my boss has a bunch of swimsuit photos on the company laptop

A reader writes:

While transferring documents from the company laptop, I found a folder containing photos taken on a cruise my boss went on with friends. While there wasn’t anything particularly lewd, there were a lot of shirtless men, half-naked men in bed, and my half-naked boss with half-naked men in bed (my boss and his friends are all gay). I assume he transferred these from his camera and forgot to delete them off of the laptop.

My boyfriend and I have differing opinions on how to go about this: I think I should delete them myself without saying a word, my boyfriend thinks I shouldn’t delete them without permission because they might be his only copy.

Obviously, there’s also the option of leaving them there and minding my own business, but the laptop is about to get upgraded and we will have to mail in the old laptop to Corporate next month once we get the new one — I don’t know if the discovery of these photos might mean trouble for him or simply joke fodder for the IT crew. Should I do something, or is it not that serious?

Assuming that “half naked” refers to the top half, this doesn’t sound too terribly shocking. Your boss and his friends sound like they’re in swimsuits, or the equivalent of that. Which makes sense on a vacation.

I agree with your boyfriend that you shouldn’t delete the pictures without permission. Why not just treat this the way you would any other vacation photos and tell him? “Hey, it looks like you still have some vacation photos on here, and I thought you’d want to transfer them before we mail this in next month.”

Giving him a heads-up that they’re there would be kind whether or not these are his only copies, since most of us wouldn’t be thrilled to have photos of ourselves in swimsuits shared among our colleagues.

Read an update to this letter here.

{ 94 comments… read them below }

  1. The IT Manager*

    Half-naked in bed doesn’t sound like standard vacation photos to me, but other than that the advice is good since it doesn’t sound like actual porn (for which it would be less ackward to pretend you never saw it and delete without mentioning it).

    1. Ask a Manager* Post author

      The test I applied was that I can easily imagine myself and a bunch of friends being silly and taking similar photos on vacation (swimsuits, a bunch of us piled on to a bed) — especially a decade ago, when we were less staid — and there would be nothing lewd about that. So if it’s okay for a group of ladies…

      1. MentalEngineer*

        Full disclosure: I’m the OP’s boyfriend.

        The example you cite is innocent – unless you were a publicly out lesbian, analogous to OP’s boss. In that case, to someone who just knows that you’re gay but doesn’t know that these are platonic friends, photos taken in bed may take on a tone that, while not overtly sexual, could be seen as risque and/or unprofessional.

        Or, to remove the question of anti-homosexual stigma entirely, just imagine that these are pictures of you in bed, in a state of dishabille (thank you Jamie) with multiple men. No matter how innocent the photos are to you, to someone else this may not be innocuous.

        To me, it’s the possible sexual content that made the photos worth a heads-up. Vacation photos are fine, but some of the pictures in question could probably seem to be more than that (I haven’t seen them).

        1. Ask a Manager* Post author

          Ooooh, I like it when another party to the question weighs in!

          In any case, I’d say that she should give her boss a heads-up regardless of the content of the photos, simply because it’s a kind thing to do.

    2. Jaime B*

      I would agree with you on the “in bed” thing if it wasn’t a cruise. But since it was a cruise, I could see this quite easily. I definitely agree with Alison, just let the Op know and let the guy recover them or delete.

  2. Matt Sofen*

    It depends on the company’s policy. If it says no “suggestive” pictures on the company laptop, then it shouldn’t matter if its men in bathing suits or women.

    1. Ask a Manager* Post author

      That kind of thing is so very much in the eye of the beholder. People commonly have photos of themselves and their family at the beach, etc.

      1. OP*

        It wasn’t really a goofy group photo on the bed, though, I’m talking more under-the-sheets stuff – I have no idea if they were half-naked as opposed to naked-naked, I was just guessing. It’s a picture of a guy covered in a sheet from the waist down, taken by someone in bed with him.

        1. Ask a Manager* Post author

          But they’re on a cruise together, so they’re sleeping in their cabins and hanging out there too. It makes sense that they’re taking pictures in their cabins. That’s not an odd vacation photo in that context.

