should I tell my boss I’ve had a crush on him, business travel with a coworker who doesn’t want to expense anything, and more

I’m on vacation. Here are some past letters that I’m making new again, rather than leaving them to wilt in the archives.

Due to the quantity of updates we have, posts on Tuesday will publish at 11 am, 12:30 pm, 1:30 pm, 2:30, 3:30 pm, 5 pm, and 6 pm (all times Eastern).

1. Should I tell my boss I’ve had a crush on him?

I have been secretly crushing on my boss, and overcompensating by keeping as much of a polite distance from him as possible. We had a really great connection from the beginning, and our working relationship was so good and so efficient that we referred to each other fondly as work wife/husband.

He is visibly puzzled and hurt by my frosty attitude. He asked me if he had done anything to offend me, and I got so flustered that I went into vigorous denial mode, which only made things worse.

In a few weeks time, I’ll be leaving that job for professional reasons, and it’s highly unlikely that our paths will ever cross again. Before I go, should I come clean with him? I cannot stand seeing the pain in his eyes, and I don’t want to leave him thinking that I hate him.

Ooof. I think telling him about the crush will explain what’s been happening, but will make things Really Really Awkward. What about offering up a vaguer explanation? The thing here is to tell him that there is an explanation, and one that’s not about him, but that doesn’t require a full confession of your feelings.

For example, you could say that you’ve been dealing with some difficult stuff in your personal life (true!) and that you’ve realized that it’s affected the way you’ve interacted with him at work, and that you want him to know that it has nothing to do with anything he did and that you’ve hugely valued the relationship, his mentorship, etc.


Read an update to this letter here.

2. I’m doing business travel with a coworker who doesn’t want to expense anything

I recently accepted a secondment that can turn into a permanent role if I do well. Another person, Rey, also moved into a more senior position within the same team, and we report to the same manager, Luke. Five months into the role, Rey has decided that the position isn’t for her, while I’m happy with the move and looking forward to being a permanent member of the team.

Here’s where it gets tricky: Luke is pushing very hard for us to train overseas for a week and Rey is reluctant to go on the trip. She feels it would be a “waste” since she won’t be joining the team permanently and feels burdened by the fact that our manager would be spending $6,000 for the both of us to attend the training. However, Luke has spent a lot of political capital on getting the training approved, not to mention we’ve already put a non-refundable deposit on the training. The other members of the team have already attended so there is no one else we can transfer Rey’s slot to if she tells Luke she doesn’t want to go. (Incidentally, the training is very role-specific, so if she attends the training and goes back to her original position, she wouldn’t be able to use what she’s learned. My understanding is that the other members of the team already accepted a permanent role prior to being sent to the conference, and that this is the only time the conference is being held overseas.)

I am in charge of researching the travel expenses and doing the cost estimates for the trip: flights, hotel rooms, and meals. I initially would chat with her on what the options are to check for her preferences, but her desire to keep things at a low cost out of guilt is absurd! For example, when I sent her a spreadsheet with the cost of the rooms and their distance from the hotel where the training would be held, she asked if we could just book one room and she could sleep on the couch. I balked at this since it would be a week-long trip and we would be traveling 30 hours per way, but she insisted that she was “used to it” and that it wasn’t a big deal. I sent the costs to our manager without including her comments and our manager advised we could take two single rooms, or look into a serviced apartment with two bedrooms.

She also refuses to look into expensing cab fare even though the hotel we eventually picked is 4 km from the conference and it will be 5 degrees out with a chance of snow. Sharing a cab both ways would only cost $12 per day, which falls well within our $20 daily allowance for incidentals.

I have told Rey to talk to Luke and say she doesn’t want to go if she really wants the company to save on costs, but it has been a week and Rey has said nothing. Now she is refusing to expense our meals for our travel days because “we will be fed on the flight”; however, without going into too many details, the 30-hour journey leaves and arrives at odd times, and with layovers this could mean our first meal from the airline would be served at midnight! I can’t come to an agreement with her on what we will expense and worry that asking for cab fare and meals for travel days for myself will look odd since she won’t be requesting the same. I want to speak to Luke about how unreasonable Rey is being. Do you have any suggestions how to frame this? I’m afraid I’m approaching BEC levels with Rey because of how she’s behaving and won’t be able to articulate it well.

Yes, talk to Luke! You should be able to expense normal costs without worrying about how it will look if Rey doesn’t. Say something like this to Luke: “Rey is trying to keep costs really low and doesn’t want to expense meals on travel days or cab fare. She wanted to book a single room for both of us and sleep on the couch. I’m planning to follow our normal guidelines for expenses, and will be expensing meals and cabs. I wanted to mention it to you since it sounds like she may turn in very different expenses than I do, and I didn’t want you to wonder why.”

After that, don’t worry about trying to convince Rey to handle things differently. She’s being silly, but she can handle this however she wants — and you can proceed with handling your own expenses normally. (And it sounds like you’re doing a good job of not letting her craze for cost control push you into things like sharing a room.)


Read an update to this letter here.

My coworkers won’t help me cut expenses

3. Why won’t anyone eat the last cookie?

I work at a small company (~20 people) and occasionally treats get left in the kitchen for everyone to enjoy. People will gladly eat the food all day until we get to the dreaded “last cookie.” No one will eat the last cookie and sometimes someone will even go so far as to cut the last cookie in half and leave the sad little half to languish away on the plate until someone has mercy on it and throws it out a day or two later. Why will no one eat the last cookie?

It happens with donuts too — someone will cut the last donut in half, and the someone will cut the half in half, and so forth.

It’s rooted in politeness — no one wants to take the last of something, in case someone else was hoping to have some and arrives to find none left. At some level, people worry that if they eat the last cookie/donut/piece of cake/whatever, they’ll be conveying, “I am more entitled to enjoy this cookie than whoever might come looking for it after me, and I do not care that I have created cookie scarcity for others.” (They don’t necessarily worry they’ll be conveying this to other people, who may never know that they took the last cookie. It’s more of an internal guilt thing.)


4. My boss was my boyfriend’s mother

I have begun my job hunt once more and am worried about one thing in particular: my last boss. The whole ordeal was a bit unorthodox and I see now that it was a mistake, but she was my long-time boyfriend’s mother and I was hoping to get her to like me better by doing a great job. It ended up being that she would criticize me for not doing a good enough job (largely for things I was supposed to do after hours), and after many failed attempts by my boyfriend and I to talk to her, and the matter only getting more stressful for the both of us, I quit. Admittedly, I did so quite abruptly and was very unprofessional about it, but it had become so personal that it was hard to think on a professional basis. What do I tell interviewers when they ask me about my last job and my last boss? Things such as why I quit, didn’t list my manager as a reference, and how to let them know that the circumstances of leaving this job was only specific to THIS job, and it would not happen under normal circumstances? Especially without sounding like it’s either person’s fault.

