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Need Help - Etiquette for dinner w/boss

My boss asked my husband & I to dinner this Sat eve with she & her husband.
Just wondering who pays? We decided to come prepared to pick up the tab, but we also aren't sure b/c she asked us & it may be a welcome to the company kind of thing too, althought she didn't say that. May also just be more social too.

Thoughts on what to expect?

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  1. If the boss did the inviting and picked the place, I would expect her to pick up the tab.

    Why not just let it play out. When the tab comes, if the boss doesn't pick up the tab, offer to pay for dinner.

    It may leave a sour taste in your mouth ("egad, I work for a tightwad") but at the very least you'll (1) have learned your lesson about dining with your boss and (2) did a little brown-nosing, which never hurts in the long-run.

    Enjoy dinner.

    1 Reply
    1. re: ipsedixit

      Perfectly said.

    2. Remember the game follow the leader, here's a real life example.

      The first dinner with the boss is always a challenge.

      The major rule to remember that she is your boss, no matter how friendly this gets, she is your boss.

      Other rules/guidances to remember include:

      - that you are really not there to order something that may get you into a pickle. Wearing food at a business or quasi-business dinner is a bad event. So order something and ask your hubby to do likewise, that should not splat all over the place. Long pasta is a definite no-no.
      - do not try to be a show-off if you are more versed in food than her. "Oh that sounds good" is a great response to any questions on food. "Blech" should be avoided.
      - do not get tipsy or drunk. if your boss start throwing them back, do not go toe-2-toe with her. let it go and stay sober
      - as far as ordering, try to wiggle into her ordering first and see if she orders both an app and an entree. nothing worse than eating appetizers while the boss and her hubby watch
      - dessert, same as app, try to go second
      - bill. always offer to split the bill and see where she takes it. not sure about what your corporate policy is but keep an awareness about you. last thing you want is a call from internal auditors on why was this dinner placed on a corporate card.

      but try to be more aware on the first one, versus subsequent. she will do a bit of leading. try to follow (except for the drinking aspect).

      Good luck

      20 Replies
      1. re: jfood

        jfood, I heartily disagree with you on "always offer to split the bill..." In my book, that is a MAJOR faux pas! First off, in all probability the boss is on an expense account. Secondly, there is something "downputting" about such an offer because it implies that the boss' guest is concerned whether or not the boss can AFFORD to pay for dinner. DON'T DO IT...!!!!

        1. re: Caroline1

          C

          Jfood thinks it depends on the circumstances of the offer. There can probably be an equal level of presumption and level of faux pas if you are sitting on your hands and "expecting" the boss to pick up the tab. It's a Saturday evening, onethat many companies might feel is not on their nickel to pay for.

          Likewise the boss may be testing her direct report if she thinks that dinner for four on a satrday night should be a reimburseable company sponsored meal.

          With a higher level of scrutiny on T/E budgets and uses it is a very tricky position to be in.

          So although jfood is not agreeing with you, he is also not disagreeing because it once again come to that all important word seen hear (sic) so often, communication. And then the favorite answer, "It Depends."

          1. re: jfood

            Jay, once again I cannot agree with "it depends." If the boss is game playing and using a dinner invitation as a way of "testing," if I found myself in those circumstances, I would do my damndest to fail the test intentionally and look for another job. Bosses who like to play games to make new employees nervous aren't worth working for, in my opnion.

            BUT...

            There is no indication from the OP that this has been anything more than an invitation from the boss to go to dinner tomorrow night. And in that circumstance, I see no room for "it depends."

            Now, according to the OP, the boos has invited her and her husband to dinner on a Saturday night. Whether the invitation is proferred by one's boss or a friend, the etiquette is the same: when you invite someone to dinner, whether at your home or in a restaurant, you are inviting them to be your guest. No fee! The ONLY exception being if the person extending the invitation makes it perfectly clear that it is to be "Dutch" at the time the invitation is extended. That clarifies immediately that there will be out-of-pocket expenses involved, so if the recipient of the invitation feels this is not a good time for added expenses, they are able to decline.

            Offering to pick up the tab carries a whoooole lot of possible subliminal messages, none of them good: Does the guest think the host is in over his/her head financially and wants to bail him/her out? Is the guest being defensive and afraid the host is handing out charity? Is the guest concerned that accepting the gift of dinner from the host will obligate him/her to the host and the guest does not want to feel such an obligation? There are endless ways an offer to pick up the host's tab can be seriously misconstrued, and it is just so much better not to go there.

            1. re: Caroline1

              Okeedokee. agree to disagree. The last time jfood heard the "dutch" line was in high school and Nixon was President.

              Boy jfood feels silly looking back and thinking of all the times he paid his fair share for all those dinners that people called mrs jfood up and said. "Heh, how 'bout the 4 of us go out to dinner this saturday night?" And since they did not say "oh and just so you know you and jfood have to pay for what you eat" he should have kept his wallet in his back pocket. Could have paid for a year of college for little jfood.