        2. Ariancita*

          Also, it could be a romantic photo rather than a suggestive one. Maybe one just woke up in the morning and the other took a quick snap. I’ve had that happen. The point is, there is no way to tell if it’s a platonic photo, romantic photo, or something deliberately suggestive (post shag?) photo, so why not give the benefit of the doubt? Why just to the most work-computer inappropriate conclusion? Just let him know, casually, so he can take them off.

          1. Anonymous*

            Even if it was a romantic photo, I’d be so embarrassed if my coworker found a picture like that of my husband, or me, on my computer lol. I would want them to delete it…

  3. Hari*

    I think the only reason for potential drama would be if the company had very strict rules against personal use on computers and it was sent in to IT. However, IT peeps correct me if I’m wrong, to update software on a computer you don’t actually ever need to see the multimedia files on the computer. Unless there was a folder on the desktop blatantly saying “Boss bob in gays gone wild cruise style” I don’t see why they would even find it or ever care to look (unless they were just nosy but I imagine they would have better things to do).

    I’m also thinking if there isn’t some worse photos that were not mentioned here? Besides embarrassment on both parts, more for the boss though, I can’t imagine why OP wouldn’t just mention it. I don’t really see the need for deliberation unless some photos did cross the line into amateur pornography.

    1. Louis*

      Usually IT people don’t look at personnal files but depending on the OS, they might see it with just the preview image (if you have your stuff is on your desktop for example).

      Also if they are installing new software and have some problem because of the amount of space available on your machine, they may will investigate to see what you have on there that is taking all the space… multimedia files are usually the fist thing they look at.

      Another possibility is that they have a process to automaticly scan for pictures, movies and .mp3 if there are company rules against those on company machine.

  4. faltiska*

    You are insisting a lot about the naked aspect, he was naked, there were other naked men, they were in bed and so on.
    You probably have a strong personal opinion about all this but I don’t think it is any of your business to have an opinion about the way he is spending his vacations.
    You should treat the photos like any other vacation photos and let him know he is about to lose them because the laptop needs to be upgraded.

    1. OP*

      My concern regarding this is in no way a judgment regarding the way he chooses to spend his vacations. I just considered deleting them because if a coworker found similar photos of me, I’d rather not know about it. That’s just me, though.

      1. Anonymous*

        I’m like you OP… I’d be really embarrassed and would rather them just be deleted than brought up in conversation lol.

      2. Ariancita*

        Yeah, but if they were innocent photos, would you be embarrassed? You could just say quickly, “Hey Bob, I noticed you left some vacation photos on the laptop. You might want to save them since the laptop is going to be upgraded.” And leave it at that. I don’t see how it’s embarrassing at all. I think it is only because you’re assuming they are sexual in nature. If they were taken on the beach, I doubt you’d have the same concern. It’s only awkward if you make it awkward.

        1. Anonymous*

          My husband and I always go on cruises for our vacations. If he took a romantic picture of me in bed under the sheets, yes I would be embarassed! They are private photos, hence why they shouldn’t be on a company laptop.

          1. Anonymous*

            I agree about the way you suggest approaching it. If it were me, though, I would be really embarrassed at the realization that my private photos were on the computer, lol.

            1. Jamie*

              Yes, but anyone who would be embarrassed by those things wouldn’t have them on the company laptop to begin with – I would think.

            2. Ariancita*

              Sure, then embarrassment = lesson learned. But best to not just delete, because who knows? Maybe the person wasn’t embarrassed, or they were, but still needed to save the photos? No one can know what the other person is thinking; best to just alert them in some innocuous way so they can take action (delete them, move them, be so mortified not to do it again, or shrug it off). :)

              1. fposte*

                Totally agree. I think it’s a mistake to make the goal “avoiding any chance of embarrassing him” rather than “avoiding any chance of his getting a copy of the picture.” He might not be embarrassed at all but really want the pictures, and it’s not the end of the world if he’s a little embarrassed anyway.

  5. perrik*

    Let’s re-phrase the question.

    “While transferring documents from the company laptop, I found a folder containing photos taken at a visit to a dog park by my boss and his Labrador Retriever. While there wasn’t anything particularly scatological, there were a lot of romping dogs, dogs half-asleep, and my boss’s dog trying to hump a park bench. I assume he transferred these from his camera and forgot to delete them off of the laptop.