Honestly, I’d probably just be straightforward about it and say, “My boss was my boyfriend’s mother, which ended up being a mistake.” I’d avoid getting into the details.


{ 169 comments… read them below }

  1. No last cookies for me!*

    Regarding the cookie question… Growing up I had a stepparent who firmly believed that it was selfish to take the last of something. We would often buy Costco amounts of snacks, and you could be the person that ate the first 19 in the box of 20, no problem. But should you take the twentieth and last one, you would be lectured. I especially got lectured because they didn’t like me and thought my existing was kind of selfish. (I may exaggerate, but not much.) So it is very stressful for me to take the last of something unless it’s, say, pre-established portions and I just happen to be the last in line. Living on my own for awhile helped me with this, since I was the only person in the household and so I knew I wasn’t depriving anyone else of something they wanted, but let’s just say I can relate so well to the people who don’t grab the last cookie.

    1. Charlotte Lucas*

      I grew with the opposite idea: it’s a sin to waste food. Nobody minded if you took the last one, as long as everyone got a chance to have some.

      I often bring in homemade treats, and sometimes there are one or two left over. I’ve found that security and custodial staff aren’t usually involved in these kinds of office treats, but appreciate them just as much as anyone else.

      1. SheLooksFamiliar*

        My parents grew up during the Depression, and wasting food was a sin in our house, too. We had to ask, ‘Anyone want the rest of this meatloaf/last slice of cake/cookie?’ to be polite. If someone did, we’d split it, or play Rock Paper Scissors. If no one wanted the item, it was fair game.

        Also, back when I brought in baked goods for our team, I made sure to wrap up a plate just for our custodial staff. I’d leave them in the coffee room with a note ‘For the Evening Crew with Thanks!’ or something like that. Cookies that have been out all day, getting handled by who knows how many people, aren’t very appetizing.

    2. Another freelancer*

      I had a similar experience growing up and was called selfish and a pig to boot by my parent. There were times when I ate the last cookie and it was the only cookie I ate of the entire batch but because it was the last one I was in the wrong. I was an adult and moved out before I could allow myself to take the last of something. Now I also ask my kids or anyone else who is home if they want to split the last of something.

      1. Another freelancer*

        Also I don’t think everyone who leaves the last of something is doing so out of something learned in childhood but I can see why some may be reluctant to take the last donut or whatever.

    3. Beth*

      My wife and I will sometimes play what we call the Xeno’s Chocolate game — one takes half, the other takes half of what remains, then half of that, until someone (usually me) just eats the last bit.

      This is for fun, of course. Most of the time, I’ll take one for the team, cheerfully ask “Does anyone else want the last cookie/doughnut/chocolate?” and either eat it or give it to anyone who actually replies.

  2. Just Another Cog*

    I didn’t see #3 when it was first published. Alison’s explanation makes a lot of sense for why people cut a hunk of cookie or donut off, but it annoys the hell out of me when that’s done! It’s weird…..just take the whole thing! At least now I understand the psychology behind it.

    1. ghost_cat*

      Given the state of the kitchen in my workplace, I’ve always assumed it was because the person was scared that if they took the last piece, that they might be expected to wash the plate.

    2. Where’s the Orchestra?*

      I will admit to having done the cut a piece – but generally only when being forced to by the “Mandatory Fun Police” because they were unwilling to accept any answers to the negative about not partaking in shared Office Food.

    3. NotTheSameAaron*

      I usually grab the last one, which seems to break the taboo, since someone will usually ask it off of me.

      1. Agnes*

        This is a pet peeve of mine. At a certain point, you are not “generously leaving something for someone else”, you are “refusing to clean up”. Or “pretending what you aren’t eating” (What, all this food for lil ol’ me?), which is annoying, too.

    4. Constance Lloyd*

      I also think people are reluctant to take the last donut when they’ve already had one! I won’t cut something in half unless both halves are spoken for, but I also won’t take the last thing if I can’t be sure everyone has had theirs. If I’m splitting a dozen donuts with my team of six or grabbing the last cookie from a well organized all staff buffet, I’m fine. But if someone drops an unattended plate of cookies in the break room and I’ve already had one, I’m not going to risk being the reason somebody didn’t get any.

    5. SpaceySteph*

      Back like 20some years ago there was this hilarious commercial (for crackers, i think?) where three men approach a table with one last hors d’oeuvre on the plate. Camera zooms to one man, who has a little old lady appear on his shoulder and say “don’t take it, were you raised by wolves?!” Camera zooms to second man, same thing. Camera zooms to third man who has a tiny wolf appear on his shoulder, wolf howls, third man takes the snack, much to the horror of the other 2 men.

      All that to say, it was very common when I was growing up to ingrain in people that its rude to take the last of something and I think a lot of people still carry that with them even though it leads to a lot of weirdness and eventually one tiny, sad piece of a treat nobody will touch and eventually getting thrown out.

      If the donuts are particularly large and/or piled with toppings, some people may only legitimately want half though.

    6. SheLooksFamiliar*

      There used to be a bakery near my office that made whole and half-donuts. People would cut the half-donuts in half, taking one half and leaving the rest behind. I didn’t get it then, and I still don’t. Just take the whole thing!

    7. LunaLena*

      I used to work in an office in the Midwest that was almost 100% staffed by women, so everyone was excessively polite and/or dieting. This office was the first time I got to witness the Donut Cut in Half/Quarters/One-Eighths phenomenon, and the dreaded Last Donut was a common sight there. People would often walk past and peer into the box and say “oh there’s one left… guess we should keep the box around for now.” Since it was a small office, I just started loudly saying “Does anyone want this last donut/piece of donut? No? I’ll take it then” and discarding the box or plate. After a while, when there was just one donut left, people would just bring it to me and ask if I wanted it, so they could just throw the box away already (I always happily took it, so it was win-win).

      This was especially hard for me since I am Asian and was brought up to never eat the last of something if it’s not yours (you’re supposed to leave the last one for the host as their reward for hosting, so they can eat it while cleaning up after everyone else leaves), but people seemed content with this solution.

    8. Monday blues*

      My work place has someone who will always leave the last cracker in the roll, like think a Ritz cracker.
      As the person who regularly cleans the kitchen, it’s infuriating. because no one will throw out the plastic or close the box of food!

  3. Captain dddd-cccc-ddWdd*

    OP2 (Rey doesn’t want to expense anything) – there seems to be quite a lot going on in this letter. Initially I thought it was just guilt at the company paying for this training which she won’t be able to use, causing her to act in these outwardly silly ways.