              Jfood totally disagrees on the default being if not specifically mentioned that the caller is picking up the tab for the callee. The default is that if you call and make arrangements to go out to dinner as two couples that it is expected that everyone picks up a piece of the tab, that's the default and if someone calles and say, "Bob and I would like to take you and Tony out to dinner on Saturday night" then that is the exception to the rule. someone merely calling up and asking for a mutual dinner on a saturday night does NOT, in jfood's mind, constitute an offer to pick up the entire tab (other than at their club where money is not accetped).

              And to the last paragraph, jfood could come up with a list of questions as well, but he does not think these two donuts will overlap.

              Oh well, life goes on. Hope they have a good dinner and the two of us can await the reults on Monday.

              Have a good weekenend C.

              1. re: jfood

                No use turning a narrow situational invitation on its head and shaking it until it falls completely apart. The boss is treating. If the boss doesn't treat for some very, very weird and inexplicable reason then the OP needs to run as fast as the OP's little legs can take them away from this boss.

                1. re: Servorg

                  Sorry, but Jfood's answer of "it depends" and his original response to offer to split is the proper road to go down, in Jfood's opinion. If others disagree (and yes they have) that's cool, po-tay-toe, po-tah-toe. But it is not turning anything on it's head, in fact others are professing "scorched earth" if the boss wanted to develop a social connection in addition to a business connection with the OP and did not pick up the entire tab. Jfood thinks that's a head turning response, quit your job if your boss does not pick up a saturday night dinner. If little jfood ever told him that bit of wisdom, there would be a little fireside chat going on at casa jfood.

                  Jfood is merely stating his difference of opinion (isn't that what the OP was asking for re: "thoughts on what to expect"). He has gone out with many bosses over the years and there have been times when it is split and times when it is not. Pretty simple answer from lots of experience, once again jfood defaults to "it depends".

                  But the idea that if the boss does not pay let's pull a chicken little is not even in jfood's vocabulary.

                  1. re: jfood

                    One more vote for jfood.

                    If the boss made this as simple an invitation as the OP made it sound, the OP has every reason to think it is on the boss. I would still offer to split the tab, as a courtesy, if that seems possible and appropriate when the check comes. If you're new to the company I would think it's perfectly OK to be unsure of the 'rules'or intent.

                    I guess the only possible issue here is if the invite was really intended as a social splitting of the evening it could be awkward to only OFFER to split. Only the OP knows the full context of the invite, though, so she would be the one to decide how possible a split could have been. The OP paying would seem to be off the charts as a probability.

                  2. re: Servorg

                    Amen...!

                  3. re: jfood

                    Totally with you jfood. When my hubby and I go out to eat with friends, we spilt the bill about 80% of the time--doesn't matter whose idea it was to get together. Sometimes, one couple will treat the other, but we usually split down the middle.

                    If I invite another couple and we would like to pay, then I make that clear in the invitation, such as "we would love to take you to dinner".

                    In a work situation (and I've been both the boss and the employee), I am always prepared to pay. If I am the boss, I thank the other person for the offer and pick up the tab. If I am the employee, I am fine with things either way. Why would I expect my company to pick up a Saturday night meal unless I was entertaining a client or out of town on business?

                    Furthemore, we assume the OP works in a place that has an expense account. Having worked for my fair share of non-profits let me tell you there are plenty of places where the job would never pick up the tab.

                    1. re: Honey Bee

                      Don't you see that no one is disagreeing with jfood about how things can be handled among friends? But as the OP states, this is simply not the case here.

                  4. re: Caroline1

                    seems to me the FIRST time the boss invites, then one can safely presume the boss expects to pay. I don't really see the harm if after the bill sits there for a few seconds the employee offers to pick up the tab. the boss then should say something along the lines of "don't be silly, I/we invited you, or at least... no, lets split it. If it happens a second time offering to split would seem reasonable.

                    1. re: KaimukiMan

                      Yes. This is a "welcome to the firm, glad to have you working for me, lets get to know your spouse a bit too" dinner invitation. The boss is hosting you and your spouse. If you become social friends as couples then that can alter the situation with who pays/splits the check later on....but not this time.

                2. re: Caroline1

                  I second that. The "dance" when a bill is presented at a table with equal diners is always a difficult trick. But the OP's circumstance will not be equal diners. The boss is the boss. I'd absolutely sit on my hands.

                3. re: jfood

                  But shouldn't it be placed on a corporate card? Its still a work related dinner..isn't it? The boss is probably quietly judging/taking notes on the new hire to see what kind of person they are outside of work. I would watch how many glasses I had

                  1. re: DarthEater

                    Not in the company I work for (a large multinational corporation with a culture of ethical behavior that is constantly reinforced). Dinners are only on the corporate charge if you're travelling or entertaining a client.

