve never worked in a restaurant, but this seems like a good thing to do if you can. If nothing else, the maitre d’ and/or other management can be prepared to intervene if necessary. Like, they’d have a heads up that things are likely to go sideways and be ready to shift to plan b.

    3. Another Academic Librarian too*

      I think this would work. I have a business associate who is very careful (picky sounds pejorative) and not a jerk about it.
      I make sure when I select the restaurant I know they can support her needs, warn them and select one or two things off the menu that can be adapted. Even if someone else is paying I slip them an advance tip in cash (usually 2 twenties.)

      With the boss who seems like a jerk, maybe a pre fix menu for business meals. The fanciest restaurants can do that. Have the choices in advance. apologize for not being flexible. Blame previous discomfort with her “not having a satisfactory ” meal.

    4. frenchblue*

      Could you email the restaurant afterwards? I once had an aunt pick up a cake for a party. The cake was from an award-winning bakery and it was stunning. But for some reason, my (very uppity) aunt hated it, and ranted at the poor cashier about how it was all wrong and horrible. When I found out, I emailed the owner, thanked her profusely for the beautiful cake, and apologized for the confusion and ranting at pickup. I also let her know that I left her a 5-star Google review, and that I would always be happy to use her services and recommend her to friends. She was extremely grateful for the clarification, and I hope she also let her cashier know about the apology. I think advance notice would be better in OP’s case, but this could be an option as well, especially if the boss’s behavior is especially egregious. Sometimes, it can just be nice for managers to know their staff & food were definitely *not* the problem.

      1. Plate of Wings*

        You did the right thing! Great advice for LW. I know a lot of people who work in high-end specialty places like that bakery, it’s certainly not to get rich, and these cruel tirades aren’t easy for the employee or owner because your entire job is to give people a special crafted experience. If this makes sense for LW, I hope they see it.

  4. The Cosmic Avenger*

    Not only is she an 4$$, she is showing her whole 4$$ when she says that because she doesn’t like something about the kitchen’s work (the food missing “something” that she can never pin down), and she made more work for the server in sending it back AND take it off the bill, that the tip should be lowered instead of raised!

  5. Stretchy McGillicuddy*

    Call the restaurant in advance and tell them your group is coming for a business dinner and a member of your party is known for being difficult. They may be able to head some of this off at the pass if they know what is coming.

    Also, your boss doesn’t go to restaurants twice because she knows she would be unwelcome a second time.

      1. wondermint*

        Even this behavior at three or four restaurants is enough to establish it as a pattern.

        Omg, Stretchy, you’re so right about why she doesn’t go anywhere twice.

      2. Juicebox Hero*

        If they’re in a big city, it would be easy enough, albeit I’m sure plenty of those places wouldn’t want to have her in there twice. The places wouldn’t even have to be fine dining, just what Boss thinks have snob appeal.

        I don’t think she’s a foodie at all, because I’m a foodie who hangs with foodies and we don’t do that. She’s just got a bloated ego and wants to be Alex Guarnischelli on “Chopped”.

        1. Decima Dewey*

          Servers also move from restaurant to restaurant. I can imagine a server who’d dealt with boss before thinking “Oh, no. Not again! Please don’t seat her in my section. Please don’t seat her in my section…”

        1. Six for the truth over solace in lies*

          Especially given how frequently restaurants go out of business. There’s a spot near me where you could go to the same physical building three times in ten years and it would be a different “upscale Pacific Northwest farm-to-table fusion” each time.

      3. MBK*

        Depending on how frequent these dinners are, Chicago could probably support this horrible habit for years with no repeats.

    1. Bast*

      Yes, and maybe stick them with the head server, or one who doesn’t take crap. I remember my very first week serving I had the RUDEST guy come and sit in my section. He fancied himself Gordon Ramsay and critiqued everything from the french fries to the chocolate milk he requested with his cake at the end (and complained that we didn’t make our own desserts) to how slow he felt I was being (busy Saturday night, so yes, he did have a wait for his food). Seriously. I was brand new, not particularly extroverted, and left in tears. Give me 6 months and it wouldn’t have bothered me, but this boss sounds like a person you don’t sit in the newbie’s section.

      1. Spite Sweater*

        I had a similar experience and this lady complained to my supervisor who in the moment snapped at me but later apologized when she realized it wasn’t me it was the customer. The rest of the table could probably tell I had been in tears and were extra polite to me because they were clearly embarrassed by their friend and thankfully got the bill so I still had a decent tip.

    2. 3-Foot Tall Inflatable Rainbow Unicorn*

      Also, your boss doesn’t go to restaurants twice because she knows she would be unwelcome a second time.

      I caught that too – whatever fun the boss is getting out of this behavior, it’s apparently worth it to her to get serially blackballed from restaurants.

      What surprises me is that the vendors and clients put up with this. Boss has to be at the top of a very niche field for *them* to want to work with her twice!

      1. A Book about Metals*

        I can see vendors putting up with it if LW and boss work for a big account – they might figure dealing with annoying boss for a couple of hours is worth it if that keeps the account happy

      2. Orv*

        It’s possible she thinks this behavior impresses clients with how important and exacting she is.

      3. Observer*

        What surprises me is that the vendors and clients put up with this. Boss has to be at the top of a very niche field for *them* to want to work with her twice!

        Well, some of them seem to not be putting up with it – they are asking to not do a meal.

    3. Stretchy McGillicuddy*

      Adding to my own comment to add: You need to find one, or two at the most, restaurants to schedule all your business dinners. I think your boss is highly unlikely to be open to feedback about her behavior. If you are regulars at a specific restaurant, they will be better able to anticipate and accommodate her demands. She is going to push back on this plan. She is clearly using the business dinners as a way to explore your restaurant scene, but this is the one area you can have standing on. “These are business dinners, and it is much more conducive to business if we have a regular spot that we know works for us so we can focus on business instead of managing the waitstaff.”

      1. Luann*

        “She is clearly using the business dinners as a way to explore your restaurant scene, but this is the one area you can have standing on. “These are business dinners, and it is much more conducive to business if we have a regular spot that we know works for us so we can focus on business instead of managing the waitstaff.””

        As someone who has been in the host/vendor’s position for business meals, I suspect this boss thinks that the point of a business meal is to be (literally) wined and dined and made to feel special as the person in a position of power. If the actual business discussion isn’t happening because she’s so focused on the food the hosts are right to stop offering a meal since it doesn’t serve the business purpose. Honestly that might be the right move.

      2. HannahS*

        I completely agree with this! If the boss is someone who loves the DRAMA of being a difficult diner, then being at a familiar place will curb it somewhat (because it’s less fun to be dramatic when everyone already knows your deal.)

        The restaurant will also start to recognize what’s happening and have their own ways of mitigating it (place with an experienced server, internally roll their eyes and prepare the boss’ custom order.)

        OP, stop missing out on the networking! It’s one of the few benefits to you in this situation. Yes, it’s hard to watch someone behave that way, but it doesn’t reflect on you–rather, if you are polite, accommodating, and business-focused you will gain a good reputation as someone who can effectively manage a difficult executive.

        I get you–in your shoes, I’d also feel mortified–but it might also help YOU if you’re regulars. If you’re booking the restaurant, call ahead as others have suggested. As former waitstaff, you know what information to give to help them. Possibilities I can think of: one member will likely order off-menu; please place us with experienced waitstaff; one member will likely order an appetizer after dinner so take the coffee/dessert orders early.

      3. Observer*

        She is clearly using the business dinners as a way to explore your restaurant scene,

        Unlikely, I think. Because if she were trying to explore, she would be reasonable in at least SOME of the establishments. They cannot ALL be so terrible that she would never want to go back there.

        I think that she’s using these dinners as a way to throw her weight around at no cost and / or she’s trying to impress people with her pretentiousness, not realizing that she’s doing the reverse.

    4. Observer*

      <i.Also, your boss doesn’t go to restaurants twice because she knows she would be unwelcome a second time

      I suspect that this is also why she never suggests a place that she already knows. I would not be surprised if she does have a couple of places she actually likes, and wants to be able to go back to them. But she “can’t” use them for business dinners because that’s where she gets to throw her weight around with her pretentious phony foodie nonsense.

    5. Mockingjay*

      I was surprised how many high-end restaurants in my former city are owned by local consortiums. If you are blacklisted at one, you are blacklisted at the others. And servers who worked at a prior establishment when Foodie Boss came in, will remember her.

      As to advice: It’d be nice to broach the situation with Foodie Boss, but honestly, I don’t think Boss will recognize herself as the problem. Try to avoid scheduling “meal meetings” as much as possible.

  6. EtTuBananas*

    As someone who worked multiple service jobs (including serving) in their youth, someone else in the group acknowledging that the rude person’s behavior was, in fact, rude, goes a LONG way, emotionally.

    1. MicroManagered*

      I was a server for many years as well…

      … catching your server on the way back from the bathroom and slipping her an extra $5-10 bucks never hurts either! I used to do this when dining out with my ex-FIL because he was so unbearable. It was worth the money to me.

      1. MMR*

        It’s been over 15 years and I haven’t forgotten the very nasty women who was incredibly rude, insisted on paying when I brought the check, tipped 10% who’s husband claimed he had forgotten something at our table and ran back to give me a very sheepish apology and a $20. It was a LOT of money for me at the time.

        I remember how kind he was, and also thinking “don’t apologize to me! You’re the one who has to be married to her.” She wasn’t much nicer to him than she was to me.

        1. Morgana*

          “don’t apologize to me! You’re the one who has to be married to her.”
          I thought this all the time as a server and other customer service jobs. I have to deal with this jerk for about an hour, you have to go home with them.

        2. Another Academic Librarian too*

          I do this. I once went back to a restaurant later in the day to apologize and hand over a twenty.

          1. Grumpy Elder Millennial*

            I once went back to a restaurant because my date left a terrible tip. Wasn’t sure in the moment how to address the situation, so I just doubled back later on.

        3. RagingADHD*

          I used to do this every time I went out with my dad and stepmother. Then at some point he caught me doing it and started tipping better and apparently said something to her, because it got a lot better. But not everyone will modify their behavior in response to (appropriate) shame.

          1. JustaTech*

            I used to hide extra tips under my plate when going out with my grandmother, not because she was demanding but because she just couldn’t get around the idea that a tip needed to be more than 10% in 2003.

      2. Le Sigh*

        I once had a customer who wasn’t easy to deal with but okay-ish until the end. She absolutely flipped out over …. honestly I still don’t know. Every person in the vicinity could hear her (customers kept asking me about it later). It had the vibe of someone who wasn’t entirely well. Or maybe she was just a really angry, abusive person.

        In the aftermath, her daughter — who looked about 15, 16, 17? — came back to apologize to us, looking so embarrassed and sad, like this had happened a lot. I was young myself, didn’t really know what to say other than to assure her that we’re okay, not to worry, it’s not her doing, but thanked her nonetheless. I still think about that kid many years later.

      3. Ally McBeal*

        My mother is rude and a bad tipper (and gets offended when she sees me, a former server, adding cash to the table), so I’ve become very good at hiding cash under plates. I’d never thought about slipping it to the server directly while I’m en route to/from the bathroom but I’ll do that next time I have to eat out with her.

        1. actual cat herder*

          ooooh hiding under plates is a good one!! my uncle & father aren’t rude, but horrible tippers and i’m always backtracking

      4. Up the Down Staircase*

        I used to have to do this when we went out to eat with my now-ex-MIL. So fucking embarrassing to have to deal with someone like that.

      5. MigraineMonth*

        I once left a note and tip on someone else’s table after the couple sitting there made a huge scene over… an unsatisfactory hamburger or something? …for twenty minutes. The whole interaction felt slimy, like they’d pulled exactly this stunt a dozen times before and knew the server couldn’t push back on any of their complaints.

    2. ferrina*

      I think this applies to the vendor/client that is taking them to the restaurant, as well. OP shouldn’t avoid these meals- if OP can gracefully handle their boss’s behavior, it will make the vendors more willing to work with OP (and maybe find ways around the boss).

      For example-
      When someone calls to ask OP about what restaurant the boss may like, diplomatically say “She seems to like all restaurants equally. She has very particular tastes, and I don’t know if she’s yet found a restaurant that has met her personal standards. She does like trying new restaurants, so what about X?”
      Anyone that knows your boss will know what you are saying- your boss will act boorish no matter which restaurant they choose.

    3. MissDisplaced*

      Unfortunately, unless this person gets checked by her boss and/or a Huge Important Client and told to knock it off. she’s going to keep doing it.

      I personally don’t think it is the place of OP to be the one.

  7. Audrey*

    It’s very possible that the people who are out to dinner with you were servers at one time too.