    I don’t think guilt is quite it though (especially in conjunction with the update, where she refused to share a cab with OP even though sharing a cab doesn’t cost any more than a cab for 1 person which OP was taking regardless). She seems to want to *demonstrate* to OP, and to anyone who observes it, that she’s doing all this to keep costs down. It is an outward facing act, not inward facing as things done out of guilt usually are. It’s like she’s saying OP can incur the cost of a cab but she, Rey, had NO PART in that cost.

    Rey seems to have quite a narrow minded approach about all this. Is there really nothing that can be gained from taking that training, even if it isn’t directly applicable? Presumably the more senior role (that OP is taking permanently but Rey isn’t) is “related” in some way to their existing roles, otherwise it wouldn’t make sense to have multiple people from the same team be seconded there. So even if Rey isn’t directly applying the training, it is probably useful context for working with (or alongside) the secondment team. And Rey might change her mind about the secondment role in the future…

    1. AcademiaNut*

      I suspect it would have been a combination of things. Feeling guilty because she’s not going to use the training, quite possibly mixing with anxiety, issues from childhood, and/or a need to martyr herself in a performative way, leading to going through a complicated system of self-deprivation to make herself feel/look better. Plus maybe a lack of understanding how business expenses work – that paying for a course she won’t use in her job is better than a last minute cancellation after using political capital to set it up, and that the expense of food and transport is minor compared to the cost of airfare and the training.

      Logic isn’t really involved, as insisting on taking a bus while her coworker takes the taxi actually costs the company more than sharing a taxi would.

      1. Observer*

        Logic isn’t really involved,

        Absolutely correct. And once you realize that, when dealing with people like this, it’s very freeing. Because you can stop taking up mental space for dealing with it. Just do your own thing and don’t worry about whether / how much to accommodate them.

    2. Spiders Everywhere*

      Extreme frugality is often a control issue. It sounds like Rey was feeling trapped and turned to obsessing the over the one part of the situation she felt like she had control over as a coping mechanism.

    3. ecnaseener*

      I don’t think the cab thing makes it more likely to be outward-facing – people aren’t always entirely logical in their feelings of “well, the outcome may be the same whether or not I’m there, but I’ll feel better if I don’t participate.”

      1. Snow Globe*

        But it is actually *more* expensive if she takes public transportation rather than joining her co-worker in the cab. I know people aren’t always logical, but that seems so completely obvious I can’t believe she wouldn’t realize it.

    4. Minerva*

      Looking at the update I actually think that there are 2 separate issues at play

      1. Guilt at having the company spend money on her.

      2. Perhaps a natural inclination to…shall we call it frugality? Seems like she went to extreme lengths to save money in general, not just the company’s money.

    5. Momma Bear*

      I think that Rey’s refusal to expense anything is way beyond simply wanting to save the company money. There seems to be a control factor or anxiety at play. I wonder if she grew up very financially insecure and struggled to accept that the company might pay her back on time. I’m glad that ultimately she transferred to another role and hopefully this won’t be as much of a problem for her going forward. Taking public transit is fine, but packing canned goods to avoid asking the company to reimburse her for meals was a little extreme.

    6. learnedthehardway*

      I think that Rey is being silly, but I also don’t think there’s much point to trying to interpret her motivations about it. Rey told the OP that she’s feeling guilty about spending company money for the training because she’s going to go back to her old role. There’s no reason for the OP to interpret that this is anything about her own spending.

      You can tie yourself up in knots wondering if there is a subtext or hidden criticism, when in reality, the person really is only thinking about their own perspective.

      Rey should have realized that she should either tell her manager she didn’t want to / couldn’t go on the training (for whatever reason) OR should have gone to the training, participated fully, and submitted reasonable expenses for doing so. While she might not intend to continue in the functional area, she could have gained valuable insights that would have made her more effective in her future career (eg. someone who wants to be an engineer is going to learn about the sales process if they do sales training. An HR person will learn about what Finance needs by getting some finance training). And she would have built relationships with people.

      1. Ama*

        I do kind of wonder if she’d heard stories about companies that expect you to pay back training costs/tuition if you leave the company before a certain period of time and was afraid that would happen to her if she opted to go back to her old job. Which should have been a conversation with her boss but I also kind of understand why she might have had a hard time essentially telling her boss that she didn’t see herself taking the job permanently.

    7. Artemesia*

      I particularly liked her note that she would sleep on the couch in the OP’s room and ‘I don’t mind’ being totally insensitive to the fact that she is imposing on the OP and her privacy. This is a very odd duck.

  4. Posilutely*

    Number 3: For the first time ever, I wildly disagree with Alison. This happens all the frigging time at my workplace and it is absolutely not rooted in politeness. No-one takes the last biscuit because if they do, they will have to take three steps across the room and either put the plate in the dishwasher (not even wash it up themselves!) or put the packet in the bin! People will even break off half of the last one and eat it so that technically they don’t have to spend 5 seconds of their life sorting out the plate/packet. I actually really love my colleagues but this is my biggest inconsequential annoyance. Fortunately I haven’t ranted at all here so you can’t tell(!)

    1. EllenD*

      I share your annoyance. Although, it is more often that someone one takes the last one, but leaves the package. At a distance, it looked as if there’s more there and you arrive to be disappointed. Anyone can take the last one, so long as everyone else has had the chance to enjoy the treats (at least wait an hour or two). I once told a boss from another team off for taking the last treat from a packet and not putting it in the bin. If someone is kind enough to bring in treats, those benefitting should have the good manners to tidy up and not burden the generous person.

    2. Emmy Noether*

      I think it’s a mix. It also happens at my work, where the expectation is that the person who brought in the things does the cleanup.

      A lot of people are raised to not take the last of anything. In my husband’s family, if you want to take the last, or any seconds, or anything to drink, you *have to* first ask around who else wants some (I actually prefer this to my family of wolves where I had to eat fast for a chance at seconds of the thing I wanted.). This works fine when it’s a family around a dinner table, less fine at work.

      And then there’s the washing/cleaning up thing, which is definitely a factor as well.

      In total, a lot of people just don’t feel right leaving an empty plate of crumbs.

      1. Turquoisecow*

        My husband does this too. If we’re sharing an appetizer or something and there is one left he will always offer to split it. First he asks if I want it, I’ll say no, then he’ll offer to split it, and only after I’ve declined a second time will he eat the damn thing. I figured it was some sort of similar “don’t take the last one unless you’re 100% sure no one else wants it” thing drilled into his head by his parents.

        1. Weaponized Pumpkin*

          I’ve been known to share the last bit of appetizer not because I want it but because it’s easier than continuing the “no, really I don’t want it” dance! (This usually doesn’t happen, i am pretty comfortable saying no but sometimes with semi-strangers it does get weird. For example, first dates where everyone’s trying to be gracious.)