    My boyfriend and I have differing opinions on how to go about this: I think I should delete them myself without saying a word, my boyfriend thinks I shouldn’t delete them without permission because they might be his only copy.”

    OP, would your answer be any different?

    Personal files probably shouldn’t be on company computers – I’d just remind the boss that Corporate is going to wipe the drives on these laptops without backing them up, so he’d better save anything personal to a flash drive (and NOT the corporate servers). That goes for vacation photos, baby photos, screenplays in progress, or Twilight fan fiction. Especially the latter.

    1. perrik*

      On second thought, please let IT wipe, disinfect, and crush to fine powder any drives containing Twilight fan fiction.

  6. JT*

    Deleting files of any type without asking, which may be the only copies? If there were viruses or something, sure, but anything else? No way. Especially since it it your boss. What if they are his only copies? Then what?

    What Perrik said is exactly right – remind the boss that the computers will be wiped so he can take anything off he wants.

  7. Mike*

    Being in IT, I can tell you this is completely normal. The stuff we find on laptops (or desktops) ranges widely. Unless you’re working at a company with government level security (or frequent audits for compliance), there’s really no harm here… I’d say this even if the photos were a lot worse.

    The fact is that most people’s work/personal life overlap so much, and technology is a crucial part to both these days. Many times the photos we find ARE the only copy the employee has, and right or wrong from a policy standpoint, these are still people’s memories that are valuable to them. I would absolutely tell him they’re there, no need to be embarrassed yourself if you were tasked with cleaning up the computer. It may make him more cautious with his personal information in the future to avoid potentially losing things valuable to him.

    Every computer we get back does get wiped and reloaded, regardless of the condition or age – it’s best to start off with a clean slate to avoid any issues that may not be obvious.

    As a side note, pictures and documents on laptops are tame compared to what comes back on cell phones – but the same answer applies.

    1. Jamie*

      “As a side note, pictures and documents on laptops are tame compared to what comes back on cell phones – but the same answer applies.”

      Ha! Mike speaks the truth.

    2. OP*

      Thank you! Glad to get some perspective from someone who works in IT — and definitely going to be careful if I ever get a company phone.

  8. Zee*

    Forget what the photos are of…if you deleted them or mentioned you had seen them, couldn’t the boss be angered for snooping?

      1. Anonymous*

        If you weren’t suppose to be looking through his computer this article should be renamed “Should I be fired for looking through my boss’s computer”. Answer- Yes.

        1. OP*

          It’s a shared laptop, and maintaining files on it is part of my job. Doesn’t mean I can’t be worried about the impression it’ll give off.

    1. Ask a Manager* Post author

      It sounds like it’s a shared laptop, and that she wasn’t snooping, so I wouldn’t worry about that. Give a casual heads-on and be done with it.

      1. Zee*

        Granted we don’t have the information here so the OP will have to fill us in.

        If it was a titled folder “Mike’s Vacation Pics,” then I think it’s borderline snooping because it’s a shared computer and the OP has to maintain the files. However, if it was an untitled or vague named folder, then I can see where there was a mistake if the OP felt it might be relative to what they were doing at the moment.

        Does everything have to be transferred or are you picking and choosing what needs to be transferred?

        1. OR*

          If the folder were labeled then OP could easily mention she saw the folder versus that actual pictures.

  9. Anonymous*

    Just go with “Oh, hey just remember to transfer any personal files you may want to keep… I forgot once and it sucked so I just wanted to warn you before you shipped it off!”

  10. Anonymous*

    I actually don’t understand what the problem is. Just tell him he should remove his personal files before turning in the laptop.

  11. fposte*

    I’m going to assume the boss is a reasonable guy, since you haven’t said otherwise. In that case, overfocusing on his embarrassment isn’t necessary–if he’s a little embarrassed, he’ll get over it, because there’s no big deal here. You don’t even have to get into looking at the pictures–you can just say you found a folder that looks like it has vacation stuff in it, and did he want to make copies before you did the usual laptop clean? So I’m voting for “tell him” and “not that serious.”

