how do I handle lunch with my boss?

A reader writes:

I am in the second real job of my career. It’s a great job with coworkers who respect each other, unlike my previous job, which was a place where everyone screamed all the time and the staff was underpaid and monitored by camera by the owner.

Several times a month, I am out of the office for meetings in the same neighborhood where my manager is having (separate) meetings. Maybe three out of four times, we’ll finish around the same time and travel together to the office. Most of the time this happens, my manager will ask if I want to get lunch first. I don’t feel any pressure either way, she lets me pick the place, and we enjoy each other’s company. She even picks up the tab about half of the time. It’s a good situation!

I have not been able to figure out the right amount of gratitude to show for the meals that she treats me to. I feel like working at my previous toxic job set a low bar for interactions with the boss, so my initial impulse is basically to grovel. Just a quick “thanks for lunch!” a couple times a month seems like not enough, but anything more effusive feels off. What to do?

You can read my answer to this letter at Vice today.

{ 80 comments… read them below }

      1. Jean*

        From the OP! “I am in the second real job of my career. It’s a great job with coworkers who respect each other, unlike my previous job, which was a place where everyone screamed all the time and the staff was underpaid and monitored by camera by the owner.” I’ve worked in some toxic places for sure, but no spy-camming that I was aware of. THANK GOODNESS.

        1. Diahann Carroll*

          Oh, I thought you were saying you also had this happen, lol. Reading too quickly there.

  1. Nanc*

    I have nothing to add to Alison’s excellent answer but dang, that graphic is a little disturbing!

      1. juliebulie*

        I thought the one on the left with twirly eyes and the tongue sticking out was gagging. Reflecting the theme that not everyone will eat the same food?

    1. Panthera uncia*

      The entire UX of that page is a horror show. The article content is the only redeeming quality.

  2. many bells down*

    The first time I had a boss take me to lunch he said “first things first: this is work time, so I pay and you put it on your timesheet.” I really appreciated him making it clear from the start because I was only about 25 at the time.

    1. No_woman_an_island*

      Very nice. My current boss, during my first week, insisted I go to lunch with her and a colleague as a working lunch to discuss a new project. She made it clear up front that we would all be paying our own tabs. She makes a lot more than me, and it was my first week. The gesture of picking up my tab would have gone a long way in keeping me here longer.

      1. sacados*

        Man, that sucks. I mean, it’s good that the boss made the situation very clear upfront, but it doesn’t say a lot of good things about the culture of that organization that people are expected to pay their own way for working lunches.

        1. No_woman_an_island*

          Exactly. When I got the opportunity to take my direct reports out for a celebration meal for meeting a milestone, I told them they were on the clock and I was paying. Little things make such a difference. Treating people as human beings goes a long way.

          1. Stormy Weather*

            I’m so glad you did that. People need to feel valued. Being forced to pay for a lunch because I was working is offensive. Your boss had the power and more money, they should have picked up the tab.

          2. Alina*

            When I was in college I asked an older student to get coffee to get advice about a class or something,m. She bought both our coffees and said she was happy to do it (buy the coffee and give me advice) because other people had done it for her. That’s something that has always stayed with me, and something I do now. A cup of coffee or even a lunch isn’t that much money but the gesture speaks volumes.

      2. Pay No Attention To The Man Behind The Curtain*

        Yeah, I’ve had a boss like that. He was an executive director 2 levels above me and he loved to have “his team” go to lunch together (“voluntarily”), but he picks the place and we all pay for our own share. His favorite place? A pizza place that serves…just pizza. We’d all have to chip in, in cash since they didn’t take CCs, for our 1-2 slices of whatever pizza toppings he was feeling that day. I was not sad when he lasted less than a year for other, more serious, shenanigans.

        1. No_woman_an_island*

          Yuck, sorry. It makes me wonder if some people have no self-awareness at all. Because the alternative is that they’re big jerks.

          1. LunaLena*

            I think, if they have that much of a lack of self-awareness, they’re already a jerk and that’s why.

      3. Artemesia*

        Working lunch, she pays. Only saving grace is she gave you the heads up. But in the OP’s case, where it is happenstance that they are traveling back and have lunch together, I would think that at least occasionally the OP should just say up front ‘let me treat you this time’.

    2. 1234*

      That’s awesome. If I am ever in a position to take a direct report out for lunch (or even get a direct report) I will definitely say something like that from the start.

    3. Faith*

      It’s so important to make things like that clear to newer employees. Sometimes I offer to grab a coffee for my intern (we have a cafe onsite, and I’ll go so I can get away from my screens for a couple minutes), and I’m always sure to tell them that it’s my treat. Ditto if I send them to get me a coffee and tell them to get something for themselves; I tell them AND I make sure I hand them enough cash to cover two fancy coffees.

