Searching for the back side of the Moebius strip

Posted by Ask a Manager

https://www.askamanager.org/2026/01/breaking-up-with-my-boyfriend-when-i-work-for-his-parents-awkward-elevator-encounter-with-the-ceo-and-more.html

https://www.askamanager.org/?p=30770

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

1. I want to break up with my boyfriend — but I work for his parents

I just graduated from college last spring with a degree in a field that’s rather difficult to find work in. Lucky for me, my boyfriend’s parents happened to own a business in that field and they had a position open that was basically my ideal role (and probably several steps above any entry-level position I would have gotten elsewhere). I saw it as a great career stepping stone and accepted their offer. It has been far from perfect (typical small, family-run business issues), but overall, I’m comfortable with the position and wanted to stay in it for at least a year before moving on to the next great adventure.

Cut to now, nine months in, and I’ve realized I really need to break up with my boyfriend, as soon as possible. My grand decision to work for his parents is feeling pretty stupid (I’ve felt pretty dumb about it for a while now — feeling trapped by this job situation is part of what made me realize we need to break up). My boyfriend and I live together and our lease is not up until July. I’m willing to eat some money and move back in with my parents while paying off my rent, but in order to do that, I need to keep a job.

I’ve started job hunting, but am left with the decision to miserably prolong the breakup until whenever the time comes that I have something lined up, or continuing to work for his parents post-break-up and take whatever fresh hell that arrangement presents me with. They are good people, and I don’t think they would fire me or consciously retaliate in any way, but I still feel that there’s no way it will really function well.

I’m also kicking myself because I’m so close to the one-year mark, I’ve invested a lot of time and energy into this position, and never did I consider what would happen if all of my professional experience was tied up with an ex’s family. Like, what would a reference from them look like for future positions? Again, I think they will wish me well in life, but it would still feel awkward asking them to speak on my behalf to future employers. On that note, if I do leave before the one-year mark, what should I say to future employers about my leaving? All personal drama aside, I think I’ve done well in the position and accomplished a lot. I would hate to leave it off my resume to avoid bringing up my rather poor judgement on accepting the role.

If your boyfriend’s parents are decent people, they should handle this professionally and kindly. It will be awkward, yes, but awkward isn’t the same thing as horrible or insurmountable — and the awkwardness may go away sooner than you think if you make a point of being really professional and hard-working and showing that you’re determined to continue being a good employee and not let the break-up impact your work. (And really, if they’re thoughtful people, it occurred to them that this could happen when they hired you.)

They’d have to be really petty to let this impact the references they give you, and you say they’re not, so I don’t think you have to worry too much about that. You definitely don’t need to leave this job off your resume!

I do agree, though, you should definitely be job searching actively. There’s nothing magical about making it to the one-year mark in a job — nine months is not all that different from 12 months in that regard. It’s still a short-ish stay, but that’s not a big deal for your first job right out of school. (But you do want to make sure that you stay in the next one for at least a couple of years so it doesn’t start to look like a pattern.) You could tell interviewers that you’re looking to leave because it’s a small family-run business and you’ve realized that you’d like to work somewhere more established/with more structure/whatever makes sense for the context. Interviewers will understand that, and you won’t need to get into the boyfriend situation at all.

– 2018

2. I had an awkward elevator encounter with the CEO

I ran into my boss while waiting for the elevator and things went south. Our company is huge, and our CEO is a very important figure. Everyone seems to always be on their best behavior when she comes around the corner. Out of nervousness, after she asked how my day was going, I replied that it was going well, but that “Mondays are always slow and droopy.”

Our CEO is very big on productivity and positivity. She even preaches about the importance of productivity under any circumstance on a weekly basis during our massive company meetings. The look on her face when I said this seemed alarming. She followed my statement by changing the subject to mention the weather. Is this just paranoia brought on my extreme anxiety or did I really just mess up? Our CEO is great at remembering faces and I’m worried that this will affect how she sees me or, worse, she will tell my direct supervisor what I said. Should I be worried? I feel as though I’m the only idiot to have ever said something like this to her. Help!