    1. NotRealAnonForThis*

      …and taking notes.

      I absolutely do. It was one more tick in the “nope” category at OldJob…the new guy in charge was an absolute impossible ass in situations like this too.

    2. VanP*

      This behavior seems to be a “nouveau riche” thing. It is the result of people trying to deny their plebeian roots. They forget that the people they are trying to impress by being rude to those they consider below their current exalted status may have similar roots, and remember all too well having customers like them.

      1. Some Words*

        It’s not that fancy. A relative of mine is pretty poor but boy does she like to lord it over anyone she perceives as any sort of service provider; from doctors to waitstaff. Getting meals comped by complaining was a favorite hobby.

      2. Petty Betty*

        Agreed. Every rude diner I’ve ever met has never been from a multi-generational inherited wealth situation.

      3. Observer*

        This behavior seems to be a “nouveau riche” thing

        Nah. I don’t think it’s that deep.

        And both “old money” and “nouveau riche” can be equally bratty or nice.

        1. Quill*

          It’s never about how old your money is, it’s always about whether you feel powerful because you’re driving someone else, who is not paid enough to put up with your crap, up the wall.

    3. tangerineRose*

      I worked in fast food, not in a restaurant, but I’d still be horrified by this woman.

      Also, what person with any common sense is rude to people who handle their food?

      Also, never order the same dish that she has – you don’t want your food and hers to get mixed up. (I don’t have any stories about people messing with food, but I’d be surprised if that’s never, ever happened to her.)

    4. AnalogMayhem*

      Few clients would say this out loud, but I bet that this company has lost clients precisely because they had to dine with this awful C-suite individual. And rightly so.

      1. B*

        That’s what I kept thinking! Some of these are meals with *clients?!* I don’t know what this C-suite person is bringing to the table, but if I were a client she would have to be pretty spectacular for me to overlook this kind of performance.

  8. Chanel No. π*

    “…asks the bartender to make her something off-menu (usually with lots of instructions and ingredients). Without fail, she does not like that custom drink and sends it back in a way that implies that the server didn’t take all of her instructions or the bartender is bad at his job.”

    Ugh. This is one reason among several why I don’t love “When Harry Met Sally”. At the end, when Harry says, “I love that it takes you an hour and a half to order a sandwich,” — really? If I’d been him, that first night when Sally is ordering pie, I would have been disinclined to pursue a friendship with someone who treats a waitron like a personal assistant.

    And what especially kills me is that Nora Ephron was like that for real! Making everything unnecessarily complicated, like, “I want the spinach on the left quadrant and the watercress on the right quadrant.” [A quadrant is one of *four* segments; did she mean upper left or lower left?] And people thought that was *so* cool; she was *so* literary and precious. Ugh again. I just hope she tipped well to make up for it.

    Anyway, your boss is a putz. Sorry you have to deal with that.

    1. Dust Bunny*

      No, Hell, no. This would be a first and last date/meal meetup for me. My mother has some elements of this and even that can be hair-tearing: Just eat your omelet, Mom! Stop trying to give them an exact mushroom count.

    2. Snarkus Aurelius*

      I also hated that movie and Nora Ephron for exactly that reason. It’s not cute. It’s not endearing. It’s annoying and pretentious. You aren’t special! I wouldn’t have eaten out with Sally a second time!

      People like this boss and Ephron (yes, I know she’s dead) need to be a server on Mother’s Day or Easter or Thanksgiving for minimum wage so they can see what it’s like to be on the other end and get no tip. And work the patio to make shit *just* that much more challenging!

      P.S. a former friend of mine was very dedicated to WW. She would cross examine the servers over the calorie counts for *individual* ingredients like they were her own nutritionist. Then she would get mad if they estimated or straight out didn’t know. I tolerated her and tipped extra until she started insisting all sauces, dressings, croutons, vegetables, fruits, condiments, whipped cream, and butter be on the side *and* she brought measuring cups and spoons in a Ziploc bag to measure everything she ate.

            1. Ellie*

              Sally almost certainly suffers from this, yes, but at least she’s polite, specific, and tips well. Better than OP on all counts!

              1. tangerineRose*

                I don’t remember exactly, but I thought Sally’s requests were, while very specific, things that might make a difference.

    3. You Can't Pronounce It Anyway*

      When my husband and I were first dating, he said he paid attention to how I treated wait staff. I did the same for him actually! It can be very telling of a person!

      1. MigraineMonth*

        Waitstaff, cashiers, janitors, delivery people… anyone you could get away with being rude to. That’s the difference between someone with manners and someone who knows how to suck up.

    4. Finn*

      I also hate that movie! I didn’t see it until I was an adult, so maybe there’s some nostalgia factor for my peers, but I felt like he just negged her the whole time and I didn’t want them to end up together.

      1. Goldenrod*

        Finn – YES! I can only speak for myself, but what I can tell you is that I am Gen X and went to see it in the theater when it first came out.

        My friend and I walked out halfway through because we hated the characters so much. And we found it very sexist and annoying and off-putting. I don’t hear about too many other people hating that movie, but I truly hated it…you are not alone!! ;D

        1. Chauncy Gardener*

          I DESPISE that movie for all the reasons above. All the characters were totally annoying and jerky and just yuck

    5. Lurker*

      I’m an admittedly picky eater and while I’d like to be like Sally so I can eat dishes with only things I like in them, I also don’t want to be a gigantic pain in the ass. So I normally try to pick something where I like 99% of the ingredients and just ask them to leave out the 1% I don’t. Like I’ll order a salad but ask to hold onions; or burrito with no sour cream. I never ask to remove X and then add Y. I’m also nervous that if I’m too difficult they’ll spit in my food, or something.

      1. ferrina*

        This. I can be picky, but I try to be a low-impact picky. When possible, pick a dish that doesn’t need changes. If nothing on the drinks list looks good, stick with water. Keep the changes minimal and easy to create. Be kind and appreciate your waitstaff- this is where they show how skilled and professional they are, and they should be appreciated for that (both in terms of attitude and tipping).

        1. Grumpy Elder Millennial*

          Same here. There are some pretty common ingredients that I hate. The sliver lining is that it usually cuts down the available options on a menu and deciding what to eat is easier. There are usually a couple things on the menu that work for me as-is, or with just dropping something.

          Occasionally, I’ll ask if a dish is available without X and it turns out it isn’t because of things being pre-mixed or the ingredient being a key part of the cooking process such that dropping it will likely result in a terrible meal. So I pick something else. It’s not hard to be nice.

          1. tangerineRose*

            Yep, me too. I’m another picky eater. It’s not hard to be nice and to remember that some stuff is pre-prepared and can’t be changed.

      2. Orv*

        I’m not a picky eater in general, but there are ingredients that are dealbreakers — in particular, cilantro. There are some cuisines where it’s literally in every dish. I usually try to select something where it’ll be easy to leave out (which is to say, one where it isn’t prepared well ahead of time.)

        1. Grumpy Elder Millennial*

          Yeah, there are some cuisines that I generally wouldn’t go to a restaurant for, since I’m going to have a hard time. No sense in putting any of us through the experience.

          1. Orv*

            As a cilantro hater I generally avoid Vietnamese and Indian food for that reason. However, it’s also near-ubiquitous in Mexican food and it’s almost impossible to exist in SoCal and entirely avoid Mexican. Fortunately it’s usually a garnish and easy to leave out.

      3. Nah*

        Oof, that’s an entire mood right there. I spent the last five years at this lovely hibachi restaurant under the worry of looking like a five year old not eating their vegetables, or looking like a *different* five year old choking down the zucchini on my plate because from my prior experience (to be fair, in much cheaper, often mall-food style places) most other restaurants had the vegetables pre-mixed.

        I’d already been expected to strain still-boiling cheese sauce off the Panera noodles *with my bare hands* in a previous job, I didn’t want to make the chef pick out each and every little piece of squash for my meal.

        I mentioned this problem to a friend, who, very logically, responded “well, have you ever actually asked?” and the mixed relief and embarrassment that it just took a three second question to the server and was actually a relatively common request was… certainly something. Glad I got that reality check (and that I can actually finish my plate now!), but thinking back at it… hoo boy.

      4. Freya*

        My pub trivia team knows exactly what I’ll want to order every week – one particular salad minus cheese minus onions light on the sauce. They always confirm that that’s what I want, but it’s usually what I want because I know it’s safe and I just don’t want to waste the brainpower I’ll need for the trivia on trying to figure out something else that my tummy will like. We go there every week, and try to be kind to the staff, because they do good work and they work hard, and they take care of us.

    6. Another Academic Librarian too*

      I am that person cilantro disagrees with. I don’t order things that state that cilantro is an ingredient but I have sent things back when its generously sprinkled over the dish.

      Good news on the Nora Ephron front. She was a generous tipper and encouraged all others to be one too. She wrote (I paraphrase) that extra five dollars is nothing to you (in the context of a meal or cab ride) but is everything to the server or driver or hairdresser)

      And on the annoying front, I did actually have a meal with an acquaintance who took a half hour to order and sent the server back to the kitchen to check on ingredients twice! During the ordeal all I could think was “you just shouldn’t eat out” and I will never eat out with you again.

      1. Observer*

        During the ordeal all I could think was “you just shouldn’t eat out”


        My husband and I both have some genuine diet issues that really limit what we can eat (and some of the ingredients I can’t touch are a pain to deal with.) It’s one of the reasons we rarely eat out and are fairly picky about where we do when we do go out.

        1. Jay (no, the other one)*

          My husband has an unusual dairy allergy that (thankfully) is not life-threatening. He can eat butter, but no other dairy (yes, this is a thing because it’s a milk protein allergy and yes, his doctor agrees it’s a thing). He hates having to be that person. It makes travel exhausting. We’ve learned that it’s much easier to eat in higher-end fine-dining restaurants because the servers know what’s in the food and the chefs are more likely to be able to adjust. Worth the money, to us.

          1. Paint N Drip*

            I have the same allergy and people just don’t understand (it isn’t lactose intolerance!!!)
            When you have food issues, I agree that going to a place that MAKES all the things is so much easier and the extra cost is so worth it

      2. I Have RBF*

        During the ordeal all I could think was “you just shouldn’t eat out” and I will never eat out with you again.

        Just because they wanted to know what was in their food so they wouldn’t get sick?

        I sincerely hope that, as you get older, that you never end up dealing with food allergies/intolerances. Because when I was in my 20s, I could eat damn near anything. Now in my 60s, and I can’t eat really common stuff like soybean oil and cilantro, and have to take a lot of lactaid to eat milk products.

        IMO, there’s nothing wrong with needing to know what is in your food. I have friends who get anaphylactic reactions to things like mushrooms or shellfish. If it takes them a half hour to order so they don’t die? I’m fine with that.

        1. al*

          …? You completely invented the acquaintance’s motives. Like, did Another Academic give more detailed context in another comment, or is “[food] will make acquaintance sick” entirely your own assumption?

          1. I Have RBF*

            IME, the reason that most people want to know what’s in their food is so it doesn’t make them sick. I do not consider that an unreasonable assumption to make.

            1. al*

              And it’s still an assumption, which for some reason you asserted over Another Academic’s personal experience. This is a single person’s anecdote. “The reason most people” doesn’t apply, the same as one person’s anecdotal experience can’t be used to extrapolate anything meaningful about “most people.” Another Academic omitted some information; that doesn’t mean any assumptions you make are correct.

        2. Jill Swinburne*

          If the issue is that severe, you tell the server before you order, so they can convey that to the kitchen. They don’t get paid enough to mind read.

          1. I Have RBF*

            Yes, that’s why they complained that it “took them half an hour to order”. If you know that X, Y or Z will make you anything from mildly nauseous on up, it can take a while to ask the server to check what is in the menu items.

            Yes, I prefer to look it up on the company’s website, but the ingredients are often not fully listed.

            No one mentioned asking a server to “mind read”.

        3. Observer*

          <i.Just because they wanted to know what was in their food so they wouldn’t get sick?

          In general, there does come a point where you may have to decide not to eat out.

          As I said in my other post, there are a lot of things that I cannot eat. And it’s one of the reasons I eat out very little and when I do eat out, I have a *very* few places that I’ll go and a very few items on the menu that I can touch.

          Do I like that? No. Is it reality? Yes. Do I blame the restaurants for this? Absolutely not. Do I understand people who are made uncomfortable by this kind of thing? Totally.

    7. bookmark*

      If you want a real-life and very sweet counterpoint to all this, check out some of the articles about the first date between Ohio Senator Sherrod Brown and his wife, columnist Connie Schultz. Connie had written a column several years prior to their meeting quoting the relationship advice her mother had given her as a teenager– “Don’t marry him until you see how he treats the waitress.” Sherrod had read the column to his family at the time, and before their first date, made a point to have already met all the servers and could introduce Connie to each of them by name.