  12. Mike*

    This is the kind of workplace culture stuff I don’t like. They are just photos. Nothing illegal. Nothing graphic. We are all people. Just say, “Hey I saw your vacation photos. You want them on a flash drive?” Maybe he’ll be embarassed that you saw him without his “professional mask” on and he’ll take you out for a beer and you’ll become best of friends. My point is, there are so many things like this people feel like they have to dance around in the workplace when if we would all just understand “right place right time.” Bring up the photos during the morning meeting. No. Bring them up by the coffee pot when you have a moment. Fine. Maybe I should stay in food service where we can swear and tell dirty jokes back in the kitchen, I don’t know if I can do the office thing much longer . . .

  13. Kimberley*

    Why not transfer them to a thumb drive and leave it on his desk or in his mailbox? That way the photos aren’t lost and you don’t have to bring up a topic that makes you uncomfortable. However I think Alison’s response is the best – just ask him.

  14. S*

    Ok am I the only one who thought by teh title of the thread it would be something along the lines of sexual harrassment (by having lewd/suggestive material in the workplace)? and forgive me but I’m slightly annoyed by reading the OP’s question…..what gives you the right to even think you could delete anything personal???? I’m assuming they’re not that lewd or pornographic in nature..just bring it up casually and stop making such a big deal about it.

          1. fposte*

            Dear Alison: I’ve never thought these letters were real, but then one day at the Chocolate Teapot factory my handsome co-worker and I were in the tempering room when…

              1. TL*

                She was young and new to the business world, a bit unsure as she found her way to the new CEO’s office, breathless from the long walk. A tall, handsome man stood at the window, his eyes gazing off into the distance. As she politely knocked and entered, he pushed a hand through his unruly hair, and looked straight at her. Their eyes locked upon each other and she felt a thrill course through her as he said… “Is it legal?”

                1. Neeta*

                  As an avid fanfiction devourer, I’d definitely be interested in this.
                  Brillian by the way (50 Shades of Pay… as well as the is it legal … hehe!).

    1. Anon*

      If it’s company property and a shared laptop then OP or anyone else has every right to delete personal things on the laptop. I’ve heard of people being fired and locked off their computers immediately – I’m sure they had personal stuff there that IT deleted when they re-imaged company property.

      Heck, I had a computer die on me at work and I lost personal stuff. I think anyone who puts personal things on a company computer can’t expect them to be sacred.

      Now is it the decent human thing to do? Of course not. But I can see were the OP may have felt it would save them AND the boss some embarrassment to just delete the photos since they likely would have been deleted during a laptop re-image anyway.

      Just saying if it’s company property – your rights to personal files fly out the window.

        1. Anon*

          I agree it’s not sensible or reasonable to delete personal information.

          What got me is the poster’s sentence: “what gives you the right to even think you could delete anything personal????”

          I don’t think the OP should be lambasted as if it’s illegal to delete personal property from a company computer.

  15. A Bug!*

    I get the feeling that you are making this a bit weirder than you have to. By the wording of your letter, you looked at all the photos in the folder (how else would you know there was nothing ‘particularly lewd’ in there?).

    If so, was that really necessary? If I opened a folder and saw that it was full of clearly-personal image files, then as soon as I’d identified the owner of the photographs, I’d close the folder and give the owner a heads-up about their presence so the owner could deal with them appropriately.

    This isn’t intended to be a harsh judgment on your choice to look at the photos, because we’re all human, and when it does come down to it your boss shouldn’t really have left them there. But is it possible that maybe some of your discomfort with the situation stems from the fact that you did look at more pictures than you strictly needed to in order to deal with them professionally?

    The lure of an open journal, so to speak, can be awfully strong, but I know at least for me, if I submit to such temptation I feel dirty afterward, not because of what I learned but because of how I learned it.

    Anyway, I agree with the majority of the advice here. Just give your boss a heads-up. If you’re uncomfortable doing it personally, an anonymous note will work as well. Just a straightforward “I came across some personal stuff of yours on the laptop, just FYI, you’ll lose it for good when it gets returned for replacement” should suffice.

    1. BCW*

      Agreed. Once she saw that they were vacation pictures, and saw one, that should have been the end of it. But it wasn’t. Now I can’t say I wouldn’t be curious too. However, she was snooping, despite what people say. When you see what the contents of the folder are and still feel the need to look at every single one, the only reason you are doing it is to either be nosy or try to get them in trouble.