    4. Mediamaven*

      I had an afternoon barbeque for my staff at my house – catered, pool, champagne, the works. The hourly employees all clocked out for it! I was like what on earth are you doing? You think I’m going to throw a work party and you get paid less because it’s during work hours? No. You can have fun and get paid as normal because it’s still a work event. I can’t believe some companies don’t get that.

      1. Panthera uncia*

        Nice boss or not, I can’t blame people for clocking out if there’s alcohol and a pool involved. Our H&S people would have an aneurysm just thinking about that.

        1. Mediamaven*

          It wasn’t anything crazy TBH. These are all young ladies who wanted to sip a little Rose and lay out on floaties and eat tacos. If I had to do that when I worked for someone I would have been miserable, but that’s what they like! No real room for debauchery.

            1. Diahann Carroll*

              Yup. I worked for an insurance company that said if you have alcohol at a work-sponsored event during work hours, you need to clock out and not come back to the office for the day. Under no circumstances could you have a glass or two of wine and then come back to the office for liability purposes – legal would have hit the roof.

              This rule was great for us exempt folks, but non-exempt folks who couldn’t afford to miss pay would get understandably upset by this (which is why our booze events rarely happened before 4pm).

    5. Damn it, Hardison!*

      I make it clear to my staff that I’m paying whenever we go to lunch or coffee. I call it “manager’s prerogative.” I also make sure they understand that gifts flow down (with the exception of the occasional homemade baked good. I’ve been lucky to work with several good bakers. I’m only human).

    6. Jdc*

      My best ever “meal” with a boss was a very bad day prior. I had messed something up pretty big and on the same day, mid summer, our AC went out so the office was misery. My boss said “let’s go grab lunch”. This was also my first office job. I was sure it was to fire me. We sat down and she said “I just wanted to get out of that heat and I know you’re stressed, let’s work out a plan to fix it”. Patty, you were the best boss ever. I wasn’t the best employee being so young and inexperienced but her kindness and compassion have stayed with me.

    7. The Other Dawn*

      Yes, it helps so much when a new boss spells it out like that.

      I’ve been at my job a year (today, actually!) and came in as the manager of the department. I’ve been a manager for years, so I’m used to the whole “the company/boss is buying lunch” thing, but it hadn’t occurred to me that my team members, who are hourly non-exempt, maybe hadn’t experienced it all that often, if at all. I had a team lunch on site to celebrate a whole bunch of events–basically every person had something to celebrate at that particular time–and people were talking about punching out for lunch. Do they need to make sure they go back to their desk after an hour and punch in? Do they just not do anything and I’ll adjust time sheets? Do they need to punch out for the whole 1.5/2 hours and it’s unpaid? Someone finally asked me and I said of course you’ll be paid as you normally are. Don’t punch out. The team lunch is time worked and you can still take your normal one hour lunch separately or just go home early, that way you still have that same hour for errands, downtime, etc. It never occurred to me they wouldn’t know this, or this hadn’t been done in the past.

  3. (Mr.) Cajun2core*

    If you feel you must and if and only if it was a really nice place and you could (but don’t have to) shoot a *very* quick email later in the day, saying, “Thanks again for lunch. I had never been to XYZ before. The food was great/better than expected/lived up to reputation. What did you think of their ? I loved it.”

    Again, that is optional and only if it was a very nice place.

    1. sacados*

      Agreed, but I also think that’s the sort of thing you would only do fairly infrequently. OP says these lunches happen several times a month, so an email like that might feel a bit overkill if OP sends one every time.

      1. (Mr.) Cajun2core*

        Agreed. I would only send it if it were to someplace “special” or “unique”.

  4. ThisColumnMakesMeGratefulForMyBoss*

    In addition to every thing Alison said, you may want to bring it up as a general “I appreciate all you do” in a one on one or annual review. I wouldn’t bring it up frequently, but maybe once or twice a year just to let her know that the way she treats you isn’t going unnoticed.

    1. Mediamaven*

      I agree with this! There’s nothing as a boss like feeling like you are doing something right. I think a holiday card is a nice time to say it.

    2. Washi*

      I agree with this. I think if the lunches make you feel nice, the best way to return the favor (if so inclined) is to voice your appreciation to your boss every once in a while. Something as simple as “I’ve learned a lot about X from you” or “Wow, I’ve never thought about Y that way before, this has been really helpful” would probably be very gratifying.

    3. Not a Dr*

      I am on this train! And if you wanted to do a card/note, do it once with “thanks for making this place a great place to work, I really enjoy the time I spend here” or something that feels right to you. And do it on a signifigant day. Your work anniversary, a holiday, I have seen some people use thanksgiving as an excuse for giving thank you notes, etc.