    8. lilsheba*

      There is no need to be dissing Nora Ephron. She was a brilliant writer and I love When Harry Met Sally, every single moment of it. Being particular about how you want your food is not bad thing. Not ONCE do we ever see her send it back or berating someone over food. So your point is not a good match.

    9. just some guy*

      If you cut it diagonally, the four quadrants can be left, right, up, down, I guess?

      But still a bit “none pizza with left beef” for my tastes.

  9. Ashley*

    Are there opportunities for another manager or your boss’s boss to go to lunch and witness this stuff first hand? I am not sure I would feel comfortable commenting given the amount of egregious behavior, but it would be nice for someone in more of a position of power to witness this.
    Is there any chance drinking during the work day is not allowed and you could at least stop that part?
    Your hosts are right to start skipping the perk of offering a free meal. If they do want an alternative maybe suggest they have food delivered to the office.

    1. Snarkus Aurelius*

      I bet if the big boss attended these events, this boss would clean up her act. She knows enough not to visit a second time so she has some self-awareness.

      And if that does the trick, then yay? (Although if I had to babysit someone’s table manners, I’d be pissed.)

    2. Damn it, Hardison!*

      This was what I was thinking as well. It would be so telling if she did not behave the same with her manager in attendance.

    3. Petty Betty*

      I was thinking about the grandboss hearing about these antics and then witnessing them too. It would be wonderful to see the grandboss doing an “undercover boss” type situation where they… mystery dine? in the same restaurant and see firsthand how she acts at business dinners.

  10. HonorBox*

    I think three things here:

    1. Firmly agree that your boss is an ass. She is one of the customers restaurant staff (from waitstaff to chefs) hate.
    2. It is obvious that those you’re dining with are picking up on it. For those who aren’t saying something about skipping dinner, they probably would like to.
    3. Totally agree with the advice about going out of your way to be thankful and offer praise, and to find the server and offer an apology.

    I’m not sure there’s much actionable yet. Your boss may not be open to you proactively offering feedback. But there may be an opportunity in the future that opens the door. If she wonders why a dinner invite isn’t coming from those you regularly get the offer from, maybe point out that she seems displeased throughout the dinner and that may have turned them off to even offering again.

    1. Reality.Bites*

      I can’t imagine someone so rude and inconsiderate of others being open to feedback. I’d be afraid to try it in OP’s position.

    2. Pastor Petty Labelle*

      I would not raise it even if asked. A little white lie, oh they pushed for time and can’t take the time for a meal would be good here.

      Because I guarantee you that if OP raises her behavior with boss, not only will boss justify her behavior, she will take it out on OP that her behavior might be a problem. OP has to work with this person all the time, not just at the meals.

      1. Smithy*

        I’m in this camp.

        Obviously this person’s behavior with wait staff is rude and negatively effects the larger community – so it would be great if she changed for society. But in a work context, this strikes me as being similar to having a C-Suite boss who has really off table manners. Talking with their mouth full, belching at the table, etc.

        I’d just aim to schedule meetings not around dining as much as possible, or aim for the dining in question to be as minimal as possible (i.e. meeting for coffee or drinks).

        1. Observer*

          But in a work context, this strikes me as being similar to having a C-Suite boss who has really off table manners. Talking with their mouth full, belching at the table, etc.

          Disagree. The behaviors you describe are rude and pretty disgusting. But they are ultimately harmless. What the LW’s boss is doing *is* harmful – and I’m pretty sure that she knows it. And that to her “it’s a feature, not a bug.”

          1. Smithy*

            In no way I disagree. However, I think both behaviors aren’t helpful and potentially hurtful in a business context. Just in different ways.

            But in both cases, I really don’t see a more junior colleague having a lot of opportunities to change the behavior.

  11. Three Flowers*

    The one silver lining I see here is that clearly your clients recognize that your boss is an ass but *you* are competent, strategic, and a decent human, and have tolerance for adversity. We don’t know your industry, but could you leverage that and go work for one of them?

    1. Richard Hershberger*

      Yup. That they are trying to use the LW to make an end run around this person shows that they can distinguish between the two.

    2. tree frog*

      There could also be an opportunity to use these indirect complaints as leverage with your boss. Every time someone asks you to pick a restaurant, could you relay that to your boss and mention that they seemed upset that she didn’t like the place they picked last time? If she cares about her job, regular feedback that she is ticking off clients might make some kind of impression with her. Although it’s hard to imagine that someone who acts like this isn’t insufferable in other ways.

    3. Lyra Belacqua*

      Yep, this. This sounds like it could be my city and industry, which is one that requires the ability to deal with difficult people, and they’re certainly noticing that you’ve managed to work for your boss for this long. If they’re emailing you to find other arrangements, they absolutely get it.

  12. Justin*

    I feel like this woman watches too much I Think You Should Leave and internalized the behavior.

    1. Not Tom, Just Petty*

      I certainly agree the boss thinks she is the main character in a show about food and her companions are there as props.

    2. Toast*

      The steak was missing “something” and by “something” she means a full glass of water poured over it

  13. ragazza*

    Is there someone on her level or higher who you could (tactfully) ask to speak to her about this? I think hammering home the effect this might have on business opportunities might help. But it would be better coming from someone who isn’t a direct report if possible.

    1. Harper*

      Yes! OP, maybe confide in a higher up and ask them to invite themselves to the next dinner “for the purpose of getting to know the vendor better” (or whatever). Then the higher up can call Boss on her behavior without OP appearing to be involved. This would, of course, backfire if Boss intentionally dialed back her assery in front of the higher up.

      1. Lenora Rose*

        Would it? The vendors would be happier, the boss better behaved… the only way it would backfire is if the boss’s boss then doesn’t believe what has happened elsewhere. Which does mean you’d need the vendors to be people who’ve gone to a restaurant with her before and can attest that this good behaviour isn’t normal.

    2. HonorBox*

      Interesting thought. And reporting to someone higher up that clients are declining to have meetings that seem relatively regular might show that higher up that there could be impact on the business… which makes it more than just “we don’t like dining with someone who is intolerable to eat with.”

    3. learnedthehardway*

      Agreeing. The OP shouldn’t be the one delivering this constructive criticism. A manager who behaves this way with restaurant staff is highly unlikely to take feedback from an “underling”.

      The clients are being VERY diplomatic about suggesting NOT going to a restaurant, rather than stating that the manager’s behaviour was embarrassing. But they are CLEARLY unhappy about it.

    4. holdonloosely*

      If OP feels comfortable enough with one of the clients who’s hinted at their discomfort, one solution would be to diplomatically convey to the client that they might mention something to a higher-up. Then it becomes a business problem (which it is!) and OP’s grandboss can let their manager know she needs to knock it off. (Which, frankly, would be doing her a service, even if she doesn’t see it that way. The behavior is obnoxious as hell.)

      1. Trina*

        I was surprised that Alison did not comment on the fact that this behavior seems to be damaging relationships with clients and vendors! That aspect of it at least I would think could be brought up to a grandboss in the usual “how would you like me to handle this” tactic of seeking help in a problem-solving manner.

      2. Grumpy Elder Millennial*

        100%. The clients absolutely have standing to comment on this to someone above the LW’s boss.

    5. I should really pick a name*

      If they’re feeling passive aggressive, invite the higher up to a meal with their boss. Let them see it firsthand

      1. Ineffable Bastard*

        The dream would be having the higher-up undercover in a different table. I doubt that “foodie” would be so blatantly rude in front of her boss.

    6. Grumpy Elder Millennial*

      Or even to raise it as an issue that you’d like their guidance on how to deal with, if there’s some fear about “going over her head” or whatever.

      1. Grumpy Elder Millennial*

        And it’s not that *the LW* thinks her behaviour is awful, it’s that *clients* have complained.

  14. Dust Bunny*

    AAAUGH what a nightmare. I effectively ended a friendship with someone like this. She was another self-described “foodie” and was picky beyond belief. She liked to go out to eat with me because I’m basically a raccoon and would be game for whatever restaurant she wanted to try. Except her behavior was so embarrassing I finally had to tell her I didn’t think we were meal-compatible. She didn’t think I was worth spending time with if I couldn’t be an audience, so we haven’t seen each other since. No loss. But my job didn’t depend on humoring her, either.

    1. 3-Foot Tall Inflatable Rainbow Unicorn*

      Thing is… the boss’ job depends on humoring clients and yet the boss behaves like this in front of clients! That’s the part that boggles me the most – not that boss has delusions, but that boss wants to be the Main Character to the people who are the reason she’s in business!

          1. Plate of Wings*

            Yep, I’ve seen people part ways with vendors/clients for so much less. How are you going to trust the judgement of someone who treats someone like that at THEIR workplace (the restaurant)?

            1. tangerineRose*

              I’d be wondering how this boss treated her subordinates and not want to deal with someone like that.

      1. Antilles*

        Seriously. Maybe it’s just me, but this sort of behavior would make me wonder about your competitors. Both because it’s a sign of the kind of person you are and also because I’d be thinking “wait, you’re supposed to be on your best behavior in front of clients”.

      2. Dust Bunny*

        I think there is a subset of people who believe that this makes them look sophisticated or like they have high standards.

        I mean, I appreciate good food and there are definitely categories of food I like better than others, but in real life, as long as it’s not trying to escape or covered in mayonnaise, I’ll probably eat it. And even mayonnaise can be scraped off.

      1. ThursdaysGeek*

        Server: you wouldn’t believe the table I got! One person was so picky, had to know all the ingredients, kept sending things back, was always calling me to the table for something else. The other one? Only words were ordering the special plus a bowl of cold water. No, not a cup, a bowl.

    2. Elle*

      I honestly haven’t met someone who enthusiastically calls themself a foodie and ISNT ridiculous to the point of being difficult to eat out with.

    3. toolegittoresign*

      It baffles me when people call themselves “foodies” but then never seem to like ANY restaurant. It feels like people have commandeered the term to mean “I have impossibly high standards and odd tastes.” I would consider myself a “foodie” but I am okay with everything from chicken nuggets to squid ink pasta.

      1. starsaphire*

        Yes – in my experience, foodies want to try EVERYthing and taste everything. And try to figure out what’s in the dish so they can make it at home!

        Foodies say things like, “Oh, I never thought to use oregano quite that way,” or “Yum, how did they get this texture?” or “Yes, that is a fish that can handle a red wine.” Foodies order all the desserts and everyone takes a bite of everything. (Like the French Laundry episode of A Cooks Tour, where everyone takes a bite and passes the dish to the left, so they can all try every dish.)

        Foodies do not do what the boss in this post is doing, and we — er, “they” — probably resent being grouped with her.

        1. toolegittoresign*

          and also… if I don’t like something, I chalk it up to not being for me. I have NEVER sent anything back to the kitchen unless it was a food safety issue and was always very polite about it.

          1. Dust Bunny*

            I have sent food back twice that I can remember: Once was gumbo that was definitely **burnt**, and the other was raw chicken. Every other time I just go, “Well, I know not to order that again,” and move on.

          2. I Have RBF*

            The only times I have ever sent food back was when they left something off, improperly cooked it, or they added something that I couldn’t eat. Maybe one in a hundred or more meals: Raw chicken, surprise marshmallows or whipped cream, zucchini when I asked for peas, burnt anything that was not meant to be charred, etc.

            My spouse worked for restaurants. She has stories…

          3. Freya*

            The first time I sent food back (one of the very few times I have sent food back!) I was a teenager, and the chicken tasted like fish. My parents coached me through the process of being nice about it and clearly explaining the problem to the waitstaff so that they could let the chef know about it and the chef could fix whatever caused it in the kitchen (the chicken could have been cut up on a fishy chopping board, or the shipment of chicken could have been off, and both of those need different process changes). The restaurant was really nice and supportive of my first foray into this unknown realm – I think they could tell that I had never done it before and really didn’t want to put anyone out.

          4. londonedit*

            The only time I’ve ever sent something back was when it was still frozen in the middle (it was an apple crumble, and it was a pub, so I let them off not having made it all from scratch themselves). Mind you I’m British, and sending things back in a restaurant is seen as being even more rude and boorish than it would be in the US. What we do is smile, say ‘Yes, thank you, everything was fine’, pay the bill and then once we’re out of the restaurant say ‘Well, we won’t be going there again’.

