do I need to report a work tryst to HR, am I the Halloween Grinch, and more

It’s five answers to five questions. Here we go…

1. Do I need to tell HR I slept with a coworker?

I work for a very, VERY liberal company that counts many couples in its ranks (though nobody in anyone’s reporting structure are together — that is a solid no and we have really great HR).

Recently, at a work conference, I slept with one of my colleagues from a different division of the company. Our divisions do zero work together, are totally separate income streams/client bases/etc. and work out of offices in totally different cities. I am in my mid 40s and more senior in my career than he is, as well as reasonably well-known/high-profile in our industry. He is around 30 and is pretty advanced in his role due to a long tenure at the company, though is not known in our industry due to his role. If it matters, I am a woman and he is a man.

Is there any reason I need to report that this happened to HR? There is no policy it would violate, but is there something I am not thinking of where it could benefit me to have on the record that this consensual event occurred? I have no influence over his career at all, though I am friendly with his boss (just from being around for a long time in the same circles).

This is also not an issue in my marriage, as my husband and I have allowances for these things. So I’m not worried about this information getting out to anyone in particular. I also don’t think anyone saw us leave together (and given the extremely liberal/casual/friendly nature of our company, I think one of my colleagues would have made some sort of comment to me about it if they had).

I am not making the argument that my company culture is good or that my style of marriage is for everyone! I’m just wondering whether, given all this, is there a reason to report this that I’m not thinking of? For what it’s worth, the event after which this happened was pretty wild and I can’t imagine we were the only folks who behaved in this way! It’s just the age gap and seniority gap that makes me wonder if I should say something.

You do not need to report it to HR.

It would be HR’s business if you were in his chain of command or were being considered for a position where you’d have influence over his career, but neither of those are the case.

You had a private, consensual adult encounter that doesn’t sound like it will intersect with your jobs at all, and you can keep it private.

2. I don’t want to be a Halloween Grinch

A few years ago, I had a traumatic brain injury on Halloween. Whatever you’re picturing when you read the phrase “traumatic brain injury” is almost certainly a lot more dramatic than my reality, but it has left me with some long term neurological effects that I’m still trying to (physically and mentally) heal from. The main one is I’m now sensitive to bright / flashing lights.

I’m sure there’s no good day for a difficult anniversary and Halloween is a particularly rough day for me now. Even if I somehow forgot what day it is, it’s something I would see or hear about. As the seasons change, I see more and more light decorations outside homes and strobe lighting is a popular addition to haunted houses. People have asked me how I got injured on Halloween expecting a fun story, seeming to forget that all the regular ways to get injured still exist on October 31.

Right now I’m in a place where Halloween bothers me a lot more than it probably should. Last year at work, someone decorated the kitchen and while it was mostly cute (cobwebs and cartoon skeletons etc), there were some horror decorations that made me want to avoid the room altogether. My personal preference would be to use a coffee machine that isn’t decorated with blood splatters and a decapitated head, but nobody else seems to have an issue with it. Do you have any tips on how to survive an uncomfortable celebration without being a Grinch?

Talk to whoever in your office coordinates this kind of thing now, before decorations are going up. Say this: “If there will be Halloween decorations this year, could we keep it to things like cobwebs and pumpkins? Last year there was a lot of gore with blood. It’s rough for me because I had a serious injury on Halloween, and I wouldn’t be surprised if there others who are sensitive to gore too.”

That last part is true — there are a lot of people who don’t want to deal with macabre imagery at work (or at all).

Related:
I had a panic attack over a Halloween decoration at work
my coworker goes overboard with grisly Halloween decorations

3. Can an employer say telework is never allowed as an ADA accommodation?

A friend is applying for ADA accommodations at work. Part of their request was the ability to telework occasionally when their symptoms flared. They were told by HR that telework is never allowed as an accommodation, and that if they needed to go home or stay home, they would need to use paid time off.

The entirety of this organization’s full-time staff works hybrid, or is at least eligible to do so. This person’s job is part-time and so it’s not eligible for telework under the current policy, but people doing substantially similar work are regularly working from home. At least one other employee is teleworking as an ADA accommodation, so it was false for them to say it’s never allowed in the organization.

Can an organization rule out something that would fit the definition of a reasonable accommodation like that? I understand that they would need to determine if it is reasonable given any particular circumstance, but it sounds illegal to say it’s never allowed as an accommodation when it’s so visibly allowed as a regular policy.

Yeah, that’s illegal.

An employer could say that they never offer telework as an accommodation if all their jobs clearly have to be done on-site — a grocery store, for example, or hotel. (Although even then, they might have some jobs where they’d need to offer it, like for the bookkeeper.) But for a staff where people are already working hybrid? They’re not saying “we don’t offer remote work, ever”; they’re saying “we don’t offer remote work specifically as a medical accommodation” — and that’s not legal. In order to legally justify refusing to consider telework, they’d need to show that allowing it would be an undue hardship on them, and it’s clearly not if multiple people are doing it in the normal course of business. (Of course, it’s possible that it would genuinely be a hardship for your friend’s particular job, but that doesn’t sound like what they’re saying.)

They could say something like, “Remote work isn’t our go-to first solution for medical accommodations; we try to find other solutions that would work if we can.” But they can’t legally take it off the table completely.

4. Are the vibes bad for everyone right now?

I live in a bubble where everyone I know works in tech or tangentially related to tech, and everyone seems sort of miserable, with the constant layoffs, the demise of seemingly stable SaaS darlings, inflation making the same salary worth less, and the fundamental changes of our jobs related to AI. (In fact the closer they are to AI, the more miserable they seem to be.) Is everyone else feeling this way or am I just living in the self-referential echo chamber of coastal tech?

I don’t think everyone is feeling that way, but just based on the general tone in my inbox I’d say a lot of people are feeling that way. You’re far from alone — this is a bad job market combined with a sense that we’re teetering on the brink of really significant changes that will affect our lives (work lives and otherwise) in very difficult ways.

My inbox in 2008-2009 was gloomy, but right now has an additional sense of systemic instability, and a feeling that we’re living through a more fundamental rupture.

5. How to explain a “backward” career move while interviewing

I was laid off from my senior manager-level role in 2025 shortly before giving birth. Between the horrible job market and my self-funded maternity leave, it took nearly a year, hundreds of applications, and several final round interviews to get just one offer: an independent contributor role with a significant drop in title, pay, and responsibilities. I took it for the excellent work/life balance and because, frankly, I needed a job.

I’m starting to look for new opportunities. Before this, I was angling for a promotion to director. That may be too ambitious now given the circumstances, but ideally my next role would put me back within arm’s reach.

However, recruiters always ask about my current title and the underlying question seems to be why I took a step down. I’ve purposely taken on a lot of strategic work that’s more aligned with my prior level and I make a big effort to highlight it, but the job title and level are conspicuous. (Any attempt to embellish the job title would get caught immediately on a reference check, but I am building a case to request a title change/bump at my annual review and I think my chances are good!)

Do you have any suggestions for explaining a “backward” career move without giving too much away? Or is the job market so universally bad that I’m overthinking this and I can basically just say, “The economy, am I right?” (For obvious reasons, I don’t want to mention that I have a small child.)

I do think you might as well just cite the economy rather than making up something that isn’t true. I mean, you could talk about what drew you to this job and what you like about it, but they’re still going to be left wanting to know why you took a step backwards (largely because they’ll be trying to figure out how you see your career path, what drives you, and how this new job fits in with that).

I’d say it this way: “Well, honestly it was mostly the economy at the time! But I was interested in this particular role because ___.” That way it’s not just “the money and literally nothing else” but you still get the point across.

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