  5. Pay No Attention To The Man Behind The Curtain*

    If there is ever an opportunity to pick up coffee for her or pick up on a small take out order when you are already out picking up your own (just pick up — not pay for the boss), it might make you feel more like your reciprocating. But because of the power difference, you don’t need to reciprocate anywhere near the same level (like she buys lunch a few times a month, you share your coffee creamer or a granola bar when she’s in a spot).

    1. Annie Nymous*

      Excellent idea. I used to do the, “Hey, I’m running over to X, do you want anything?” with my old boss.

    2. LW*

      I’m the LW. This is a great suggestion, especially because I naturally do this already. I’ll (very) occasionally pick up breakfast for the office in the spur of the moment or (more often) bring in something sweet I made and make sure to save a nice looking one for the boss.

    1. HS Teacher*

      Yes. In the early days of my corporate career, I instantly bonded with a boss who enjoyed taking me to lunch. We were both fans of the same types of things and really enjoyed each other’s company. I was way too green to realize the optics of it weren’t that great.

      When I found out the things some of my coworkers were saying about me I became really angry. There were rumors of an affair, and my coworkers were less than pleased at the preferential treatment I was getting, so there were consequences I hadn’t anticipated.

    2. Smithy*

      I think in a positive working environment and management structure, there should be no extensive jealousy/resentment. I think that reaction is most likely to emerge when there are clear patterns of favoritism and a less professional structure overall. If there’s a legitimate perception that the “friends” of the boss get better assignments, shifts, etc. then that’s a broader problem.

      If it’s a situation where the boss is taking you to lunch at places considerably beyond the standard price range of most of your colleagues on a regular basis than being a bit more modest in your selection could help. But I do think that jealous around lunch with the boss is most common when there are larger issues of favoritism at play.

      I used to be the only fundraiser at a local nonprofit outside the US. The salaries of all our staff were considerably smaller than our European or North American donors, and as the only fundraiser – I was the one who regularly would be taken out to meals by them, sometimes at places much fancier than we could afford regularly. I worked with one woman who made it very clear she thought I was getting some incredible perk denied to the rest of staff, but it was so outside the norm she got two very strongly worded conversations about professional norms in our industry that it ultimately shut it down.

    3. LW*

      LW here. I don’t see this as an issue. We’re a small professional firm, and I’m the only professional employee (everybody else but me and the boss are admin), so we are the only ones out of the office ever. And I’ve never mentioned it in front of the other employees, so I doubt they even know.

      She does bring a catered lunch in for everybody every so often, though, and (maybe out of a sense of fairness?) I always just sit on the sidelines when the others are choosing restaurants to order from.

  6. James*

    I’m wondering if the boss paid for it, or if the company/some client paid for it. The office I work in has, as a coworker put it, a low threshold for free food. And meeting with a colleague to chat about work counts as a business lunch, especially if you’re on a firm fixed price project with a healthy margin. And a good boss can learn a LOT by random chats with employees, even if you’re being perfectly professional and never discuss work.

    1. Goliath Corp.*

      Yeah my immediate thought was that if the boss is paying, she’s expensing it. A quick thanks is all that’s required.

      1. What we've got here is failure to communicate*

        It would be great if more people would acknowledge that they’re expensing things, especially with people lower on the food chain or who are newer to the company. It’s hard to pick up on what’s ok to expense from your company’s perspective if no one mentions they’re doing it or talks about where the line is.

        1. Goliath Corp.*

          Oh 100%. I hate that the people who make the most money know what they can expense*, whereas people at the bottom of the food chain are always shelling out their own money. I make a point to pass along what I know they can expense because I hate that the lack of clarity disadvantages them (us).

          *I understand that execs will be expensing more on dinners and such because it’s part of their business to be wining and dining people. But it grinds my gears that the junior staff aren’t made aware that they can expense things like cabs after late-night events.

    2. LW*

      It’s a sole proprietorship. The money I think is expensed technically but is ultimately coming out of the boss’s pocket.

  7. Nee Attitude*

    A former boss invited me to lunch to “celebrate my new position”, only to try to force me to reveal information about my coworkers. When I made it clear that I was not going to, he got up and left the table, leaving me to pay the tab.

  8. yup yup*

    My first Real Job after college started after a summer of temping and living on the edge. I literally had two dollars to my name on my first day of work. Three of us started the same day, and to my horror, our new boss suggested we go out to lunch. She was pretty young herself and didn’t pick up the tab. I (I guess fortunately?) didn’t expect her to, so I ordered a piece of garlic bread for $1.95 and a glass of water, and then spent my very long walk home (no bus fare!!!) lamenting the fact that my new colleagues thought I didn’t know how to tip.