            I have absolutely been out with people who have been terrible about food (or wine) and it’s just the most cringeworthy experience. I went through a particularly bad run of it in my late twenties/early thirties, mainly with friends’ new boyfriends who were desperately trying to show off about how grown-up and knowledgeable they were. The sort who’d demand to see the wine list and loudly proclaim that there wasn’t anything on there that they’d usually drink, but ugh I suppose we can deal with a Viognier if we absolutely have to. And then they’d make a big show of sniffing and tasting the wine. Absolute pains in the arse (and thankfully usually didn’t last too long as boyfriends!) If the boss is still acting like a silly boy who’s trying to impress his girlfriend’s mates then she’s got a serious problem and she isn’t a ‘foodie’, she’s just a bit of a dick.

        2. Angstrom*

          I fondly remember listening to Jane and Michael Stern doing their “Roadfood” reviews. They would be genuinely delighted by a good grilled cheese sandwich or biscuits and gravy.

      2. le teacher*

        Sort of like Anthony Bourdain! He would eat anything from fast food to michelin starred places. He saw the delight in it all. That to me is definitely a real foodie.

    4. Shopping is my cardio*

      I also stopped going out to eat with a friend couple for the same reason. The husband would inspect every dish and send everything back: I ordered the 8oz steak, this looks like 7oz. Everything was at fault and he would scoff and roll his eyes when the food came out, like.. ugh how dare you serve this to ME.
      I went out with them a couple of times and said never again, it is not worth my aggravation and second hand embarrassment. Also I have been a server and I DO hope that someone spat on his food.

    5. Hroethvitnir*

      Wow. Not surprising outcome but good god.

      I have a good friend who would *never* call himself a foodie due to this association – but is obsessed with trying new things, has an enormous palate, and piqued my interest in such things.

      This means we have gone to very expensive restaurants that are more of an experience than anything, and now I too am addicted to regularly trying new flavours and combinations (as someone whose day to day diet is the opposite of this).

      Anyway, it’s sad to me, because I now very much appreciate Weird Food Experiences, yet pretentious weirdos with no joy ruin the idea for most people!

  15. new post, new name*

    Why, oh why, do so many people think that being rude, obnoxious, and demanding is some kind of power flex? When it really just makes you look like – as Allison said – an ass. It’s a wonder that OP’s boss manages to retain vendors and clients at all.

    1. tangerineRose*

      When I worked in fast food, we got people who made it very clear that they thought they were above anyone who worked there. It was pretty clearly a problem with them.

  16. The Gnome*

    This is gonna end up being that boss’s legacy, I just know it.

    My great-uncle Harry did a ton of cool stuff during his lifetime, but he’s been gone 37 years now and all the family talks about when they talk about him is how shitty he was to the wait staff. This boss is gonna go the same way at thia rate.

    1. Plate of Wings*

      This is so true! It’s a piece of information about character that conveys so much, it overshadows someone’s other interpersonal interactions for a reason!

    2. tangerineRose*

      Dave Barry said something like ‘A person who is nice to you, but rude to the waiter, is not a nice person.’

      He’s right.

  17. Juicebox Hero*

    May every restroom stall she uses be out of toilet paper, or better yet, only have that one last square stuck to the roll that you can’t pull off without tearing it to bits.

    May she never go barefoot without stepping on Legos.

    May both sides of her pillows ever be warm and moist.

    May there be a shrieking, kicking toddler behind her on every flight.

    May she be afflicted with chigger bites every summer on her arms AND legs.

    It’s really not fair that you can’t force people like this to work as a server/ cashier/ whatever service position has to suffer in their presence for at least a month to teach them a lesson.

    1. MsM*

      Wasn’t there some case where a judge sentenced a person who threw a tantrum (and I think their food) at a server to go work at the establishment for a month? I think it was a Chipotle or something?

      1. Lady_Lessa*

        Yes, your memory is accurate down to the restaurant. I just wish I knew of a follow up, after the person did the job. Many commenters wanted her away from dishing up food, and just cleaning the restrooms.

      2. Bananapants Modiste*

        Emily Russell was working at an Ohio Chipotle when an angry customer, Rosemary Hayne, violently hurled a hot bowl of food in her face — an attack that was caught on video. Now, Hayne, who was found guilty last week of assault, has agreed to work in a fast-food restaurant to avoid jail time.
        “Do you want to walk in [Russell’s] shoes for two months and learn how people should treat people, or do you want to do your jail time?” Judge Timothy Gilligan asked Hayne at her sentencing.

      3. Orv*

        I know the judge thought that was poetic justice, but all I could think of were the innocent coworkers who were sentenced to work with someone who was there as a punishment. Imagine how demoralizing that would be. “Your job is so bad we make people do it if they commit a crime.”

    2. br_612*

      May ever coffee she drinks be tepid, every beer or soda hot and flat, and every sip of water be unsettlingly warm, like leaving a bottle in a car in Texas in August.

    3. Emotional support capybara (he/him)*

      May her children receive percussion instruments for every birthday and gift-giving holiday until they move out.

      1. Grizabella the Glamour Cat*

        O/T, but I love your handle!

        A capybara would be an awesome emotional support animal, imo!

    4. Katara's side braids*

      May she always think she sees an empty parking space in a full lot, but it’s actually a small car/motorcycle. May she already be running late when this happens.

    5. The Gnome*

      In the same vein as the chigger bites, may she only be able to visit Maine during black fly season.

    6. Marzipan Shepherdess*

      Love all of your “prayers” except the last: “May she be afflicted with chigger bites every summer on her arms AND legs.”

      What have you got against the poor chiggers??

      1. Juicebox Hero*

        That’s true, even chiggers deserve better.

        May she be bitten all over by ticks who spit her blood back out and complain about it being made wrong and lacking hemoglobin!

    7. Aww, coffee, no*

      May her pantyhose get a run just as she’s leaving the house.
      May her supermarket trolley always squeak and pull to the left.

    8. Aww, coffee, no*

      Oh, and of course: may the work coffee pot always have just a smidgen ‘no, I didn’t finish the pot so I don’t need to start a new one, said the previous user’ left in the bottom when she gets to it.

    9. Observer*

      It’s really not fair that you can’t force people like this to work as a server/ cashier/ whatever service position has to suffer in their presence for at least a month to teach them a lesson.

      I really don’t think that this is the issue. I know that it comes up a lot, but it’s never made any sense. *Toddlers* generally behave better than this woman. My parents were never servers, but not only would they NEVER be rude to a server, they would probably have disowned any of their children who mistreated wait staff. Even some family members who are a bit snobby that way and kind of look down on “the help” would never do stuff like this, nor yell at people, make a scene in public, etc.

      On the other hand, some of the people I know who are the most likely to act out in public have backgrounds (not necessarily in food service, but still) where you would think they should know better. I’ve seen many comments here over the years as well about people who are former servers who think that this actually entitles them to be rude to wait staff because “it’s their turn”.

    10. Three Flowers*

      I’m printing this thread for future use—like, say, a ritual directed at my grandbosses once I get a new job.

  18. CityMouse*

    I understand you 100% but I don’t think given the nature of the relationship, you can do anything. Realistically boss has to know she’s rude, she just doesn’t care.

    I would just grit your teeth and go, and maybe try to sit away from her. Don’t let her poor behavior keep you from networking. As someone who used to work food service. I wouldn’t hold it against someone at a business dinner if their colleague was a jerk.

    1. gmg22*

      “Realistically boss has to know she’s rude, she just doesn’t care.”

      I suspect that most people who act like this DON’T actually have enough self-awareness to know they are being rude. In other words, my bet is if the LW actually tried to bring this up with boss, what she’d hear back is that boss thinks acting this way is fine because she’s the customer, and it’s the restaurant’s fault for not being up to her standards.

      It’s also hard to imagine this extreme behavior not spilling over into other areas of this woman’s life, so I am wondering if she’s ridiculously picky/impossible to please about certain things in the office, too.

  19. Mytummyhurtsbutimbeingbraveaboutit*

    Perhaps there’s a way to sell this in business terms? Something similar to “hey, I’ve noticed a pattern where X was really excited to sign a contract with us until we dined with them. Perhaps we can try another way to network with them?”

    But I’m not hopeful. As Alison said, if this person was capable of that kind of introspection , they wouldn’t have this behavior in the first place

    1. Plate of Wings*

      This is a great idea if the business contact relationship has those kinds of stakes. I love this wording.

  20. wondermint*

    Ordering a cocktail and appetizer while everyone orders coffee and dessert. She has zero self awareness. This is a business meeting!

    1. GreenShoes*

      lol… maybe it’s some time of weird power move that she got from one of those budget hotel seminars

      Cheesy Motivational Speaker: The next time you are out with people. Make a power move… show them you scoff at convention… you’re not afraid to break the rules! While they are all safe and boring in their flan and chocolate mousse you show them who they are dealing with by ordering a shrimp cocktail. They’ll know who they’re messing with with that one simple move.

    2. 1-800-BrownCow*

      My oldest son (16) will order soup for dessert. He takes after me and does not have much of a sweet tooth, lol. Although I just don’t eat anything for dessert, my meal was already enough. Regardless, it’s just soup. And usually we’re eating at a diner (cheap food, family of 5, no fancy stuff for us), so no work or cooking involved. Just dishing it out of the pot of soup that’s been in the warmer all day long.

      Haha, I’m now envisioning him at a business dinner meeting one day, ordering soup when everyone else gets’ dessert and confusing everyone at the table with him. ROFLMAO!!!

      1. Polyhymnia O’Keefe*

        My husband’s family as a rule doesn’t like ending the meal with sweets — which, for normal people, is why coffee usually goes with dessert, or dessert might be a cheese plate. So there’s something to cut the sweet. But in his family, that manifests as eating one more piece of turkey after dessert, eating dill pickles after dessert, or (when eating out) doing everything you can to hide the last fries on the table so that the server doesn’t take them away, so there’s something salty to eat after dessert.

        Or, my husband’s favourite trick, ordering dessert as an appetizer. Entrees usually travel better than desserts anyway, so if you eat dessert first and then only eat part of the meal, it’s easier to take the meal home than the dessert.

        We were chaperoning a junior high out-of-town trip a few years ago, and he did that at one of our “free” dinners out, where the group split up and ended up at a bunch of different restaurants. You could just see the kids’ wheels spinning as they realized that this was a thing you could do!

        1. 1-800-BrownCow*

          This reminded me of the time we went to a chain restaurant for dinner where several of the meals come with a “free” Sundae for dessert. While ordering our food, our waitress told us that one of the cooks had to suddenly leave and so they were now short-staffed in the kitchen (slower time of day, so less staffed in general) and our food might take longer than usual. My husband then asked if we could get our Sundae’s first because he was really hungry. The waitress laughed and said sure, she could do that and a few minutes later she brought the Sundae’s out to our table. My husband and son were still eating their Sundae’s when another person of the waitstaff came out to deliver our food to us and then stopped short, looking confused when she saw them eating their desserts. We quickly let them know that we had requested our desserts first since the kitchen was backed up, which they said that was actually a great idea!

      2. Freya*

        One particular restaurant visit with my family, there was a prosciutto-wrapped baked fig with balsamic vinegar thingy on the starters menu. Every single person in the family ordered that dish, and between us all, it got ordered for starters, mains, AND dessert. And every single person who ordered it enjoyed it in the dish order placement of their choosing. It was REALLY good :-D

        1. 1-800-BrownCow*

          Oooo, that does sound really good! Definitely something I’d order for dessert if I was still hungry at the end of my meal.

    3. NYCRedhead*

      This struck me as the weirdest part. I love appetizers and don’t have much of a sweet tooth but it would never occur to me to do this.

      1. Some Words*

        Because it’s not gastronomically correct. If she were a foodie she’d know that. /s

  21. Caledonian Crow*

    It always boggles my mind when people feel that being hypercritical and rude (especially to people like waitstaff) makes them look superior and oh so knowledgeable. And I think that’s what your boss is doing here – she’s trying to show how sophisticated she is and how refined her palate is.

    She doesn’t realize that her behavior is having the opposite effect. She seems like a spoiled child who can’t manage her own feelings and finds fault with everything. I’m sure none of your clients are impressed by what she’s doing.

    Sadly, I don’t think you will be able to say anything to her that will persuade her to behave better. The clients or dinner hosts might be able to push back successfully, especially if their pushbacks involve consequences (i.e. losing an account).

    All you can do on your end is to model good manners and kindness and know that who she is doesn’t reflect on you as a person.

  22. Angstrom*

    There could be business consequences, too. Hosts will be thinking “If she’s that much of a PITA at a meal, what’s she going to be like to work with?”

    1. Katherine*

      Or that her priorities are very skewed and she’s paying more attention to food than business

    2. Aspiring Chicken Lady*

      I absolutely would rethink a business partnership with anyone this irritable.