                    1. re: DarthEater

                      Dinner on a saturday night with spouses/SOs is not a reimburseable expense at Jfood's company.

                      1. re: DarthEater

                        I have worked at several companies where this would have been rejected - we could submit travel and customer related entertainment expenses only.

                        I had one job where expensing department activities (eg, a team lunch during a workday meeting) was not allowed!

                        1. re: lisa13

                          Not only that but the most senior person at the table has to pick up the tab. This avoids the junior picking up the tab and the senior person, also at the table, approves this expense.

                          1. re: jfood

                            I used to work at a company where the team would go out for a meal, and everyone would chip in their share in cash. Oddly enough one of the junior execs would always charge it. Unbeknownst to everyone he would then submit it as an expense, and he and the senior exec who approved the expense would then split the cash "take". Such a stupid, petty reason to put your job on the line - and yes, when the truth came out, both of them lost their jobs.

                            1. re: KaimukiMan

                              that is apalling! And kinda funny, seeing that in the end they got their comeuppance.

                    2. I agree, follow the leader.

                      When my husband and I are entertaining clients/employees we talk out loud about the menu, "Oh, that filet Oscar sounds good...I can't make up my mind on an app, why don't we order a few-what do y'all like?..." We try to let our guests know-order what you want.

                      I know if my husband is inviting a new employee out we will be picking up the tab. We also let the restaurant know who the check should be delivered to so there will be
                      no awkwardness for our guests.

                      1 Reply
                      1. re: hipquest

                        This is exactly what we do as well.

                      2. Your husband's boss invited you, he is then the host and he will pick up the tab. Consider it an honor and that the boss thinks highly of your husband.

                        1. Hopefully your bossed is versed enough in etiquette to know that if she asked you both to dinner, she is the host and is therefore obligated to pick up the tab.

                          Unlike a few others who have replied here, do not offer to pay. I think it would be an insult.

                          2 Replies
                          1. re: marcia

                            Marcia, I'll agree with you that with the boss proffering the invitation, coupled with her being the boss, I'd expect that the check would end up in her hands. I'll also agree with the previous post that if the boss handled it well beforehand with the management, the check should be handled discreetly, quickly, and with no real opportunity for discussions about splitting it. But if there is that moment of uncertainty, I don't think that a quick offer to split it would be an insult.

                            There are subtleties: For example, if the invite was part of a conversation such as, "Oh, Jim and I were talking about how nice it would be for him to get to know your husband..." it makes it more a social than a strictly business dinner. Or if the poster was asked to suggest the restaurant, or brought it up herself. A simple motion towards your purse and credit card with a simple offer "Can we split this?" is far from disrespecting the boss's status or generosity. Just don't argue about it at all with an, "Oh, please let me split it," or worse "Can I get the tip (or wine, or drinks)." Also, avoid the automatic, "OK, but I'll get it next time," -- too presumptuous in that situation.

                            1. re: nosh

                              I agree with Caroline. When the check comes if they don't pick it up IMMEDIATELY and indicate they are paying, you have to at least make towards the book like you're going to pay. Then they either insist they are paying and take it out of your hands, or they let you pay and say they'll get it next time (which sounds like they want to initiate several dinners out, which I certainly wouldn't want but that's up to you) or, worst choice, they just say thanks, and then you don't go out with them again but at least you get brownie points for buying din.

                              I say no to apps even if they order them and/or are paying. It runs up the bill. If they order an app that should be plenty to share. No matter who is paying, it runs the bill up for both couples to order apps. Drinks, salads, entrees, dessert and/or coffee optional.

                              Boss should pay as she invited you, but if they don't, be prepared to at least offer to pay. Nobody splits the check unless it's a business lunch or you know each other very well IMO.

                          2. Chances are, the boss will -- and should -- pay. Even likelier, the dinner is on the company tab. You wouldn't be wrong to assume that. However, watch for cues. You may notice whether or not your boss pulls out her corporate card. Also, if the husband picks up the check, you should probably offer to split (since he's obviously NOT putting it on any expense account related to work -- assuming he doesn't work at your company.) If the boss hastily grabs it, you're probably in the clear.

                            Regardless, good luck and enjoy!

                            1. I think the problem I'm having with this situation is that this dinner is taking place on a Saturday night, which makes it seem more socially oriented than business or perhaps it's a combination of social and business.
                              I think, simply based on the OP's original confusion as to what the dinner represents, they should be prepared to pay their share, offer to pay, but don't argue if the boss insists on picking up the tab. Walk from the job? That's pretty extreme. Reconsider future invites, perhaps...unless they end up being a great couple to go chowing with.