    3. I should really pick a name*

      When I was in the office, people were perfectly comfortable with leaving dirty dishes out.

      That didn’t stop the half doughnut thing from happening.

    4. amoeba*

      Eh. It happens as well when there’s no washing up involved, at least to me! Like, think, a pack of cookies or something.
      I do feel it’s mostly politeness, at least when I’ve encountered it. However, after a bit of a polite dance of “oh no, but only if nobody else is hungry!”, somebody usually is found. So maybe we’re just less polite, haha!

    5. Anon. Scientist*

      I’m at a senior level so I’ll do it. I wait later in the day (and if someone else is there, ask if they want it) and I’ll take the damn thing. I will also take the 2nd half of a donut because certain people will only take half and then we’ll end up with like 4 halves of different types. Which is annoying.

      We also will have work leftovers that won’t get eaten because people don’t know that they’re available, so I try to emphasize that they’re free, particularly for some younger staff who would happily hoover up anything free. But I definitely will finish off the old leftovers if it looks like they’re gouling to just sit until they’re too old even for me (more than a week).

    6. Pescadero*

      This happens all the frigging time at my workplace and never, ever involves any dishes that need to be washed or thing to dispose.

      This is just very, very, very standard cultural behavior in the Midwest – to the point of being common INSIDE the home with only family.

    7. House On The Rock*

      This is a big part of it, I think the other part is people who don’t want to be seen as eating “too much” or who want to prove that they can practice restraint. Back when I worked full time in the office, whenever there were treats and multiple people in the kitchen, someone would invariable make a show about being “good” and “only taking a bite”. This was especially common maybe 15 years ago when diet culture was all the rage (south beach, atkins, weight watchers, etc.) and people thought nothing of commenting on others’ food choices. Perhaps this is a holdover from that?

      1. I Have RBF*

        …whenever there were treats and multiple people in the kitchen, someone would invariable make a show about being “good” and “only taking a bite”.

        I loathe the performative dieting and “restraint” thing that ends up with 6 muffin bottoms (“Oh, I’ll only take the top.”) or 10 half bagels (“I’m on a diet. I’ll only cheat with half.”) or 8 half or quarter donuts (“Oh, no, my diet won’t allow me to eat those, I’ll only take a little.”), all languishing for hours on the plate, because even the diet people don’t want to take someone else’s abandoned half, they want to partition a whole one, assuming that someone else will of course eat it. I would regularly come along in the afternoon after treats in the morning and find a box full of stale halves, quarters, or muffin bottoms only.

        No one takes the abandoned halves or quarters that I have ever seen. I’ve never seen anyone say “Ooooh, someone left a half for me!” They always say, “Oh, I only want half” and break/cut/tear a whole one.

        I am so glad that I no longer work in the office, because performative restraint makes me want to scream. Yes, true, some people only want half, but they should go find another person to make the split with, not just abandon their seconds assuming that someone else, acting as their mother, will come along and eat up after them.

        Yes, this is a pet peeve of mine.

        1. Ellis Bell*

          If for some reason I only wanted half of something, it wouldn’t occur to me to leave my leftovers lying there for someone else to clean up. I’d either ask if someone wanted to split it with me, or I’d cut it at my desk and own the fact I was throwing some of it away. I honestly think it’s rank to cut something up into oblivion and leave the bits lying around for others. It’s subjective obviously, leaving half of a full party cake is still quite tempting to a lot of people, but you don’t leave the scraps of a small single serving. Just no.

    8. SpaceySteph*

      I have never worked in an office where there was an expectation of cleaning up: if it was a reusable dish the person who brought it took care of their own dish, otherwise it was trashed and usually the table where the goodies were was directly next to a trash can but also people left empty boxes around all the time.

      This phenomenon still persisted. It has nothing to do with taking their time to clean up.

    9. Hastily Blessed Fritos*

      Please believe that other people have different upbringings and cultural expectations than you do, and some people genuinely do feel that it’s rude to take the last of something. Not everything stems from malice or laziness.

  5. Earlk*

    The first one is odd to write into a work advice blog about. If her initial intention was to not see him again in a work context seems like a relationship advice forum would’ve been better.

    1. 248_Ballerinas*

      I would never tell a man that I have a crush on him, but since they are no longer boss/employee, why not initiate friendly contact and see what happens? Assuming they are both single, that is.

      1. KateM*

        It also seems to me that it would help against crushes if you didn’t even start to refer “fondly” about people with whom you have good WORK relationship as wife/husband. (Why do I always hear about “work wife/husband”, never “work sister/brother”?)

        1. Audrey Puffins*

          I have a Work Nephew, but he is the CEO’s dog and I am one of several aunties who like to take him out for a poop break or longer

      2. Pierrot*

        Based on the comments under the update, LW commented on the original post that her boss is gay (and she is a woman), so it seemed unlikely that this crush would develop into something more.

        1. Falling Diphthong*

          Thank for this. ^

          Crushes are not limited to people that it would TOTALLY make sense for us to date.

        1. Ellis Bell*

          I’m not the person who said that, but I wouldn’t either. IME guys tend to take expressions of interest way more seriously than I would from them. So, if I express casual interest, like I’m attracted to them, or want to try getting coffee that’s almost seen as committed or obsessed when you still don’t know how it’s going to go. It’s not a hard and fast rule but unless I could gauge their reaction/knew them well, I’d keep it lighter than “I have a crush on you” and tweak it more to “I’d like to go out some time if you’re up for it”.

      3. Gemstones*

        Eh, even if the boss wasn’t gay, I don’t know. LW talked about giving him a goodbye hug and not letting go to the point the boss had to awkwardly dance around the room. From his POV, this would probably be a kind of weird/awkward former employee, not a romantic prospect.

      4. Erin*

        I told a colleague that I had a crush on him after he had left our job. I spent a lot of time discussing it with my therapist – what different outcomes would be if I told him, how would I feel if I continued to harbor the crush and never told him, etc. It was incredibly scary but I’m glad I did it. He moved to another state for his new job and we still keep in touch frequently. Unfortunately I still have a crush on him but I kind of feel better knowing that he knows how I feel?

        All that being said, despite not reporting to him he was senior to me at work and I don’t think I ever would’ve said anything had he not left.

    2. ecnaseener*

      I don’t think it’s weird at all – just because the work relationship is ending, doesn’t mean you stop considering the effect on future references, etc.

      1. bamcheeks*

        It’s also just a weird place to start a relationship from, IMO. I know it’s ~traditional~, but that was partly because the expected hierarchy in a marriage matched the expected hierarchy in a boss-worker relationship. There are a couple of people that I managed in a previous role that I would 100% be friends with if I met them in another context, but as their manager I supported them through Some Stuff whilst concealing my own Some Stuff, and it just feels like a very unbalanced and awkward place to start a friendship from.