  23. Overit*

    I successfully changed the behavior of a friend who found fault with everything in a restaurant every time. There is a critical caveat at the end of the story.
    When I tried talking to “Susie” about it, she told me that she did it to get a comped meal. It was a fun game for her to see how much she could get for free. I saw red. The next time we went out, when the waitress came over, I said, “Just a warning. Susie here is going to make your life hellacious so she can get a free meal.” Susie gasped, turned red and fled to the bathroom. Susie also never ever did that again.
    That tactic worked because 1. I was willing to go scorched earth and accept that Susie might never talk to me again and 2. Critical caveat: Susie’s identity and self worth were not tied to being difficult in restaurants. (If it had been, I would have stopped eating out with her because nothing I did would make her change.)
    LW — your boss’ identity and self worth ARE tied to being difficult in restaurants. Talking to her will be a scorched earth tactic for you. Unfortunately, you can do nothing about it.

      1. Overit*

        Thanks. I am a person with a very long fuse, but once it gets lit, I knew exactly how to aim it.

    1. Formerly Ella Vader*

      This is amazing.

      I agree with you that the OP’s boss is going to be a harder case because she has a different motivation for being a demanding customer.

  24. GreenShoes*

    Ok.. I can almost forgive the custom drink ordering. It’s a bar that’s kind of what they do. I lose forgiveness if she’s ordering something fussy and sending it back (I’ve ‘sent back’ a few drinks in my time… but if it’s a custom thing or if I just don’t like it and it’s not made wrong I’ll order a new drink and tell the server I’m still paying for the one I didn’t like).

    But everything else is just boorish behavior. I don’t really think there is much you can do except a well placed eye roll out of her line of sight when you are at a restaurant. Honestly if anyone tells me they are a ‘foodie’ I just assume them to be a pain in the ass from the get go. You’re likely not going to be able to affect any change here so I’d just chalk it up to “nobody’s perfect” and do your best to show appreciation to your servers.

    1. Elle*

      Ordering off the cocktail menu is fine when it’s a simple or well known cocktail (my metric is four or fewer ingredients)- a martini is fine, a mint julep is not. A Negroni should be ok, some dumb spin on a Negroni that someone saw on TikTok, probably not so much.

      1. Alton Brown's Evil Twin*

        Yes. And ordering a bizarre cocktail is fine when you’re out for fun, but not when you’re in a business meeting.

      2. Jennifer Strange*

        I think it also depends on the place. I’m not going to go to Applebee’s an expect the poor bartender to make me something like an old fashioned or a dirty martini (not that they can’t, but chances are they are only trained to make the specialty cocktails listed in the menu)

      3. Hastily Blessed Fritos*

        If it’s a fancy cocktail place and not too busy, I may ask if the bartender can make me something off-menu of their choice, with a few guidelines (nothing sweet, no vodka) but if I don’t like it that’s on me. I’ll always tip extra for this.

      4. Missa Brevis*

        I agree with your basic rule of simple or well known cocktails yes, obscure or complicated no, but … a mint julep? It’s literally just mint, sugar, and bourbon. It’s the same level of complexity as an old fashioned, which I would definitely consider safe to order off-menu.

        I suppose not everywhere is going to have mint, but it’s an incredibly common ingredient and garnish, so as long as you don’t pitch a fit if they don’t have any, I’d think it would be fine.

        1. DannyG*

          If she orders the same complex cocktail every time how about copying the recipe and instructions and printing on a card to give to the waiter? That would solve at least some of the problem. Tart it up a bit: print it on pink card stock and on the other side a title like: Ms A$$’s Special.

        2. JustaTech*

          I think the idea with a mint julep being a bit much is like when mojitos were super trendy – all that muddling is a lot of fuss and takes a while, so it’s more of an ask of the bartender than something like a dirty martini.
          But usually the advice is “don’t order this if there’s a huge crush, and if you do order it, tip more”.

      5. Reading Rainbow*

        I worked in some very high end cocktail bars at one point, it’s fine to order off-menu (even something fussy, even something you saw on TikTok) as long as the bartender is not super busy and you are nice about it.

        The reason to stick to the menu or common, simple drinks if it’s busy is because there is a lot of pre-prep done for those ahead of time that makes them faster to make. Cocktails are time consuming to make (which is a major contributor to why they are priced they way that they are and why mocktails are not a lot cheaper) and bartenders are making a tipped minimum wage in most cases, so as long as you’re being respectful and tipping well no one is going to get cranky about fixing something different.

        The big reason cocktail bartenders might be reticent to offer a recommendation or make you something you saw online and haven’t tried is that, in our experience, people don’t like new things and they generally only like very mild, sweet drinks. So it’s not that it’s difficult to make it, it’s that they are afraid they will make you something you don’t like and then you will be unhappy. That happens a lot.

    2. Hot Flash Gordon*

      We have a family friend who is terrible to go out to eat with (she’s never rude, just fussy and likes to be the center of attention…and tips well) but she is so embarrassing. She once ordered a glass of Merlot at a comedy club and sent it back because “it just didn’t taste right.” Like…it’s a comedy club lady. I’m sure their house “merlot” comes out of a weird tap labeled “Red”.

  25. Keymaster of Gozer (she/her)*

    Generally speaking people don’t change bad behaviour unless they want to. I’ve an uncle who I refuse to have anything to do with because he insists on hurling offensive slurs at retail/hospitality/transport service people. He will never stop seeing them as his servants to order around as he wishes.

    Maybe, since these are business meetings though, you might be able to put across that you’ve had feedback from other people that she’s making them incredibly uncomfortable with her behaviour (ordering waitstaff around, stiffing them on tips etc.) and could she try and be a bit more easy going and accomodating?

    I don’t hold out much hope though. These entitled types rarely change.

  26. Not Tom, Just Petty*

    OP, I understand that you cannot tell your boss that foodie is a ridiculous term and if she wishes to be a true gourmand, she should start by loving food instead of challenging it. Oh, wait, that’s my thing…your thing, can you tell her that “Jim said he didn’t want to do a meal for the meeting because she was so unhappy with the meal last time, he didn’t want to have it happen again?”
    or “Jane said that she wants me to suggest places that will meet your (abstract and arbitrary and authoritarian wants) high standards.”
    You can explain that they are concerned they will not be able to do their best presenting or whatever if the meal is a distraction.
    All true, just leaving out the part where she is choosing to be distracted by her ass-holier-than-thou foodism.

  27. Risk Factor*

    God it probably wouldn’t help, but if I was paying and she muttered about the tip being lowered, when the bill arrives I would be so tempted to very loudly, pointedly, raise it.

    Because SOD that behaviour.

    1. pally*

      If only to hear her object and then explain that “there ain’t a gratuity large enough to properly compensate anyone who has to put up with your ridiculous antics!”

      Course, then I’d be fired. Worth it.

  28. surpriseprohibition*

    I know its a norm in some industries but the idea of ordering a custom cocktail at a business lunch is flabbergasting.

    1. Lady Whistledown*

      Not sure there is much you can do about her boorish behavior without intervention from someone higher up. But one possible solution to mitigate the awkward appetizer order at the end would be to say something to the server while you’re ordering like “Boss tends to finish her meal with a cocktail and appetizer while the rest of us have coffee and dessert. When would be the best time to put that order in timing wise?”

  29. Smithy*

    If I were you – as much as possible, I’d try to steer away from full lunches/dinners whenever you have the chance to instead push for coffee/drinks meetings.

    I have a job that also often includes a number of external meetings – regularly over food – and where it’s often desirable to have that senior leadership present and pleasant. I had one job where my boss knew those types of meetings and “playing nice” were not her strength. In my case, she’d usually make me take those meetings solo – no matter how much it would have benefitted from having her go. And no amount of pushing how important a certain dinner/lunch was would get her to go. Even if I got her to agree in advance, inevitably she’d call out sick and make me go.

    Given the power differential and who she was, the only way to actually get her to meet with those people was to aim for afternoon meetings in the office. “Leaning into” what worked best just had more success than changing who she was.

    1. Slightly Less Evil Bunny*

      Yeah, that sounds like a good choice, especially for those hosts who have already brought up skipping the meal. They obviously are no longer wanting to put up with the pain that is dining with this woman.

  30. mother_of_hedgehogs*

    “Lucinda, can I ask you something?

    Why do you do this? Do you enjoy it, or get something out of it, because I just can’t see the upside of it. It’s rather cringeworthy to cause such an unnecessary fuss, makes everyone at the table uncomfortable, and the clients/vendors/patrons are noticing, and not in a good way.”

    I would love to hear that answer.

    1. Anne*

      You would make her feel bad and that makes you a bad person in her eyes. Nothing would change for the better.

    2. dz*

      “Hey boss, go easy on the staff, I don’t want you to end up eating a sneezeburger!” (Or sneezebisque or whatever term may apply, I don’t know fancy food.)

      1. tangerineRose*

        I’d like to know why too, but yeah, don’t ask her while she has power over your job.

    3. Jo Mitch*

      I wonder if this is all a power play – I wonder what she’d be like of eating out without clients. Is she just rude generally or is there something else going on?

  31. LawDog*

    She is C-suite, you’re not.

    Enjoy the networking opportunities and fine-dining. Stop skipping the opportunities. Take the positives and ignore the negatives.

    Saying anything to your boss about her behavior is a fool’s errand.

    1. bamcheeks*

      Enjoy the networking opportunities and fine-dining

      But you can’t when someone’s doing this! This would be the most infuriating part for me– I LOVE going to restaurants and the idea of going to lots of fancy restaurants where I could try different stuff would be amazing. But with a manager determined to ruin the experience for me and everyone else? I’d be so mad!

    2. Pastor Petty Labelle*


      OP is not in a position to change Boss’ behavior. All she can do is just mentally roll her eyes. Anything else could jeopardize her own job.

  32. teensyslews*

    I would say that if a standard of your industry is networking over a meal, and business contacts are beginning to skip meals as a result of her behaviour, then that is a real business reason to stand on! If your boss won’t hear it (and I suspect she may not) it may be worth bringing to her boss, or going back to a business contact who declines a meal due to her behaviour and asking them to pass that along to her boss. If your company is going to lose business due to her behaviour, that feels as actionable as if she was, say, being directly rude to vendors.

    1. teensyslews*

      Re-read and I see she is C-suite – is there another exec you have a good relationship and could talk to? If not, then stop turning down the meals, be excessively polite to both your hosts and the restaurant staff, and assume that they will remember your good behaviour as a refreshing contrast to your boss’s rudeness.

      1. Cara*

        I agree, the most I could see saying is “Client X suggested we take a coffee meeting instead of lunch, as they knew you didn’t enjoy the last meal and wanted to make sure you weren’t similarly uncomfortable with the next place. Does that work?” and then say, “If you’ve got a few places you’ve previously enjoyed, I’m happy to offer them instead”. Focus on making sure her enjoying the meal is central to all communications.

  33. Princess Peach*

    Oh, I see you work for my former boss! In her case, complaining about everything and trying to impress people with her inconvenient alcohol choices were part of the fun. No restaurant out there would meet her standards because she didn’t want good food. She wanted to look important and order people around.

    Our vendors & partner companies also stopped taking us to meals or bringing in food. Alas! There was no fixing her though, and I can’t blame them for not wanting to waste money and time on the Performativly Dissatisfied Boss show.

    I’m sure she’s still out there whining about the wait staff and wondering why people keep refusing to eat with her. I went to grad school to get away from her, and I’m much happier working in a whole new industry.

    1. Not Tom, Just Petty*

      Yes! This hit me, too. It’s not about finding the best food and drink out there, it’s about making the most demands and getting the most attention!

  34. Bunny Girl*

    You must channel your inner Violet Newstead and put rat poison in her coffee.

    Obviously don’t do this but I hate your boss. Is there anyone above her you would be comfortable talking to?

  35. pally*

    Could it be that the boss has some wacky notion that behaving as she does will impress the clients and vendors as to how ‘powerful’ she is?

    I sure hope this isn’t the case. Mortifying!

    1. Falling Diphthong*

      I suspect that this is it. She’s play-acting how she thinks a person confident in herself would act.

      Whereas in a skilled impov troupe, this would NOT be the set of moves that illustrated “most powerful and competent person in the room.”

  36. Emotional support capybara (he/him)*

    Food nerd and future chef here! Your boss is trying to game her way into free stuff at best and at worst is just an asshole for assholery’s sake. I don’t know what you can realistically to do make her cut it out that she won’t bite you for, but there it is.

    1. Silver Robin*

      I love your username and am now wistfully imagining a life with an emotional support capybara <3 <3

  37. Seashell*

    It’s probably for the best that she doesn’t go to a restaurant more than once, because the waitstaff would be fighting to get her out of their section and the servers would be tempted to spit in her food when she returned.