      1. yup yup*

        I walked or got rides to work, and I guess I ate food we had in the house. I lived with a bunch of roommates, I imagine maybe one of them spotted me a few bucks? I don’t really recall. I do know that I didn’t have any credit cards or any safety net whatsoever… lived mighty close to the bone back then!

        1. Artemesia*

          Yeah my first job was as a teacher and I started around the first of September and didn’t get my first check until the first of October. Some near starvation was involved.

          1. Western Rover*

            Wow, the two times that I’ve had a job that paid me monthly, they each gave me a healthy advance the first day without me even asking. But neither of them was a government job.

    1. Garlicky*

      Poor you. I like to think experiences like these build character (& empathy for others).

      OP, paying your lovely boss’ generosity forward, now or in the future, also works.

  9. Mediamaven*

    Totally unrelated but I’ve had old employees come visit and want to grab lunch or drinks. They still expect me to pay for it, and I still feel like I have too. I want to learn how to shake that feeling but likely that won’t happen!

  10. AnotherSarah*

    Excellent and I’d only add one thing–if you’re ever participating in a review, remember that these small gestures (esp. if they add up) count a lot towards “creating a collegial environment at work.” I wouldn’t even say what the gesture was–sounds too much like “Joe would often spring for coffee and so I like him”–but I’d add that little note.

  11. Fikly*

    I would add to Allison’s excellent advice on the topic of how to show gratitude for patterns of small acts of kindness at work.

    Every once in a while, take a moment to say thanks for them in general. People tend to appreciate that these gestures are noticed, and that you have taken the time to call them out for it. Doesn’t have to be public, just a quiet word will do.

  12. LogicalOne*

    My first inclination is to thank your boss/manager for lunch and for the time invested and especially if they pay for the meal. I would feel really good that they want to spend lunch with me and are willing to pay. It really means they value you as an employee. Now does that mean kissing butt to your boss at every opportunity? I don’t think you should have to. But overall, I think just a sincere ‘Thank you’ or a reiteration of a Thank you would mean a lot to your boss. Appreciation is always welcomed.

  13. Master Bean Counter*

    A simple thank you at the time is all that is necessary.
    If you go out to lunch with a higher up, always assume they are buying until you hear the words “Separate checks please.”
    Please don’t argue with them about buying a simple, “I was going to get my own.” is all the argument the boss wants to hear.
    If the boss say’s let’s go I’m buying. Say nothing but thank you.

  14. CookieWookiee*

    OP, if you can, maybe making/buying a shareable treat your boss has mentioned she likes? Edibles are (usually, in my experience) a fairly casual, but welcome, way to say thank you in an office environment. You could bring it to her office first, then put it out for the rest of the office to enjoy.

    Warning tho, this will likely run afoul of Allison’s sensible “gift down, not up” rule, but if you felt you :really: needed to do :something: (which I totally get, btw), it might be an option.

    1. wendelenn*

      In certain states, where certain things are legal, “Edibles” might just mean something different!

      1. CookieWookiee*

        Hahaha you’re right, that didn’t occur to me. Obviously not THOSE edibles, not at work at least.

  15. Sal*

    Affair – You did the right thing by telling management and keeping a cool head. What you definitely don’t want to do is lose your temper and slash his tires, or wait for him after work and introduce his face to the concrete.

  16. rudster*

    Wait – who is paying the other half of the time? I assume they are splitting the checks on those occasions. Then the boss isn’t being all that generous, since on those occasions she is giving LW an invitation she can’t refuse, or would feel pressure not to refuse, to essentially spend money on lunch out half the time, when the LW might that a financial burden or simply have other plans. If the boss is inviting, it’s basically a business lunch, and the boss should be paying.

    1. LW*

      I’m LW. I do actually say no to lunch occasionally. Unless theres a pressing business reason we have to get lunch together (in which case she always pays), the invitation is always framed like, “were you thinking of getting lunch around here, or did you have other plans around the office?” It’s very casual, and if I decline, we’ll usually still go to pick something up for her, so I don’t feel any pressure about it.

      Thinking about how easy it all is really makes me aware of how happy I am to work where I do.

  17. Enginear*

    Whenever I’ve had my boss or grandboss take us out for lunch, I just thank them for lunch and go on with my day.

  18. Me too!*

    Same thing happened to me at my current job! I was so confused at first why my boss almost always paid for my lunch, then I realized it was partly of her way of thanking me for my work and also not taking advantage of the power imbalance between us. I always say thank you and channel my gratitude in other ways, like helping surprise her when she gets an accomplishment. I’ve also occasionally paid for lunch on special days (like her birthday). A little seriously goes a long way!

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