    3. Daisy-dog*

      Alison has shared that she used to write relationship advice. She certainly could have not posted the question, but I know she enjoys questions where work and relationships overlap (even if it seems more on the relationship side).

    4. SpaceySteph*

      I kind of agree, because I also read relationship advice columns and from that slant my advice would have been to wait a little while after leaving the job and then reach back out and confess the crush. Unless he’s married/otherwise unavailable, I don’t see any reason not to take a chance once the work context is no longer a factor.

      But then I work in a niche industry with a lot of couples (my husband and I are one of these couples, we met through coworkers who were mutual friends and have always worked in the same industry, sometimes for the same employer)

  6. It's All Elementary*

    Does anyone else find themselves going down a rabbit hole reading these updates by going back to the original post and seeing another interesting post, and another, and another, and another? Someone take away my phone!!

    1. Juicebox Hero*

      When I first discovered this site, I must have had 20 browser tabs open at once as I read an article, then had to hit the linked articles, and the updates, and stuff linked in the comments…

      Luckily it was my slow season or else I might have gotten in trouble.

  7. I should really pick a name*

    #2 makes reference to what “we” will expense, but I don’t get how Rey has any say in what the LW expenses.

    1. Falling Diphthong*

      I think usually you’re expected to make things easy by staying in the same hotel, potentially sharing a rental car, etc.

      1. UKDancer*

        Yeah when I travel with colleagues we usually arrange to stay at the same hotel and try and share taxis where possible just to make things easier in terms of arrangements and not be paying for 3 taxis to the meeting venue where one would do. We sometimes travel together but it can depend if we’re coming from the same place.

        We don’t have to expense exactly the same but I would expect broadly similar figures depending. E.g. if Larry and Moe go to a conference, I’d not expect Larry to spend 3 times as much as Moe.

    2. Captain dddd-cccc-ddWdd*

      OP was worried that if their expenses were “out of step”, that it would look odd or be queried. So she tried to reach agreement with Rey about what they would (each) expense, so that the submissions for OP amd Rey would be broadly in line.

  8. Llama Llama*

    I think people need in general to stop feeling guilty about the expenses you incur to their company while employed. If the company is so ridiculous to send you to a conference 30 hours (!!) away than so be it. Use you per diem and make the best if it. A company will not go broke because you expensed your lunch.

    1. WellRed*

      This exactly. I will absolutely let the company pay my way. I’m also curious about sending people on a 30 hour trip for a mere week of training. But I also think the employer should not have sent Rey for training she couldn’t use as that did cost them more and wasted her time.

      1. JustaTech*

        My boss and I went on a business trip that was a total of 30 hours of travel (at least) for one day of meetings/site visit. (We were supposed to have some meetings on the second day but our contact had a family medical thing, so had to cancel.)

        And our company would not make up their mind about the trip so we had to buy our plane tickets a lot later than I would have liked and they were ~$10,000 each. (Reimbursed, but I had to float mine because I didn’t have a company travel card.)

        So 30 hours of transit for a week of training seems pretty reasonable!

    2. Pastor Petty Labelle*

      Conversely the company will not stay in business if you don’t expense lunch, or say refuse the pizza.

      This letter reminded me of the letter from the person who cut her retirement, health care and was doing crazy things around the office to save money. She was so convinced of her rightness.

      Rey is also doing crazy saving things that don’t reallymake a difference as to how the company views her after deciding not to take the role permanently.

      1. Antilles*

        That letter is linked right beneath it (“my co-workers won’t cut their expenses”). OP would carry heavy equipment for several miles rather than a $10 cab ride, zeroed out her retirement, opted out of health care, refused to submit expenses, and made a show of refusing to have a slice of pizza when the company ordered in lunch.

        The update gets even more wild because the company ended up laying off 40 people to try to balance the budget, but OP still ended with “and I’m still disappointed with my co-workers for taking a slice of pizza rather than planning ahead”. As though the occasional $20 pizza purchase would have had the slightest impact on a company who had to do millions of dollars in layoffs.

    3. Pita Chips*

      This. I remember scheduling some flights at very late or very early hours to keep expenses down. My boss eventually told me to take the most convenient, they weren’t going to ding me for not taking the cheapest.

      1. UKDancer*

        Yeah I had one boss in a previous company who was difficult about that. I had a choice of cheap flight from an airport across town (let’s call it Stansted) or slightly more expensive flight from an airport that was 20 minutes away from my flat (let’s call it City). My boss insisted I book the cheaper flights. The flight out departed so early that it was impossible for me to get there by public transport so they had to pay for a minicab for me from my home to Stansted which was over £100. The flight back landed so late that there was also no public transport and we couldn’t get a minicab. So they had to pay for a hotel which cost £75. So it cost them £175 which ate up any savings made on the cheaper flight.

        My current boss is more sensible and lets me get flights at times that actually work for me even if they’re not the cheapest out there.

      2. Emmy Noether*

        I used to do this kind of thing at my first job because I was so used to doing it for myself as a student with a very limited budget.

    4. Dinwar*

      When I build projects I build in expenses. Sure, if I can rent a car for $40/day instead of $60/day and it does the same job, I’m going to cut the cost that way! But I’ll still hit my margin goals if I rent the $60/day vehicle, I don’t NEED the cheaper one.

      Secondly, while I love having unused expense budget as revenue at the end of the project, I have to justify it. If it’s too high the client starts asking themselves if I screwed them over during the bidding phase. “My employee decided to save money by spending their own on travel” isn’t a sufficient explanation, and in fact could easily get me into hot water legally. There are things I’m required by federal law to budget for. A client asking why I don’t budget for expenses is one thing; an employment lawyer asking me in court is a whole other world of bad.

      If you want to go to the grocery store and buy your per diem’s worth of food on one of my projects, more power to you. I’ve found that the people who do that are also good at planning and executing work efficiently, don’t need a lot of hand-holding, and are good options for recommending for advancement. Not always, but often enough that when someone says they do it I make it a point to watch them a little more closely; no company has enough competent people, and finding a good one is like finding a diamond as a prize in your breakfast cereal!

  9. Percysowner*

    I suspect there is more going on with Rey than just wanting to save the company money. I don’t know what, but the amount of guilt?, control? being frugal? is not usual. I do know that when she suggested sharing a room and having her sleep on the couch that would be a hard no. When she said she was “used to it” I would say “Well, I’m not!”. When you get to the update it gets weirder. Refusing to share a cab doesn’t increase the cost of the ride, at least where I live. Bringing your own food is just odd.