    2. OP*

      I’m not uncomfortable telling him that, and that’s what I plan to do now that I’ve asked and gotten sensible answers. It’s just that if it were me in those pictures, I’d rather not know that 1) somebody else realized I was stupid enough to not delete them off the company laptop after uploading, 2) somebody else saw pictures of me that I’d rather they never saw. But now that I think about it, he’d probably be less embarrassed about it than I would be.

  16. AG*

    My fiance worked for a guy who turned out to be sketchy in many ways, including having tons of hard-core porn on his work computer (and not at all hidden, my fiance was using the computer with permission and came across the very obviously x-rated files without snooping). Vacation photos? Not a big deal.

  17. BCW*

    I’m not trying to be judgmental, but I have to ask, does his sexuality have anything to do with it? Here’s an example. I’m a straight man. I’m going to Vegas with my buddies this weekend. There may be pictures of us at the pool on there, shirtless drinking beers. If we are lucky, there may be some of attractive girls with us at the pool. Would the OP find that questionable as well? Or is it just because it was a bunch of gay guys that makes it objectionable to you?

    Again, I’m not trying to imply anything, but it does seem like the context is what made it more uncomfortable for the OP, as opposed to the actual content.

    1. Anonymous*

      The OP said she was worried that the pictures would cause trouble for the boss, or make him the subject of a joke. It only sounded like concern to me.

      While you and I may not have an issue with gay people just living their lives, it’s naive to think that there aren’t a lot of people who *do* have an issue with it, who might cause trouble for the boss. I just saw someone who was trying to be sensitive to that.

      1. BCW*

        Yeah, but it seemed that SHE had an issue with it more than just worrying that others will have an issue with it.

        1. Jamie*

          Trust me when I tell you there the IT department that would even find this noteworthy is a rare snowflake.

          If people knew half of what is pulled off of hard drives of employees after they’ve been terminated they would know how high the bar has to be to even raise an eyebrow.

          Weirdest thing I’ve found which can be discussed on a safe for work website is over 2000 pics of Tim McGraw. Now, I appreciate swapping out the old desktop wallpaper as much as the next person – but I can’t think of anyone I love enough enough to need 2000+ pics of them at my immediate disposal at all times.

          Then again I’ve lived my life quite happily without one pic of Tim McGraw in any media format – so what do I know?

      2. OP*

        Thank you, that’s exactly it. I’m not at all bothered by the fact that my boss is gay (I have happily participated in pride marches in the past and am outspoken about LGBT rights, if that counts for anything) — I’m just aware that not everyone is as accepting of it.

        I work closely with my boss and I know his former supervisor treated him unfairly because of his sexual orientation, and I have overheard his colleagues making jokes about eating Chick-Fil-A in front of him. So I probably felt a little bit overprotective in response, and more worried than I ought to have been.

        1. Jamie*

          Are you sure they were joke – they could just be as ignorant as I was until very recently.

          I had heard great things about the food there, and I think we were even talking here at one point about it…I was unaware of their stance on certain things. It wasn’t until we were googling for the menu to try it one night and I came across an article…

          Anyway, after learning some things I opted to spend my dollars elsewhere. And I really hope there is nothing that would make me politically uncomfortable about Baby’s Steak and Lemonade because their fish and chips are really good.

          So, the point is if they were joking as a way to mock him that sucks…but is it possible they were just as misguided as me? I felt like Sherlock did when Watson put it on his blog that SH didn’t know the earth went around the sun…he was just missing some basic information.

          The BBCs Sherlock – I cannot recommend it enough. Why oh why do the British insist on creating some of the most fabulous television ever created and then parse it out three episodes every 18 months? It’s cruel is what it is.

        2. Flynn*

          The disconnect here is that you seem uncomfortable talking to him directly about it. Going by what you say here, he probably considers you supportive/safe, and has no concerns about you stumbling across these pictures, as they aren’t inappropriate except in that they may remind someone that he’s gay *le horror*. Especially considering that you officially are allowed on that computer.