It wasn’t a great thing to say, but it’s not horrible either. That kind of comment about Mondays isn’t exactly unheard of; I’m sure she’s heard similar things before (and I’m sure you’re not the only one to make an awkward remark to her out of nerves either). I doubt that she was still thinking about this even 10 minutes later, but hey, if she does mention it to your boss, your boss will hopefully tell her that there’s no reason to worry about you (assuming that’s true), so that wouldn’t be the worst thing in the world. Give yourself permission to laugh at what happened and then put it behind you.

– 2018

3. I don’t want to sit next to my wife at work

My wife and I work at the same company, an insurance broking firm — we met through work 10 years ago. We work in the same overall department now, but where there is any crossover with the work each of our teams does, I make sure I assign other people to deal with her, and she does the same vice versa so we keep work and marriage separate. We currently sit at other ends of the office about 30 yards apart so we cannot even hear each other at present.

The problem is that we now have a couple more employees than desks, so are moving to what our boss is calling agile working, i.e. just use whatever desk you can. It will work okay as there are always people off or away on business. My wife and I are okay with it in principle, but we don’t want to get to a situation where the only spare desks are together. Imagine if we have had an argument about something, or if we discuss work and have a disagreement.

So ideally I would like us to have allocated desks so we can stay sat as far apart as possible, but our boss is basically saying no, it’s first come first served to be fair to everyone, and we should just get to the office earlier to ensure we can bag desks far apart. This sounds wrong to me, and I would be grateful if you could suggest how I can maybe take this forward.

Your boss might be more open to it if there happen to be two desks in particularly undesirable locations and you offer to take those two worst ones as your permanent spots, as a trade-off for not having to suffer under this new plan like everyone else will. But if there aren’t two “worst” desks, or if he’s not open to it, then he’s right that all you can do is try to get there a little early to ensure you’re not next to each other. While it’s true that it’s not good for married people to sit next to each other at work — for all sorts of reasons — he’s also right that it might not feel fair to others if you two get permanent spots to store your stuff while they have to scramble for space every day.

– 2018

4. My company says I didn’t return their property on my last day

What can happen if you say you returned all company property after being terminated, but the company says you didn’t? My employer fired me on Monday, asked for my badge, cell, iPad, briefcase, and chargers. I gave them the badge and cell and went to my car to get the chargers, briefcase, and iPad and then left them in the office right inside the door and left. I then received a letter with my final paycheck saying that I told them I was going to my car and never returned.

It’s too late for this now, but ideally you’d want to give the property to an actual person; if you just leave it inside the door, there’s too much chance that it will get misplaced by someone who doesn’t know the context for why it’s there. If you told them you were going to your car to get these items and then just stuck them inside the door and left, and someone moved (or took) the items, I can see why they thought you just took off. And I totally get wanting to get the hell out of there after being fired, but you did kind of play fast and loose with that property, even if you didn’t intend to.

In any case, all you can do is explain what happened. I’d say something like this to them: “The day that I left, January 26, I left two chargers, a briefcase, and an iPad directly inside the front door of the building, right around 2:45 p.m. My understanding was that you wished me to leave after returning this property, which I did. I hope I didn’t misunderstand. In any case, if there are any loose ends still to be tied up, please let me know.”

Also, it’s not clear to me whether they paid you the full amount due in your final check or whether they’re withholding the cost of these items. In most states, they owe you the full amount of your final paycheck either way, unless you signed a written agreement to the contrary.

– 2015

The post breaking up with my boyfriend when I work for his parents, awkward elevator encounter with the CEO, and more appeared first on Ask a Manager.

https://www.askamanager.org/2026/01/breaking-up-with-my-boyfriend-when-i-work-for-his-parents-awkward-elevator-encounter-with-the-ceo-and-more.html

https://www.askamanager.org/?p=30770