    I hope Rey has found a position where she is more comfortable and where no one suggests she go to any overnight conferences or any that take longer. It certainly doesn’t sound like something she enjoys..

  10. Ole Pammy's Getting What She Wants*

    the last cookie – just start taking it yourself! even if you dont want it. this also drives me crazy, so I just started taking it (not every time, and always after enough time had passed that it was still in the edible/abandoned gray zone). I noticed over time my coworkers became less afraid to do the same.

  11. Hiring Mgr*

    Rey was being weird to say the least, but I do understand why someone who is leaving the company shortly might not be too jazzed about traveling 30 hours (!) for a week long conference they might not find relevant

    1. WellRed*

      It’s ridiculous how they made her go but it’s all the more reason to make it easier on herself rather than more difficult.

      1. Engineer*

        It’s not really clear from the original or its update if Rey ever actually told Luke she didn’t want to go. She was hemming and hawing to the OP, but didn’t speak to her supervisor about her concerns over the role and the conference.

        1. Percysowner*

          OP said she flat out told Rey to tell the boss that she didn’t want to go if the cost bothered her so much. Ray declined. I don’t see that they were forcing Ray to go.

      2. Observer*

        It’s ridiculous how they made her go but it’s all the more reason to make it easier on herself rather than more difficult.

        Exactly. If Rey had decided to go to the other extreme *that* would very easy to understand. I, depending on what she expensed, people would have been sympathetic but totally not questioning why she would do that.

  12. Fishsticks*

    I was born and raised Midwestern, and I am physically incapable of taking the last of anything. I cannot do it. I can try, I can tell myself that no one else even wants the last bite, but my God my upbringing will insist that I leave that last piece.

    This unfortunately results on a lot of wasted leftovers if my husband doesn’t finish them. And lots of water bottles with a tiny bit of water left, or sodas with “just a swallow” left in the can before it’s put back in the fridge.

    1. WellRed*

      So you leave it for others to perform the follow up labor of dumping out and disposing of instead. And least dump the water in a nearby plant.

      1. Pescadero*

        No – Midwesterners will do this even when it means they later have to perform the follow up labor of dumping out and disposing of it themselves anyway.

        1. Fishsticks*

          Yep. The assumption that I am forcing anyone else to throw stuff out is pretty insulting. I throw the stuff that doesn’t end up eaten by someone out on my own. My husband usually finishes the leftovers because he doesn’t have the same issue with eating the last of something that I do.

      2. Fishsticks*

        No, I can get rid of the leftovers/water/etc later. My plants stay nicely watered, for what it’s worth.

    2. Falling Diphthong*

      Social norms! Not here for your logic.
      There are cultures where the polite thing to do as a guest is to clean your plate (to indicate the food is delicious) and cultures where the polite thing to do is to leave some food (indicating that the food was so generous you can’t even finish it). Neither of these has anything to do with the actual deliciousness or plentifulness of the food.

    3. Dr. Rebecca*

      YUP. Midwest nice. You don’t take the last, even if you’re about to faint from hunger.

      I’m rather relieved to now be on the eastern-seaboard, but far enough south that it’s a combo of New England “get what you want before it’s gone” and southern “we made enough for everyone to have leftovers of their leftovers.”

      1. I Have RBF*

        I was raised with “Midwest nice” on one hand, and “eat fast or you won’t get enough” on the other. The latter won out with me. Ending up food insecure and starving cured me of the Midwest nice.

    4. Hot Flash Gordon*

      It’s the Cursed Last Bite in Minnesota. People will continue to cut it in half until they’ve achieved nuclear fission.

      1. Constance Lloyd*

        Haha I live in DC now, but when I was visiting my parents and sisters in MN over the summer, there was at one point a snack tray with one remaining almond, cracker, salami, apple slice, and cheese cube. I guess I’ve lived elsewhere long enough because I was able to laugh and say, “Okay guys, this is ridiculous. Who wants what?” The tray was promptly emptied and washed :)

        1. wordswords*

          Ha, yeah, if I’m with friends or family, I’ll hit the point of “Okay, folks, we’re Zeno’s paradoxing this last brownie. Does anyone else want it or should I take it?” That’s harder in a work break room situation, though, because you don’t have everyone else there to make SURE sure that no one else is going to be upset about missing out.

    5. I should really pick a name*

      Water bottles with a tiny bit of water left? But that’s not a communal item in the first place.
      I’m mildly perplexed.

      1. bamcheeks*

        I thought that, but figured it meant like 1 or 2l bottles of water/soda that you’d pour into a glass to drink, rather than one that you’d drink from directly!

        1. Critical Rolls*

          I wouldn’t find that better than the last cookie thing — in fact, I’ve razzed my spouse plenty of times about leaving food packages in the fridge or pantry that are what I call functionally empty. A quarter of a a glass of soda, three crackers — functionally empty! Just finish it off an put it on the list so I’m not mislead by the presence of the box!

          1. JustaTech*

            I had a coworker who would do that with the lab reagents. His shelf on the fridge was overflowing with media bottles with maybe 5mL of liquid left (like, a tablespoon) going moldy, but he wouldn’t throw them out, he’d just stick new bottles on other people’s shelves.

            He was a very odd duck in a lot of ways (and a very irritating coworker), and I think at least some of it came from not having much as a child.

    6. Generic Name*

      How does this work juxtaposed with the idea that wasting food is a sin? I grew up in the Midwest, and I assumed my aversion to throwing away food came from that. It could also be generational trauma from the Great Depression that my granny lived through during her girlhood.

    7. kiki*

      I am also Midwestern and never would take the last of anything, at least not without asking everyone in the room first. The one time I broke my normal status quo and did take the last cookie, somebody arrived later in the day and was visibly upset that there weren’t any of Joann’s special cookies left to try. So now I’m back to always leaving at least one of everything, just in case somebody appears out of the woodwork hours later.

    8. My Cabbages!*

      I was reading these comments and noting that it was clear who was from the Midwest and who wasn’t.

    9. Hastily Blessed Fritos*

      In my Midwestern upbringing, once something had become leftovers then “it’s a sin to waste food” took over, trumping “don’t take the last of anything”, so that we’d always have clean-out-the-fridge day to finish up the last bit of whatever was there.

      1. Fishsticks*

        Oh yes. Friday was what I used to call “eat at your own risk”, in which we just each ate a little bit of whatever was leftover from throughout the week, each of us combined managing to finish it off without any one person being “the one who took the last of (food)”.

  13. Caz*

    My dad’s partner is *physically incapable* of taking the last of something, and will cut it in half no matter what it is. This recently led to a donut hole being cut in half.

    She will also push the last of something onto other people, to a degree that has absolutely nothing to do with politeness…

    I find her quite difficult to get on with.