          As such, why would he be embarrassed that you saw them? I can imagine personal embarrassment along the lines of ‘oh god, people saw terrible photos of me and saw what I do in my time off work’ but I wouldn’t care particularly more or less based on what I was doing (with a few extreme exceptions!)

    2. Ask a Manager* Post author

      I do wonder if that’s at all in play here. The OP said the pictures weren’t lewd, but is really hesitant to just give him a heads-up and move on, and I’m not sure why it’s such a big deal.

  18. Work Computers For Work*


    Just curious, as I read your comments one question immediately came to my mind: Why would you ever think it appropriate to put personal and possibly embarrassing pictures from extra-curricular activities (vacation, in this instance) on a company computer?

    My reaction to such an idea is that you do not fully understand that a company computer is just that, a company computer. Once you create a folder of personal pictures on the computer, it, in a way, becomes company property and anyone with access to your computer can see it.

    In your example, you mentioned vacationing with friends in Vegas, drinking beer while shirtless and possibly having the company of some women. There’s nothing wrong with that scenario at all– in fact, I genuinely hope that you enjoy yourself–however, it does NOT belong on a work computer. This is a violation of boundaries between professional and private, and it shows a disregard for company property; not to mention company time, if you are on the clock while putting the pictures on your computer.

    Again, I’m curious as to why you in any form believe that your vacation pictures– innocuous or otherwise– are at all appropriate for a workplace computer used for work such as Word documents, professional emails, Excel spreadsheets, among other work-oriented tasks.

    1. Ask a Manager* Post author

      Eh, at plenty of workplaces no one would care. I don’t care if someone downloads photos from their camera to their work computer to email them to themselves or something.

      Workplaces that treat people like adults won’t care, as long as the photos aren’t lewd or pornographic, which these weren’t.

    2. Jamie*

      In comparison to this post I seem like a free spirit – which hardly ever happens when it comes to this kind of thing as I generally come down on the side of the IT curmudgeon. In fact that should be on my business cards.

      I honestly couldn’t care less about something like this. When my daughter went to prom I copied my phone pics to my computer because my boss wanted to see them.

      I personally don’t see what the big deal is with this – just let him know he has some personal stuff on there he should move if he doesn’t want erased. Done. No different than if they were pics of him and his elderly mother at Sunday brunch or his dog winning first place in a cat show.

      My rule of thumb, and what I tell my end users, nothing on the work computer you’d be embarrassed to pull up in front of me. I don’t snoop (hard to find anything I find less interesting than other people’s vacation photos unless they include animals) but if I run across something in the course of working on a computer I just want everyone to have the underwear zone covered.

      I do think “half naked” is an odd choice of words for what’s described. If my husband is in his underwear and you can see that he’s half naked. If he’s covered or in a swimsuit he just doesn’t have a shirt on. The word choice sounds harsh to me.

      I would hope the OP is reacting the same as if this were her boss with his wife in the same state of dishabille.

        1. Jamie*

          Yay! Use it in a sentence with one co-worker before the end of the day :).

          I did that when someone mentioned épater la bourgeoisie here the other day – I used it when conducting an audit.

          Seriously, the things I do to amuse myself at work.

      1. OP*

        I would hope the OP is reacting the same as if this were her boss with his wife in the same state of dishabille.

        Oh, for sure. Actually seeing the photos didn’t bother me that much (I wouldn’t want to see my boss without his shirt on whether he was gay or straight!) — my worry was over what it could mean for him if these photos were discovered by someone who wasn’t so open-minded, like some of his bosses.

        As for the use of the term “half-naked,” I just preferred that term over “shirtless,” and they weren’t really wearing swimsuits in the pictures.

    3. BCW*

      Maybe you are right. But do you think its wrong for someone to post their baby pictures online? What about if their daughters wedding? I think the problem is you either have to have a problem with anything non-work related or all of it. And I don’t think most people have a problem with certain things like that.

      Plus, lets be honest, many work computers are used for home and work. Just like many work cell phones are used for both. There are limits to what should be done on each that I will admit to. However, if work wants me to be as accessable as many jobs want, they need to cut a bit of slack on what I’m doing.