    I would be very embarrassed by all this and would avoid the dinners if at all possible. Looking for another job would be on the menu.

    1. A Significant Tree*

      I think it’s telling that she doesn’t consider any restaurant good enough to go back to, and also she’s usually in charge of picking the place (so can avoid going back to the restaurants where she’s burned a bridge or two). I wonder what she does if the client suggests a restaurant where she’s misbehaved recently.

      To paraphrase, if you eat at one bad restaurant, you’ve found one bad restaurant. If you only ever eat at bad restaurants, there’s just the one common denominator.

      1. londonedit*

        Yeah. I have a friend who doesn’t behave badly in restaurants, but the list of places we can go is always dwindling because she always finds something wrong with every place eventually. She’s a very picky eater to start with, but we’ll go to a particular pub or restaurant once or twice and she’ll seem fine, and then after the third or fourth go this will be wrong and that will be wrong, she’s sick of eating the same thing every time she goes there (meanwhile I’m vegetarian so I’m perfectly used to only having one or two options wherever I go!), she didn’t like the thing she chose last time, she’s found something to pick on about the service or the prices or whatever, and in the end I get tired of hearing her moaning about it all so I mentally cross that place off the list of places we can go to. Generally unless it’s really bad I’ll just get on with it – for me, while I love food, it’s more about going to the pub with a friend and catching up and having a few drinks, and the food is secondary. I don’t mind always having a veggie burger if we go to the Red Lion, or knowing that there isn’t much I like at the Lamb & Flag so I’ll just get a bowl of chips and have something else at home. But my friend doesn’t seem to be able to see it in the same way.

  38. Marzipan Shepherdess``````*

    OP, you should NOT have to take this on yourself, but are you in a financial position to surreptitiously slip the server a few extra dollars on your way out? That won’t make up for your boss’s insufferable behavior, but it might let the waitstaff know that YOU realize that your boss was behaving like a dingbat and that you want to compensate them at least a little for having to put up with her.

    Again, it should not be up to you to pay extra for a workplace-sponsored meal, but IF you can do this without taking a financial hit that you can ill afford, it might be worth it.

  39. MicroManagered*

    I supported myself as a server throughout my 20s, so I already knew about all the awful things your boss is doing.

    But this one, is freaking unhinged!!!

    Instead of ordering dessert, she will start her meal over and order a cocktail and appetizer while everyone else drinks espresso, a move that usually confuses our dining companions and also can throw off the servers, not to mention it extends the meal another 30 minutes or longer just when we were close to wrapping things up.

    The only time I’ve seen people order apps after their meal is like, if they’re camping out to watch a game or something. WTAF lol.

    1. Bunny Girl*

      I very admittedly didn’t last long as a server… entirely because of unhinged behavior from customers.

    2. 34avemovieguy*

      Of all the bizarre behavior, this is the one that will keep me up at night. I just can’t picture it. I can’t imagine having like crab cakes after eating a full steak or whatever. Like it’s so bizarre my mind can’t compute it.

    3. Elle*

      This is insane, but I have enjoyed a meal so much that I asked for “another round” of what I’d just had.

      But it wasn’t at a business meal. I’m not gonna unhinge my jaw for sandwich #2 in front of an employee.

    4. Anne*

      What is so odd about ordering an appetizer instead of a dessert?

      I am not used to eating at restaurants but I do remember once being in a group of young people who all ordered dessert (ice cream) first and then afterwards splitting the main course (some portions of tacos I think). But we did ask and the waiter laughed. And it wasn’t a fine dining place.

      1. Silver Robin*

        It is out of sync with the norms in the US and makes it look like she is restarting the meal when it is about to end. That said, cheese as dessert (post main course) is a thing in a few European countries so the idea of savory after savory is not unheard of. If it suits you, I honestly see no issue. But I doubt boss is acknowledging that it is unusual for context and adding extra confusion increases awkwardness

        1. wordwords*

          Yeah — you do sometimes see things like cheese plates for dessert at some European restaurants in the US, but it’s not super common. But ordering something off the appetizer menu for dessert would be eccentric, and enough out of step with the standard expectations of the meal that it’d be worth giving your server a heads-up that you were thinking to do it and/or picking something quite simple rather than something that’ll take a lot of prep and cooking, but not inherently an asshole move IMO. (Though because it’s so unusual, I would couch it as “I know this is weird, but I love to finish a meal with something savory, is there any chance I could get X instead of a dessert…?” or something personally.)

          But it’s the fact that this is coming after all the other nonsense that really puts the cap on this and makes it seem like she’s fully trying to hit the reset button and start all over again.

          1. Hot Flash Gordon*

            The cheese course is before (or instead of) the desert course and alive and well in France. It’s meant to encourage you to linger at the table and enjoy the company of others. It’s usually not a huge portion, just like the subsequent desert course is usually something smallish as well. Personally, I wasn’t a fan of eating cheese after a big meal and before eating something sweet, but I did like the digestif at the end of the meal (usually port, Lillet, cognac, or even jaggermeister) because I don’t like to drink coffee at night.

      2. Orv*

        It’s a little rude if you have other guests who are waiting to leave. Desserts usually come out quickly, since they’re mostly prepared ahead, but appetizers take longer. Everyone else will be done with their digestif and you’ll still be waiting on your jalapeño poppers.

      3. 34avemovieguy*

        Usually you order dessert at the end of the meal because symbolically it allows for the parties to end their rendezvous on a sweet note. Desserts are usually pre-prepared and easier to serve at the end of the night. Also, it could cause a backup in the kitchen if suddenly the kitchen has an order for the chef to prepare who has other orders to prepare for other tables, rather than the server getting a slice of cake. I mean this is all speculation but I can imagine it disrupts the flow for the table, and has the server revert back to duties they should be finished with. I also just think it’s in poor taste for a business or more formal situation. That’s just not the structure for meals and to me shows a lack of consideration for the people around you. Eating a small piece of cake (or sharing among the table) is quick and signals to everyone that the meal is wrapping up.

      4. MicroManagered*

        I’ve seen people order dessert first. It’s not super-common but it happens. I dunno man, dessert before main course I can understand. Ordering a main course and then an appetizer is … just different!

    5. Seven hobbits are highly effective, people*

      It strikes me as entirely reasonable bar behavior and unreasonable restaurant behavior. Like, there are plenty of times that a group of us hanging out at the local dive bar will conclude that we want another round of whatever we’re drinking and also a basket of tater tots to share after we’re done eating our meals, but I wouldn’t do that at fine dining restaurant. But I’m thinking of the kind of bars are designed to be places where you loiter in groups and order drinks, with eating a meal as more of an optional side activity, rather than eat a structured meal with a specific cadence to it. (I don’t think my local dive bar even has a dessert menu, but it’s also never occurred to me try to order dessert there so maybe I just haven’t noticed it.)

      1. Seven hobbits are highly effective, people*

        For clarity, the rest of it (being overly picky and obnoxious about the food and cocktails) does not strike me as appropriate dive bar behavior, just the ordering more drinks and savory apps after the meal part.

      2. Orv*

        Sure. Sometimes at bars like that I never actually order an entree, just a steady stream of appetizers. ;)

    6. NoMains*

      I know quite a few folks who do this every so often, usually when it’s a group of folks and particularly if sharing plates. The meal may start with a few apps or start with a few mains, but end with lots of apps. Wait staff are warned when they arrive though.

      I have another friend who often starts meals with a dessert then has 2-3 apps as her meal. I’ve been known to have soup + potato + app or soup + 2 apps for my meal – I will order it all at once and have no problem with it coming that way, or soup first then the apps – but every so often the servers/chefs/staff decided to bring one dish per course. I’ve had this happen even if no one was ordering dessert, so I had to choose between canceling something I’d already ordered or making everyone wait. If I do this now I specify I’d prefer everything to come as my main, or soup first then the rest as my main so this doesn’t happen.

      You’d think they’d be used to having folks order a bunch of apps as the meal – it’s pretty common for folks to do it at least some of the time among my friends group, but apparently we’re all weird.

  40. Decima Dewey*

    I’m a foodie who’s kind to servers and restaurants. So many people treat servers badly. Calculating the tip, they say “X didn’t do that much.” X provided prompt and unobstrusive service, but didn’t do it while riding a unicycle and juggling torches.

  41. Student*

    I have a relative and a colleague who are both like this. Let me explain a key concept to help you understand what is happening.

    Your boss has a hobby.

    That hobby is complaining about restaurant service and bullying/scamming wait staff.

    You need to understand – her hobby is not “foodie”. She wants to complain, be obnoxious, and feel like she got one over on somebody else. She enjoys complaining about food other people cooked; not the act of eating out at restaurants.

    There does not exist an option where she quietly enjoys a meal with you or your business colleagues. Complaining is, to her, the point of restaurants. The cruelty is the point.

    1. Sled Dog Mama*

      This 1000x.
      My mother in law has a hobby too. Her hobby is being unhappy about something, I refuse to eat at restaurants with her because of this.
      Incidentally I initially thought OP might work with my MIL.

  42. e271828*

    Does this rudeness really have no effect on how your clients and vendors view your company, LW? It would for me. At the very least I would try to avoid dealing with your boss.

    1. pally*

      Makes ya wonder.
      I bet those vendors dread having to dine with this woman. But for the good of their business, dine they must.
      If I were one of those vendors, I would suggest brown bagging it for any meals with this boss.

    2. Hlao-roo*

      Yeah, in the last paragraph the LW wrote:

      While I know her poor manners are a reflection on her and not me, I have noticed that our hosts are more frequently asking for me to pick a restaurant I think she’d find “acceptable” or suggesting that we “skip the meal this time.”

      The hosts (vendors and clients) definitely do not like dining with this boss. So far, their opinions might be limited to the boss’s dining habits but if the behavior continues it could sour some of them on the whole business relationship.

  43. Essentially Cheesy*

    Regardless of the amount of power the Boss holds, I am sincerely surprised that this hasn’t cost the company business and that vendors still invite her to lunch. OP/LW I am so sorry. It’s time to speak up and have an honest and gentle yet frank conversation.

    1. Observer*

      Well, I’m not convinced that it hasn’t yet cost them business. But even if it hasn’t YET, it seems pretty clear that is will. Hosts are already commenting on her behavior and asking to “skip the meal this time.”

      *This* is what I would bring to any other member of the C Suit (or CEO, who generally outranks the rest of the C Suite) or owner.

  44. too many dogs*

    Former server here. Figure out a way to apologize to your wait staff, so that they know you are aware of this bizarre behavior, and that it’s not their fault. Pretend to go to the restroom and find them. Apologize, and compliment them on their professionalism and patience. Even better, when leaving, stop by the hostess station and ask to speak to the manager on duty. Compliment their staff on their patience, professionalism, and hard work. If the Foodie is standing next to you, you just sound really polite. If the Foodie has already flounced out, you may mention that your table had some challenging people, and the staff was great. If the other guests you were with hear you, that will validate that you are nothing like your boss. Bonus: the hostesses will hear this and will tell everybody else on staff. Consider leaving an extra, cash, tip by your place. If you do it without being noticed, leave a polite note complimenting the servers. At the very least, the staff will realize that you are nothing like this woman. At the best, they will feel better knowing that somebody acknowledges the difficult time they were subjected to.

    1. Silver Robin*

      Oooh I like the tip about talking to the host stand/manager on your way out. Be an extra scrupulously good customer to balance the boss out.

      My only vague concern (not sure how much weight to give it) is that if the boss is there while OP is talking to the host stand or manager or whoever, she will cut in to undermine OP “actually xyz sucked and this was wrong and and and”. And/or boss sees it as OP undermining *her*, by disagreeing, or cutting in with something like “no honey, let me teach you how to handle waitstaff better” if she feels in a mentor-y mood. The main point is I can see a bit of a conflict happening if boss is around when OP is doing damage control, but I do not know boss, so OP can do the risk assessment.

    2. dz*

      If the external partners are paying, don’t leave an extra tip! You’ll be implying they weren’t generous enough.

  45. H.Regalis*

    Foodie, my ass. Pretentious jerkiness does not a foodie make.

    LW, I don’t think you can do anything to get your boss to change. You’d have to have authority over her, and you don’t. Do your best to ignore her bullshit and embrace the networking opportunities. I know it’s hard—I’d want to claw off my skin sitting at a dinner with your boss too—but do it if you can. If you keep getting asked to find a restaurant she likes, find a diplomatic way to say that that’s not possible.

  46. Ms. Norbury*

    No further advice, OP, only my deepest symphaty. I seriously hope your boss one day gets called out for her ridiculous behavior by one of the clients hosting her, preferably very bluntly, with a follow up conversation with her boss.