  14. HonorBox*

    Something struck me while reading letter 2. When I started my career, I was traveling with my boss. We were in an airport between flights and I went to grab a little snack. I went back to where she was sitting with my food and she asked if I’d used my company card to pay for what I’d purchased. I told her no. I was just hungry and decided that I wanted something to eat. She explained that not only would I be submitting for reimbursement when we got back to the office, going forward I would absolutely be using my company card for expenses like that. I still remember exactly what she said after that. “You’re traveling because the company has asked you to travel. Would you have spent that money for a snack if you were at home? No. So going forward, when you’re required to travel by the company, you will allow the company to pay for things like that.” I’ve shared that instruction with members of my team ever since.

    1. Pastor Petty Labelle*

      That is an amazing boss. yes you would have had to eat meals even if not traveling, but you are traveling and away from home because of the company. The company therefore pays for your food. No need to grocery shop.

    2. Spicy Tuna*

      Way too long of a story to recount here, but I once had to go on a ridiculous trip for work and my boss told me to expense EVERYTHING and not worry about the costs of things. Some bosses are great!

    3. Artemesia*

      That is a perfect attitude. My employer would not allow reimbursement for snacks in travel only for the 3 meals a day and then with rather low limits. Rather than a per diem, you had a dollar limit for each meal. And if you bought a more expensive meal, say in New Orleans where I am certainly not going to dine at McDonalds and only claimed the allowed amount but of course had to submit the receipt for the actual amount, you got hassled about not being allowed a dinner that cost that much. More than once I had to say. ‘I am not asking the organization to pay the receipted amount for the dinner, just the allowed amount, but I am not going to New Orleans and not enjoying a decent meal.’

      they originally didn’t require receipt for dinners costing $25 or less and then everyone started listing their dinner as $25 and they were convinced we were all eating for less and pocketing the difference and required receipts and then started receiving receipts for $50 dinners and having a cow about it even though people were not requesting reimbursement above the allowed amount.

    4. Jennifer Strange*

      Yeah, I just went to a conference for work with a colleague who I don’t think has previously traveled for work. I told her to keep her receipts for snacks and such and turn them in for reimbursement, but she would keep “forgetting” and just say it didn’t matter.

  15. Juicebox Hero*

    I used to have a candy jar with usually peanut butter cups in it – the little individually wrapped ones. When there was only one left in the jar, no one would touch it. It would sit there and languish for up to a week as people bugged me to get more peanut butter cups, but they wouldn’t eat the last one.

    When refilling the jar, I’d set the former last peanut butter cup right on top and it would promptly vanish. Drove me crazy.

    1. Red Reader the Adulting Fairy*

      “It’s not empty, I’m not refilling it.” Either someone will empty it, or you’ll save a lot of money on peanut butter cups.

      1. JustaTech*

        When we were in college my husband (then boyfriend) was the dorm proctor (kind of like an RA) and one of the “jobs” of the dorm proctor was to have a bowl of candy (to make sure that everyone always had a reason to stop by his room, in case they needed to talk to him about something serious, like roommate issues).
        The dorm/school provided the money, but it was up the to students to shop and up to the proctor to put out the candy.

        Whenever he filled up the candy bowl with mixed candy all the “good” candy (chocolate) would disappear in like 2 days, leaving a bowl of Jolly Ranchers that would slowly be whittled down to just the two flavors no one liked (green and purple). People would pester and pester for him to “refill” the candy bowl, but he would say (reasonably) that it wasn’t empty. And if he’d kept filling it back up with “good” candy we’d eat the entire candy budget in the first month of the semester and then whine about no candy for the next three months.
        No one was willing to throw away the Jolly Ranchers, so they sat there like a dare for a couple of weeks until someone would finally eat the last two and the bowl would get refilled.

    2. I Have RBF*

      I have to admit, I’d have said “I will refill the jar when it’s empty.” then stuck to that. Or, more likely, I’d just eat the last one because I love peanut butter cups.

  16. JTA*

    As for OP2 — In a previous job where I occasionally had travels to expense to my employer, I was in a radically different financial situation than my colleagues (think 2-income empty-nesters v. single income with small children at home). I did not have the monthly cash flow to allow me to expense restaurant meals then wait for reimbursement, especially if I had to expense the hotel room, too. I often “needed to call home” or “take a break” at meal times to get something from the vending machine while the rest went out for a meal. When I did go out, I would order frugally and would use the “saving the (non-profit) organization some money” as an excuse.

      1. JTA*

        Yes. Asked many times. Shamed by management for asking such questions and told I needed to plan better. No longer work there. If we know anything from reading AAM, horrible bosses and organizations abound.

      1. UKDancer*

        Reading the original and the update it looks like that company gives people the per diem in advance because it said the update that Rey “returned nearly all of her travel allowance” unspent. So it sounds like they have some money ahead of time.

        Most of the places I’ve worked have allowed people to get an advance ahead of time if they need one. So you can get some money and it’s deducted from the claim you submit. I don’t get one now but when I started out it was really useful to tide me over.

    1. JustaTech*

      That sucks, and it’s a great reason why organizations should have a travel card for people who are going to travel for work.
      Like, I managed to float the insane cost of business class tickets to Europe, but that was because I’m in a two-income household and it was the beginning of the month (and I submitted my reimbursement the second we landed back in the states). But I had a coworker get hit with overdraft fees because no one told her the policy had changed and she was charged directly for a last-minute cross-country ticket.

      It’s not the employees’ job to loan the organization money.

  17. I'm just here for the cats!*

    in regards to #3 although a lot of the time people don’t want to be seen as being the person to eat the last cookie or donut, there can be other explanations.

    For example, I’ve worked with people who had diabetes or blood sugar problems. They would like some of the treats but cannot have a full one. So they would cut the donut into quarters or something.

      1. JustaTech*

        Someone else who only wanted a bite?

        Like, one of my bosses is forever bringing in donuts and expecting everyone to eat them. But they’re a kind of donut I really don’t like, and he offers them right when I am actively not hungry. But sometimes I need to take and eat at least some because otherwise he’ll get all upset (he’s not a great boss), so I’ll take whatever partial donut is in the box to sooth his feelings and not end up having to eat an entire donut I don’t want.

        1. I Have RBF*

          I think you are the only person I’ve ever encountered, even online, who will take someone else’s leftover half.

          1. Emmy Noether*

            I also take leftover halves! My parents would have ripped me a new one if I had cut something in half when there was already a half sitting there. My colleagues seem to have been raised with similar manners, because I’ve never seen multiple halves of the same thing at work. (Come to Germany! We’re not squeamish about other people’s halves!)

  18. NotAManager*

    Reading the update to LW 1 was…alarming. I hope they’re in a better place today, I just remember in the comments they commented that they wanted to call the boss and arrange to meet to apologize in person for the prolonged hug at their send-off being potentially inappropriate and…yeah. Just uncomfortable all around.