      1. Colette*

        The OP has said she’s concerned about these particular photos because of the possible reaction from other people. IMO, that’s not really her call (unless she’s pointing the pictures out to those people, which I don’t think she’s doing). Her boss owns the responsibility for other people potentially finding those pictures – he’s the one, I assume, who put them on the computer in the first place. A casual heads up will let him know others can see them, and give him the opportunity to take action if he wants.

    4. Anon*

      Our company doesn’t mind if we have personal photos or music on our computers (we’re not allowed to stream music or videos, so they actually encourage people to have music if they don’t have an iPod and like to listen to music on headphones).

      I have over 350 personal photos on my work computer, but (a) company policy is okay with that–see above, (b) they’re all totally work safe–most don’t even have humans in them, though I guess my son is “topless” in a few of them from a recent vacation, and (c) they’re not my only copies–the “originals” are on my home computer, backed up to an online backup service, and also on Flickr. Which is actually how I get them onto my work computer, downloading them from Flickr. Tedious, but it forces me to choose which ones I want.

      I enjoy having my own photos as my wallpaper and screensaver, instead of Windows defaults. :-)

      I also have personal documents saved on a personal portion of the server, but again, this is allowed, as long as it’s understood that they’re not private from IT, and not guaranteed to be there forever. But if I type up a quick letter to fax to my son’s orthodontist (as I did today), I want to save it in case I end up having to reprint it the next day when they say they didn’t get it and it’s already been recycled, but don’t need to save it in perpetuity. :-)

  19. Elizabeth West*

    He probably downloaded them from his camera and forgot to put them on his flash drive. Just say “I found a folder with some vacation photos. You might want to take them off before they wipe the laptop.” If the OP is casual about it, the boss might be embarrassed a bit but then he can just do it and they can both forget it.

    Re the gay thing: I’d be embarrassed to see half-naked photos of my boss of either gender, whether he/she was gay or straight. I just can’t see my boss mentally in anything but work clothes. Especially my last boss. EW. But I’d feel really bad if I didn’t mention it and the only copies were deleted.

  20. Not So NewReader*

    Hmm. I have to go back to what is at square one. Boss was told not to use the computer for personal use. He chose not to follow this instruction. It’s an act of kindness for OP to mention the personal file on the laptop. Does not matter what is in the file. It’s not supposed to be there. If it were me, I would pretend not to know the full content of the file. “I glanced realized it was not supposed to be on the computer.” I would be careful to make sure no one overheard me tell the boss.
    You will earn points for your discretion/professionalism.

    1. fposte*

      I may have missed it if it was in the comments, but the original post doesn’t say anything about the boss being told not to use the computer for personal use, just that the computer gets checked before it goes back.

      Which still ends up with my largely agreeing with you. But in general, I think the OP is overthinking this one–I don’t really see it as a delicate matter requiring incredible discretion, because I don’t think anybody’s doing anything problematic here, and I actually think the more kid-glovey this gets treated the weirder it’s going to seem to the OP’s boss. The Chick-Fil-A jokers would seem to me to be a red herring, because they’re not going to be involved. Just ask the guy if you can delete his holiday snaps or if he needs a copy–I’m just not seeing anything here to justify tiptoeing.

  21. EricaVee*

    Maybe the OP could say something like “I found a PHOTO of you on this computer, maybe you should check to see if more of your stuff is on it.” That way it seems like she didn’t see a whole lot, and could save him from possible embarrassment. I don’t think it’s totally unreasonable for the OP to tiptoe around this, nor do I sense any homophobia from her.

  22. HR*

    Seems like this discussion is going on for no reason. You can’t pretend to not see his pics and just delete them..that would be much worse than telling him about the pics, they’re not yours to delete. I think you’re just guilty that you snooped through them all. If you told him “hey there’s a personal folder of yours on this computer do you want to grab the files from it before it gets sent off to corporate” its not a big deal. Its the considerate thing to do.

  23. Vantage*

    If its in the policy that no personal pictures should be saved on company devices then they should be addressed as the IT person. Vacation pictures are one thing, half naked pictures are another. Either way, what does the policy say? If he/she is the boss, why aren’t they uploading the pics at home and not at work afterall? Common sense has gone out the window these days. No one wants to see their boss’ or co-worker’s cracks lol.

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