                              1. I'd offer to pay my half when the bill comes - I would not pick up the whole bill. 9 times out of 10, the boss, who invited you, and who picked the place, is going to pick up the whole bill. Enjoy. Don't drink too much in front of the boss. Don't get too friendly. She's still your boss!

                                1. I'm inclined to agree with Caroline1, based on my assumption that there is not a strong social relationship between kparke30 and her boss. If the nature of their relationship is primarily employer/employee and the boss extended the invitation, then I would expect the boss to pay. The vibe I'm picking up is that this is still an extension of the workplace. Boss's rules, Boss's check.

                                  After they've settled into a more complex relationship with multiple social layers (could be days, weeks, months, years, or possibly never) interwoven with the working relationships, then it'd be more appropriate to offer to split.

                                  7 Replies
                                  1. re: ricepad

                                    HI There all, OP here - First of all, thanks for the spiriting responses, all are helpful!!

                                    I apologize for the the tardiness but in this case, the 'boss' also happens to be the owner of the company. It's a 100 person company & she said she wants to 'get to know' us better, new senior exec, etc. I think it's more social in nature but agree not to drink too much, watch for their lead, etc. They too are foodies & love to entertain (so she's said) so I think it will unfold easily. We decided we will be prepared to pay if necessary, or at least offer as we do not want to 'assume' anything since this is first time out with them. Doubt she'll be offended by a gesture & she may even say something before it ever has opp to be an issue.

                                    I will report back on what happens!! Thanks again.

                                    1. re: kparke30

                                      I guess the only question I have of you is the simplest one.......what it is that would lead you to conclude you should pay when someone else asks you to dinner...... business or not?? Possibly splitting the check I understand, but not how you and your husband should pick up the entire check.

                                      The only situation I can think of that would have ever led me to that conclusion was when I was a middle manager in a large corporation and my boss signed off on my expenses. He would sometimes have me pick up a check and turn it in to him so he could approve it rather than having to kick it up a level to his superior. Young execs - please forget I just said that!

                                      1. re: kparke30

                                        Have fun tonight K. New data (owner = her; sr exec = you). She will pick up the tab for sure.

                                        Enjoy the dinner and your new job.

                                        1. re: jfood

                                          Hi All, just to report back, boss did pay check. Check was presented to her husband who promptly took it & stuffed Visa in. Thankfully too as tab had to be at least $700. for apps, dinner, dessert, wine!!!
                                          I appreciate all the insight from my fellow 'hounds!!

                                          1. re: kparke30

                                            glad to hear it! so where did you go? what did you have? how was it?

                                            1. re: KaimukiMan

                                              In Boston metro West area, Framingham, 'The Rat Pack Cafe' located on Rt.9 behind Legal Seafoods.

                                              Sinatra themed supper club, complete with high backed leather booths, piano man, dark wood, etc. Began with appetizer for table which included shrimp, scallops, baby lamb chops, crab cakes, 6 of each between 4 of us; excellent all.

                                              NEXT....DH & I split a wedge salad, boss had a wedge salad, husband mixed greens. Wedge was good, nothing special.

                                              Entree for me was bone-in filet, DH was 'cowboy' steak (rib-eye), boss got mahi-mahi special, her husb duck breast special. I don't normally get filet mignon but thought I'd give it a try since had bone for extra flavor. Glad I did. Cooked perfect med-rare, juicy, nicely charred on outside. Husband's cowboy steak was huge, with bone. Other entrees I'm told were quite good. All had house veg of assorted zucchini 'spaghetti', cherry tomatoes, which were nice compliment & did not compete with entrees for too much attention. Dessert for us was cheesecake, for them was black forest type cake. Both seemed average.

                                              Total of 4 - YES 4 - bottles of wine throughout included Estancia red, followed by 3 of Krug red; all excellent & easy to drink, complimented meal nicely.

                                              Had wanted to try this place & was a nice place for this type of invitation. Service was a bit lacking which disappointed me. Waitress took too long to present herself after we were seated. Hostess did not offer to take our coats. Waitress seemed a bit cold with us overall, but warmed up as the evening went on. Brought our salads & none of us had silverware, which was not replaced after being cleared with the app plates. Waitress was somewhat helpful in pointing out the Krug red which was a special & turned out to be a highlight. Overall, service was decent but not what I would have expected given the atmosphere & frankly, how much we were spending. Place got quite noisy as crowd filtered in to listen to piano making it difficult to be heard unless speaking loudly.

                                              If I were to go back, I would either go early or late for dinner to avoid the crowd; to be expected I'm sure given it is a popular place on a Saturday night. Fun for a night out & leisurely meal in a room with an 'Old Vegas' glamourous feel to it.

                                              Overall I would recommend it but may not rush back very soon!! Thanks again to all.

                                              1. re: kparke30

                                                Thanks for reporting back and am glad boss paid, especially at that price. Dang!