    1. Olive*

      It struck me in the update and her follow-up comments that even though she wanted to apologize, she didn’t seem to have any real concern about her behavior. Going from over-friendly to frosty and “I cannot stand seeing the pain in his eyes…” I honestly hope she’s worked on emotional regulation since then, because this all seems like a recipe for more work angst sometime in the future.

      1. NotAManager*

        Yeah, I got the sense that she was suffering from main character syndrome a bit too acutely – some of her descriptions were romance novel-y and she didn’t seem to be too self-aware. Sincerely hoping she’s done some reflection and learning over the past few years.

    2. Red*

      Yeah, even if her boss wasn’t gay, it was dramatically inappropriate and unprofessional. It’s a bit startling how casual LW 1 was about it.

    3. Cyndi*

      It reminds me very much of when I was a teenager and didn’t really know how to express interest in people yet, and would keep going back and trying to redo interactions to get them “right.” I understand the urge but I’ve known better than to act like that, or even admit to wanting to act like that, since high school.

    4. learnedthehardway*

      I suspect the manager was somewhat relieved that the OP1 had resigned, because I doubt her crush was as secret as she thought it was.

      I would have strongly suggested that the OP not mention it, and move on.

      1. Olive*

        He also seemed to be lacking boundaries and professionalism (although I don’t think the LW is 100% a reliable narrator). But he didn’t write in.

  19. Spicy Tuna*

    My mother’s family takes “not taking the last one” to ridiculous extremes. I was having breakfast at my parents’ house last month and my mother cut a raspberry in half to avoid eating the last one. To poke, I cut the half in half. She cut the quarter in half. My father, exasperated at the ridiculata, finally ate the last little smudge of raspberry from the plate.

    Regarding the travel expense agita… companies usually set per diems for this reason. They have done the calculation as to what they can afford so you don’t have to. There is definitely something going on here beyond guilt. I am a person who takes frugality to extremes and I can recognize that Rey is not concerned with the company’s expenses, at least not primarily.

    1. Lily Rowan*

      My mother will generally only take 90% of whatever, but I have no compunction in taking the rest! Especially when what she has left is not enough to be another serving tomorrow, or is the last bit of salad, or whatever.

    2. Distracted Procrastinator*

      My company does a per diem and I really like it. I generally spend about half of what’s allotted and I get the whole amount, so I basically pay myself extra when I watch what I spend. Some of my coworkers enjoy the opportunity to try new foods or eat one or two meals at a more expensive place than they could afford normally. Some are as frugal as Rey and cook their meals in their rooms and take food from the hotel breakfast for lunch. They love getting to pocket the per diem as extra pay.

      It all works out and is fair for everyone. We get the same amount no matter our position in the company (it’s based on the US GSA rates) and it’s our choice how we spend it. The company budgeted it in anyway.

  20. Student*

    OP #3: This “tradition” of leaving one piece left also has strong cultural roots. When I worked in Germany for a bit, it was practically a social law there.

    The key thing to know is that it (usually) constrains the behavior of the people who follow the tradition. It does not apply to other people. Be the cookie hero your office needs, and eat the last one guilt-free. In practice, I’ve found that most people who follow this tradition will be perversely happy that somebody took the last cookie, and that it was not them. A few will likely react differently, but those folks are too constrained by their manners systems to eat the last cookie, so it is unlikely they will actually say anything and very unlikely they’ll remember it for more than an afternoon.

    If you take the last cookie while people are around, you can keep with the spirit of tradition by following this custom:
    “Anyone want the last cookie?”
    Wave the plate around or gesture towards it for emphasis.
    “Nobody? Ok! Guess I’ll be the oaf who ate the last bite.”
    (Choose one as applicable to the situation: “Happy {Important Day} to Person Y!” or “Thanks to X again for bringing cookies!)”
    Then, finally, eat cookie.

    This lets you verbally acknowledge you are making a “social faux pas” in some people’s minds by eating the last bite. It shows a good faith effort to make sure you aren’t snatching it from anybody else by being greedy. Then, you “redeem” the act by rallying a final thank you, or a final celebration call for whatever is going on that you’re sharing food over. Thus, the social contract is complete and the food is eaten. It’s performative, sure, but it gets the job done if you’re otherwise nervous about it.

  21. Pita Chips*

    Rey might be worried that because she is leaving that any reimbursement for expenses will be delayed or not given to her at all. It’s a valid concern, but she should be talking to Luke about it and not make LW1 deal wtih her problem.

  22. Hiring Mgr*

    If the LW in #1 and their boss were both reaching for the last cookie at her goodbye party they could have had a Lady and the Tramp romantic moment

    1. Red*

      Alas, her boss was gay (as per the comments in the original letter) and her update doesn’t make it seem like her boss reciprocated her feelings.

  23. Industry Behemoth*

    OP2’s letter reminded me of a work training class where one attendee already knew the subject. We were all government employees, and his agency had originally registered another person who left in the interim. Maybe if they hadn’t sent somebody, it would’ve affected their training budget for the next year.

    At another former employer I once removed a small charge from my boss’s travel expense report, to get it just under the accounting limit my boss could approve on their own. Then they’d get reimbursed sooner.

    I wish I were kidding about how that employer, a big bureaucratic company, frequently let much larger invoices sit in the accounting system because the executive who needed to approve them for payment just . . . didn’t. And didn’t. And didn’t. Those executives knew that approvals at this level were their responsibility, too.

    1. Bureaucracy Indeed*

      Working for a bureaucracy myself, I always to try to allow for “if it doesn’t make sense to me, I don’t know all the supporting details.” I even add a caveat that I shouldn’t plan on anyone provided me the details.

      It has freed a lot of mind space.

  24. BellyButton*

    Rey’s behavior was so odd. I understand feeling bad that you are leaving and they are spending money on the training and travel, but $12 for a cab ride, $20 for incidentals is such a small amount, and normal meals– it was very extreme.

  25. JaneDough(not)*

    With LW1, I never understood why they didn’t think about testing the waters after they left that job. I mean, yes, the former boss sent a little work their way, but surely that was less important than the opportunity to see whether a solid relationship could grow with someone so much in sync — one can find clients more easily than one can find a romantic partner.

    I don’t recall any reference to either of them being unavailable (married, partnered, a single parent, a live-in carer for a relative, etc.); I feel a little sad that LW1 didn’t give it a shot.

  26. Semi-retired admin*

    I have to at least partly disagree with Allison’s answer on #3. It’s because they don’t want to clean up. Whoever takes the last item should be the one to toss the empty box and clean up the crumbs. Big ask at my former office!

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