  47. Heffalump*

    I wouldn’t hold my breath that she’ll be receptive to criticism, even constructive criticism, from the LW.

  48. DD*

    My first thought is to preemptively tell clients or vendors inviting her out to dinner that she’s a PITA foodie (said in more professional terms) so they are aware. They may have relationships with restaurants they frequently use for business needs and can provide some heads-up to the staff. Also they aren’t blindsided when she starts showing her a$$.

    If it’s a client or vendor who has previously experienced her behavior asking for suggestions, I would basically say she is always like this, wherever she goes there’s going to be a show (once again said in a professional way). Knowing whatever is chosen won’t be “good enough” takes the pressure off them and they can practice their bland blank faces in response to her I’m a foodie show.

    Curious to know if this is just a weird foodie thing or is she boorish and obnoxious in other ways?

  49. Empress Ki*

    It is notorious that difficult customers end up with spit and snot in their food/drink. Maybe tell her this, it would make her think twice.

    1. Emotional support capybara (he/him)*

      I would not jeopardize my sanitation and safety certification for the sake of petty revenge but I would absolutely spend the rest of my shift hoping every meal they ever make themselves and serve to friends or family has a hair in it.

  50. Peach Parfaits Pls*

    Ahh yes, the “foodie” who seems to hate all food, drink, and dining experiences.

  51. theletter*

    I’m all about giving people the benefit of the doubt – maybe she is really is this picky, but forgot that when she’s at a business event, she really should be focused on the business. If they see her being distracted by a cocktail order or a dish that’s ‘not quite right’, they could get the impression that she’s not engaged in the main point of the outing.

    We all have moments in our lives where just have to get a grilled cheese and coke and move on to more important stuff.

  52. Everything Bagel*

    Who orders additional drinks and appetizers when the meal is clearly over and everyone else is having their after-meal coffee or dessert? Does she eat all of the food she orders? Is this food that people from outside your company are paying for? Your boss sounds like a plain old asshole, sorry. Allison’s suggested comments are reasonable and all, but if your boss is this type of asshole, I’m not sure anything you say is going to help. Just know that everyone knows you are not the problem.

    1. londonedit*

      I don’t know that that’s hugely egregious – I spotted above that people were saying cheese isn’t usually an option along with the dessert menu in most US restaurants, whereas it would be here, and so I can quite easily imagine that if someone doesn’t want a pudding they might order something cheese-course-adjacent from the starters instead. It might strike the waiting staff as unusual, but they wouldn’t think ‘Oh wow this person is starting their whole meal again’. And I also don’t think it’s odd to order another drink while people are having coffee – I’ve done that many times before, ordered cheese instead of a pudding and another glass of wine to go with it while everyone else is having their sweet things.

      But that might be a cultural thing. And I agree that if it’s just one of the many things that’s putting clients off wanting to go to a restaurant with her, then it’s causing a problem.

    2. 1-800-BrownCow*

      Me! Me! Me!

      I’m usually not hungry at the end of my meals at restaurants so I rarely do get anything. But also, I’m not much of a sweets person, so if I did really want something I would likely choose something off the appetizer menu instead.

      I’m also not an asshole, and always treat the staff very well, so maybe people eating me might now might not care. It might seem strange, but probably wouldn’t give it too much thought.

    3. Everything Bagel*

      Browncow and Londonedit, I certainly wouldn’t think you were assholes if we were friends and all went out together for dinner and you got what you wanted after the main course. I’m looking at this manager as an asshole for the entire show she puts on, especially if she’s ordering lots of extra food and drinks on clients/business partners’ bills. Read the room lady, you’re the only one complaining about the entire meal even the drinks all the way through but you just keep ordering more food while everyone else is winding down? That’s one big difference between her and the two of you, I’m sure.

  53. Cinn*

    Is it bad I want to suggest that you only ever go to business lunches at only one restaurant? Make your boss go to the same place each time to deal with the consequences of her misbehaviour. (I doubt she’ll change her tune if she realises that these people can mess with her in the future, but you never know.)

    1. pally*

      I wonder how much the restaurant may actually do as a consequence of prior boorish behavior. Sure they might refuse to seat the boss and those in the party. Maybe deliver poor service.

      As for tampering with the food in some fashion, that’s a mighty risk to the sanitation permits and all. Is this customer worth that?

  54. Csethiro Ceredin*

    I know some people are rude to service workers and I hate it, but even aside from that it’s so bizarre that she doesn’t realize how insulting she is being to the business contacts who are hosting her! If she has this little social sense she is probably not capable of learning and changing.

    On the plus side I’m sure it’s clear to everyone that OP isn’t participating. Getting in some compliments on the food and service would probably underline that and make OP feel a bit better.

    This is Arnold Rimmer and the Gazpacho soup, and it’s going to go just as badly for the boss.

      1. Csethiro Ceredin*

        I’d like to think performative assholery rarely does you any good, but…

        *gestures at everything*

  55. AnonInCanada*

    With that attitude, I wouldn’t doubt this boss had her meals garnished with some “Fromunda” cheese on more than one occasion. Anyone who’s seen the movie Waiting will get the reference.

    Alas, I don’t think there’s much you can do to mitigate this behaviour. You boss is a pretentious snooty snob, and she likely takes pleasure in treating people whose job it is to please the way she does. It’s a power trip. I hope her reputation doesn’t get associated with you on a personally with these clients/vendors. I’m sorry you have to deal with this.

  56. HB*

    I think there’s value in you continuing to accept the invitations and basically act opposite to her. There’s also safety in numbers – so you’re helping the clients/vendors by being on team Knows How to Eat at Restaurants. I think perhaps because of the embarrassment you’ve felt you’ve been quieter and more reserved, but there are lots of things you can do that don’t directly call her out for her behavior, but will help mitigate it. If she complains about the food, you can cheerily say that you think yours is delicious. Be effusively gracious and polite with the waitstaff, etc. It sounds like overall she’s not super argumentative – she’s just… difficult. I think that’s a *lot* easier to counter – particularly if the rest of the table picks up on it and starts exhibiting the same energy. My guess is it will be a lot easier on the servers as well because they know when they come to the table that there will be one highly unpleasant person, but several more aggressively pleasant people.

  57. Dandylions*

    I handle this by making comments like:

    My cocktail was fantastic!
    Oh no! Well my food is delicious!

    Etc. Basically acknowleding to the staff they are doing well.

    1. Everything Bagel*

      I agree with this comment and others like it. I don’t think there’s anything OP can say to the boss that’s going to make her act differently. If you openly compliment your meals and drinks and are gracious to servers, perhaps others will join in and it may even make it painfully obvious even to her that she is being the naysayer at the table. Or she’ll just think you have terrible taste and won’t let you ever pick a restaurant!

      1. Aspiring Chicken Lady*

        Yeah, I would do a “I think I’ll have this special drink listed on the menu – I love the adventure of letting professionals surprise me with their expertise, rather than sticking with something I’ve had before.”

  58. Shopping is my cardio*

    I can’t think of anything else to say that hasn’t already been said, so I would just reinforce that someone else at the company needs to go to these meals. A higher up with the power to put a stop to that. If that is not an option, just sit as far away from her as possible. If everything fails maybe discreetly suggest to the vendors to do cocktail hour instead. Ugh, this just sucks.

  59. DCer*

    Is your boss like this when you’re dining without clients or vendors? I wonder if someone once gave her some very bad “advice” to appear to care a ton about details while at business meetings because your dining partners will think you’re that way all the time and that you’re paying attention to details on their behalf when they’re paying you. When I read this note, that was what jumped out at me — its a routine I’ve seen people do over the top after getting that terrible recommendation for old guys who existed in a world where men complaining about their steak was much more kindly looked upon.

    If that is the case, perhaps helping her see that worldview has evolved would be helpful.

    1. AnonInCanada*

      She’ll bring the cheap-ass rolls. :-P Then criticize everyone else’s dish because it lacks “something” though she won’t say what.

  60. Czech Mate*

    My mother in law (as much as I love her) is like this, even though she’s otherwise usually a very nice person. There’s actually some growing evidence that extreme pickiness about food is rooted in neurodivergence and anxiety, and being “particular” about one’s dining experience CAN be a convenient cover for that. As a woman in the C-suite, she may also have gotten into the habit of “speaking up” even when it’s uncomfortable for herself or everyone else, and that may serve her well in her role but not in her everyday life. Honestly, as a woman in power, it may be another way that she feels she needs to “flex” her authority or show that she has some control in her life. I know those things can be true of my MIL.

    You may not be able to say anything directly to your boss, but thinking of this in your mind as her defense mechanism may help you address this. Maybe she doesn’t actually like business lunches or dinners because she has to “perform,” and so maybe she would secretly appreciate it if you try to prevent them. Maybe you DO just find a list of restaurants that your boss likes and steer her to those preemptively. Maybe you try to have snacks your boss likes during meetings so that she isn’t as interested in eating during the official working lunch/dinner. Maybe you intentionally try to make sure other events are scheduled immediately after the lunch so that there’s no time for a cocktail/extended lunch (“Oh sorry, we’d love to stay for a full meal, but we can just have an appetizer!”). My guess is that as obnoxious and rude as this is, it has some roots in her feelings of control/anxiety, and thinking of it that way may help you mitigate it.

    1. Observer*

      My guess is that as obnoxious and rude as this is, it has some roots in her feelings of control/anxiety, and thinking of it that way may help you mitigate it.

      It doesn’t matter WHAT the root is, her behavior has gone waaay off the deep end. And even if the LW actually knew what the root is, it would not be reasonable or realistic for them to try to “mitigate” it. Given that she actually has zero way to have even a clue as to the root of the Boss’ incredibly bad behavior, trying to find ways to “mitigate” her issues is a fools errand, and on a good day, a recipe for frustration.

    2. RagingADHD*

      Can we please stop with the automatic assumption that rude people are neurodivergent? It is boomerang ableism – when you go so far trying to make allowances for people that you come back around the other side by assuming that ND people can’t have good manners or behave decently in public.

      Whatever else this woman has going on, she has enough executive function and social savvy to become a literal business executive. If she were incapable of moderating her behavior to different contexts, she would act this way to everyone, not just servers. She could be polite if she wanted to.

      1. LLama Doc*

        thank you, boomerang reference needed. Most obnoxious people are not neurodivergent, or whatever diagnosis du jour, they are just crap people.

    3. Nightengale*

      I’m neurodivergent in ways that impact eating at times and. . .that could be a piece of it but probably a pretty small piece.

      There’s a real difference between not loving what you get and not eating a ton of it and loudly hinting it’s “missing something.”

    4. Librarian in Boxes*

      As someone that is anxious and neurodivergent AND as someone that has worked in a restaurant where her neurodivergent ways were weaponized against her, this is not constructive advice.

      As RagingADHD* says, this is boomerang ableism. And servers and hosts do not deserve to be punching bags for this woman and her colleagues/employees do not deserve having to deal with her mess.

      1. Observer*

        And servers and hosts do not deserve to be punching bags for this woman and her colleagues/employees do not deserve having to deal with her mess.

        This! 1,000 x over.

        It’s not ok for people to abuse others, even if it’s because they are “anxious” or “tired of performing ~~whatever~~”. She may not be physically abusive, but she IS being genuinely abusive, and if she REALLY cannot behave otherwise, she needs to not go out to restaurants.

    5. The Unspeakable Queen Lisa*

      You’re being very kind, but also enabling. There is no excuse to be rude and nasty to people with less power than you. “It makes me feel good to hurt others” is not acceptable in anyone, ND or NT. I’d also point out this woman is *not* picky about what she eats, she eats it all while bitching about it.

      Also, just… poor lady in the C suite pity party is not sitting well with me either. Yes, she clearly has control issues. I don’t care. That doesn’t entitle her to be gross.

      1. MsM*

        Especially when if she’s able to keep those control issues in check enough to not be a horrible boss the rest of the time, there’s no excuse for not doing it just because she’s hangry.

  61. Pool Noodle Barnacle Pen0s*

    My main question here is, how is this not affecting her reputation? I can’t imagine that her executive peers in whatever field y’all are in aren’t clocking this behavior and drawing conclusions about her professional judgment based on it. There is no way that this is just an isolated quirk. It speaks to who she is as a person and as a leader.

    If/when you do leave, maybe bring this up in your exit interview? “By the way, I would want someone to tell me this if I were you. Your behavior during business dinners has had, and will continue to have, serious negative effects on your professional reputation. It wouldn’t hurt to do some reflecting.” Or something. IDK, maybe it’s a bad idea or just pointless, but it might help her in the end.

  62. K in Boston*

    In addition to all the sage suggestions, I’d play robot and basically just pass on what the hosts are saying and let her connect the dots herself (which she probably won’t, but you’ll at least have done your part in communicating the facts to her) — “The folks from BigCo asked me to pick something you would find — hmm, the wording they used here is ‘acceptable to you’? — so I was thinking this place that seems pretty tried and true” or “Wilfred and Wilhelmina from Business Inc. suggested skipping business lunches in the future.”

  63. Impending Heat Dome*

    This is a tricky situation, since LW’s boss has authority over them and, as other comments mentioned, LW has to work with this boss daily, so confronting the boss about this would be a minefield.

    I think LW’s best course of action is just to be over-the-top pleasant at these dinners. Be super polite, use all the “May I?” and “Please” and “Thank you” humanly possible, compliment the server on your meal, tell them how much you appreciated them. That will make the boss’s bad manners stand out even more.

    Since these are mostly client and vendor dinners, *they* have the best opportunity to speak up to your company about Boss’s behavior. I really can’t imagine what Boss thinks she’s accomplishing by behaving this way in front of business partners, especially when she’s *their guest*, but it can’t be anything good. But LW playing up their own good manners will, at the least, send the message that it’s a Boss thing and not a Your Company thing.

    Other than that, I’d say it’s out of LW’s hands and any fallout has to come from above. Hopefully a client or vendor will speak up about it.

  64. DannyG*

    Had a friend in college who was like this. Eating out with him was always a pain. His dad was a big time insurance executive and I wonder if he was displaying learned behavior. I had hoped to meet his father, but he ( the father) died before graduation so I never got to see him in action.

  65. NMitford*

    I use to date someone who was an absolutely awful restaurant guest (like snapping his fingers at the servers and being extremely condescending to them), and he was shocked! shocked! when I gave that as one of the reasons I was breaking up with him. It’s hard to date someone when you can’t go to any restaurant without being mortally embarassed by his behavior.

    1. Heffalump*

      I once read something by a woman who said that on her first date with a guy, he lined up a bunch of dollar bills on the tablecloth. They were going to be the tip, and then he took a bill away every time the server committed a perceived infraction. He explained to her what he was doing. Her first date with him was her last date.

      1. Pizza Rat*

        I would have walked out.

        What do you want to be he ordered for his date? This story just screams psychopathic control freak.

    2. 1-800-BrownCow*

      A date that treats servers, or any other person working any type of customer service job, poorly is a HUGE red flag. It’s usually a telltale sign of what type of person they are and how they’ll treat their long-term partner in a relationship.

  66. Ms. Murchison*

    I lean towards following AAM’s plan B and following the advice of the commentariat about make things easier on the waitstaff. The boss is defined her identity around something she’s ignorant of and bad at. Unless the LW can find someone above the boss who is willing to order her to behave, I don’t think any critique will improve the situation.

  67. Tired Assistant*

    Any chance you can talk with your coworkers about the hilarious story you read on AAM about the crazy boss who doesn’t know how to behave in a restaurant where she’ll overhear you? Might be a good way to open the conversation door – just comments that might make her think a bit?

    “Apparently this lady doesn’t know that ordering appetizers for dessert is weird and awkward.”

    “She’s very rude to the wait staff – I’d worry about being a victim of those internet horror stories of someone spitting in my food!”

    1. Emotional support capybara (he/him)*

      I imagine a few of her servers have had daydreams about her meeting an end like his…

  68. Scott*

    Ugh. This just sucks.

    I’m sorry, OP. I don’t realistically think there’s much to be done, but YIKES. I’m sorry you have to put up with your boss’s nonsense, and I agree that this doesn’t reflect poorly on you – only on her.

  69. RagingADHD*

    Don’t miss out on networking because of this! Sharing a meaningful look about someone else’s bad behavior is a fantastic way to establish rapport quickly.

    If you can’t fix her, use her to establish yourself as the reasonable one that the business contacts would much rather be dealing with. After all, it sounds like that’s already happening with people approaching you to ask you to suggest a restaurant.

  70. WantonSeedStitch*

    I would absolutely not use any of the scripts Alison says for talking to your boss about this. Not because they’re necessarily bad–I might use those scripts if talking to a friend or family member! But not to your boss. Your boss obviously has a high opinion of herself, and criticizing her, even if you mostly have a good relationship, is NOT going to go over well, and could cost you. The only thing I might say is that if someone else is treating you to lunch and your boss talks about lowering the tip, you could say something like “I figure that’s up to Jane and Marcus, since they’ve so kindly offered to pay!”

    Instead of trying to fix her behavior, which is not going to work, do what Alison recommends more strongly: go out of your way to be warm and courteous to the server and express your gratitude. Also, do the same for whoever is treating you to lunch.

    Maybe others eating with you will pick up on what you’re doing and go out of their way to be kind to the server too, in which case your boss’s jackassery will stand out like a sore thumb and she might catch a clue on her own that such behavior is not admired. Definitely don’t laugh it off or play into her ego. If she makes a snotty comment about the food, don’t agree with her or say you’re sorry it’s not that good or praise her for her food knowledge. Just don’t respond. Change the subject. “I love this lobster salad. I remember when I was a kid, my family would stop at this lobster shack on our way to go camping…”

  71. Megaleío*

    Not THIS egregious but similarly, there have been instances where the person with the corporate card is questioning how much to tip, based on a real or perceived slight (“I had to remind him 3 times for my lemonade refill”), etc. I tell the employee (not my boss but peer or team member) that the corporate card represents the company externally, and that we should always error on over-tipping rather than under-tipping. We’re usually talking one or two dollars which is nothing against some perceived bias against a cheap company, when the serving team moves to the next job.

    1. JustaTech*

      I was recently reading the handbook for using our travel card for dining out while traveling for work and it says that tips are to be 15%.
      In an handbook from 2020!

      I said to heck with that, and if they want me to pay the difference out of my pocket, fine, but I’m not going to be a cheap jerk.
      (No one commented about it, but they did fuss that I didn’t have an itemized receipt for the Ruby’s Diner in the airport where my total was %20.53, a whole $0.53 over the “no receipt” minimum.)

  72. Michelle Smith*

    You could always kiss her ass a little while using the scripts, if that won’t make you vomit in your mouth too much. Meaning you could approach it by saying something that validates her feelings about the service or food but then follow it up with one of the suggested scripts. I’m thinking something like, “I know the service wasn’t up to par at X, Y, and Z, but because you voiced it, contacts have been suggesting we skip dining from now on. Do you still want me to suggest we go to X? I think folks would be comfortable with that, if you’re able to overlook [insert whatever minor issue she complained about last time here].”

  73. Festively Dressed Earl*

    “If you want the true measure of a person, watch how they treat their ‘inferiors’, not their equals” acts as a business justification for going over this boss’s head, since it’s unlikely she’ll take advice from an ‘underling’. Vendors are watching boss’s demands and her reactions, wondering if doing business with this person is worth the hassle. Clients are watching boss’s disregard for everyone’s time and effort and wondering if boss will be able to respect deadlines or play well with others long enough to get a project done. This is hurting company’s brand and may well cost them business, so someone boss respects needs to remind her how to behave in a business meeting.

    1. Office Plant Queen*

      Boss is c-level, so there might not be a way to go over their head depending on the situation

  74. 2 Cents*

    Sounds like an opportunity to have “just drinks” somewhere or have food at an office where there is no server, if food must be had at all. No wonder this person never frequents the same place twice.

    I had a former friend (loose term) who was an incredibly picky diner, and the rest of us compensated through tips, being overly gracious to the server, and also getting takeout instead.

    1. Office Plant Queen*

      “Just drinks” might be risky with someone like this. It can easily turn into alcohol on an empty stomach, which can be a disaster with even perfectly polite and kind people

  75. Observer*

    LW, I want to say that you should absolutely NOT skip these meals with her. Do everything you can to make and strengthen connections.

    Also, are you jog searching? If not, is there any reason? I know that some people are bad restaurant patrons without being totally impossible otherwise. But her behavior is SOOO out of line, that I suspect she’s difficult in other ways.

  76. herblondeness*

    OMG, are you dining out with my mother? Nothing ever good enough, wait staff are all idiots, the rest of us cringe at her bad behavior. No good advice that you haven’t already been given, OP, but you have my sympathy.

  77. JukeBox*

    It is not wise to irritate somebody who could spit in your food. Should Boss overhear you saying that in a private conversation? Probably not.

  78. Ana Maus*

    If she didn’t choose new places every time, I’d suggest, “Pick a place you know you’ll like so you don’t have to worry about sending things back.”

  79. Sugarholic Teacher*

    How old is this boss, I wonder? I knew someone who did this and it turned out to be an early symptom of dementia.

  80. Keep it Simple*

    I loathe people who are jerks to restaurant servers or cashiers or fast-food employees. Their jobs are HARD. I wouldn’t do those jobs unless it was a choice between being unemployed. I always say please and thank you and maybe a quick comment like “I like your earrings (or tattoo, or shirt, whatever.)” People who are jerks to service workers are just sucky human beings.

  81. BellaStella*

    To me this boss sounds like a narcissistic jack hole. Ugh

    Above commenters noted finding a place to eat that she likes but I say meet at McDo and make her suck it up.

  82. Crumbledore*

    My boss at a former job hired a consultant who never failed to send his food back every time went out for a meal. I did not get it, like, did he want to show us how much he valued our money (if we were paying for the meal), or just show off his discriminating palate? Either way, it was very off-putting!

  83. Office Plant Queen*

    I would LOVE to know what she cooks for herself at home. What does she actually like? Is she a good cook? Or is she just disappointed literally every time she eats?

  84. Fluff*

    I got these scripts for a PITA relative and a co-worker. Not a Chief. Maybe they might help if you know your boss.

    When she starts complaining about the custom drink, surprised look, ” Hey, they did you a favor, remember that wasn’t on the menu.” Look like a surprised child who reminded their friend to be nice. Like you are doing her a favor, in case she forgot.

    When complaints start:
    “that bad?” incredulous look, “Boy, you have like no luck at eating out.”

    If food complaints – feign surprise and “dude,” and wait. Again, ONLY if you can.

    When she reorders the main dish while you are all eating dessert, kindly and firmly suggest, “We do have a time limit, so we may have to go,” or suggest she get her re-ordered meal to go. “You might want that togo. I have to give X a ride” (insert time limiting factor here).

    At the end, leave an additional $20 and say in a nice voice – “I used to be a server and we were high maintaince today. I’m going to leave a little happiness. ”

    I have used the surprised “Duuuude,” and then apologized to my supervisor. It did help. I think the Duuuude surprised him.

  85. Looper*

    Don’t say anything because no one who behaves that way so consistently for their entire life is going to be open to feedback like that. Remember: her behavior reflects on herself only, and you are just doing your job by being in attendance; further, she is neither the first nor last annoying customer that restaurant/server will deal with; and also that server is not going to remember you or think about you enough to threaten your job over. Either learn to emotionally distance yourself from your boss’ behavior, or start looking for other work. Telling her that she acts (and has acted) like a jerk every time she goes to a restaurant is going to land exactly how it sounds. Don’t do it!

  86. Jay*

    The Chaos Goblin in me immediately remembered that there are restaurants were the waitstaff are permitted, nay, ENCOURAGED to let fly with streams of verbal abuse at customers who don’t mind their manners. It’s a big draw for people, as I understand things.
    Watching rude people get their asses verbally handed to them by someone they think is defenseless.
    And the clients are asking YOU where to take her now.
    Possibilities, possibilities, possibilities……

    1. RVA Cat*

      Now I’m imagining C-Suite Karen getting absolutely defenestrated by Gordon Ramsey.

  87. I'm the Phoebe in Any Group*

    This is going to cost your boss clients. Unless he’s got some really rare skill/product, many will take their business to someone who is not, as Alison says, an ass.

  88. Elio*

    She’s not a foodie, she’s a buttface. Plenty of adults and children can behave in restaurants. It sounds like she’s trying to get free stuff from the restaurants to me.

  89. LLama Doc*

    Did my mother come out of retirement? It’s juvenile, attention-seeking behavior. I personally would ignore her restaurant suggestions, go someplace tried and true, and remember her behavior is not a reflection on you.

  90. Jam Today*

    LW should watch “The Menu”. She will never change her boss’ obnoxious, adolescent behavior but she will derive some enormous satisfaction in seeing what happens to the boss’ film counterpart(s) after they behave similarly.

    (I laughed very hard at the end of that movie, if you like grim satire this movie is for you.)

  91. Jo Mitch*

    Your boss is awful – rude, attention seeking and missing the point of the meal. What you say depends how much you need this job but I’d be networking my way towards a new job. L Just another thought is there any opportunity where you can go for a meal along with clients, your boss and her boss – her boss might give feedback bluntly!

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