I have to read my boss’s emails … including ones about the love nest he’s setting up to cheat on his wife

by Alison Green on February 2, 2021

A reader writes:

This is from a while back and no longer a current concern, but I would be interested in your perspective on how I should have handled it.

As the executive assistant for a very busy VP, one of my responsibilities became inbox management: having full access to the VP’s inbox, sent items, etc. I was responsible for shepherding 350-400 emails daily. Part of this was looking for messages, and also filing.

Here’s the thing: there were … personal … messages in there that I should not have read. But the subject lines started as something relevant, so I would open them to see if they answered whatever challenge I had been set. Often … they did not.

Often they were between my gruff Mad-Men style VP and a direct report (executive level), and the love nest they were setting up that their spouses didn’t know about. Craigslist links, discussing what name would go on a rental agreement to avoid detection, choosing furniture, and move-in-day menus. There was no way these emails could have been anything else: they were having an affair and wanted to keep it secret from their spouses and colleagues.

But they both knew I was in and out of this account all day. They continued sending these messages after giving me access to manage this account. The subject line would still be a work thing, but the conversation would completely shift away from it and on to links for Ikea beds (“but how good are the springs hahahaha”). This could lead to filing issues if I wasn’t reading through the content.

Being fairly naive and eager to please, I chose discretion. I created a folder for the VP called “personal messages” and started dragging them out of my regular hunting grounds (inbox and sent items). I “casually” mentioned a few times to each of them separately that VP had so many emails I often needed to open and read them to see if they needed my action. They didn’t change their approach.

Other messages were just unprofessional in tone, e.g. resignations were often discussed as “no loss,” and I would then choose to draft a respectful yet gruff-in-tone reply and send as though I was the VP from his account. (Apparently I did this well. Affected staff thought he wrote them and were impressed he “had a heart after all.”)

Both were in powerful, high-stress positions and rocky relationships, and have since been let go (at different times, for reasons I can guess but don’t know for certain).

Nobody else at work knows about these emails. I haven’t told a soul except now you. What should I have done at the time?

Why do people do this!? Your boss isn’t the only one, and it’s bizarre.

I think there are four possibilities:

1. They realized you’d see the messages and genuinely didn’t care, because you were “the help” and they didn’t think they should have to alter their behavior to prevent you from being uncomfortable. (Think of other situations where some people will say all sorts of personal and inappropriate things in front of people who they see as just there to wait on them.)

2. They realized you’d see the messages and genuinely didn’t care, because they figured it was part of your your job to be discreet. This might not be that different from #1.

3. They never bothered to think about the fact that you’d see the messages — they thought so little about this aspect of your job or the mechanics of managing an email box that they genuinely didn’t process it. This seems pretty unlikely … but then again, there are people who do far worse on work computers without realizing it can be tracked, so who knows.

4. They realized you’d see the messages and actively enjoyed that. (Ick, sorry.) I think this is less likely than #1 or #2, but it’s not impossible.

As for what you should have done, you tried all the right things! Creating the “personal messages” folder was smart (and should have been a nudge for your boss, had he cared). So was mentioning to each of them that you read all his messages.

The other thing you could have done was to speak more directly to him about it — to say, “As part of my job I need to read all your messages, and I’m running into some really personal emails between you and Jane. Could you use your personal email account for those, or use a subject line that makes it clear they’re personal so I don’t open them?”

But there was a risk to doing that. If your boss was counting on you to maintain the illusion of his affair’s invisibility, would he have retaliated against you in some way, large or small? Maybe not — lots of bosses wouldn’t. But you shouldn’t have to risk that, or even worry about it.

In theory you could have asked someone else, like HR, for help. And that might have gone well, who knows! (If nothing else, they should have been very interested in knowing that he was sleeping with a subordinate, which is a huge area of liability for companies.) But assuming they didn’t fire him outright, you’d then be stuck working for someone who might or might not know that you’d reported him to HR and caused professional problems for him, and it’s very difficult to work for someone when that dynamic is in play — and even more so when you’re his assistant, which is a relationship that requires a high degree of comfort and trust. So while I would have encouraged you to consider doing that if you’d written in when this was happening, I can understand why you didn’t.

In any case, I’m very glad that this is behind you now and the rest of us can enjoy these details. The other staff being impressed that your gruff boss “had a heart after all” because of your ghostwritten messages is gold.

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  1. SMH*

    I’m curious if OP was ever tempted to send these emails to a personal email account of her own and then forward to spouses once you quit. I’m not positive I would have done this but I would have been tempted to do this once I had left the job.

    1. Ask a Manager* Post author

      Eh, not her place. She doesn’t know the relationships involved or what the consequences might be of doing that (to say nothing of the professional consequences to her).

    2. Jack Be Nimble*

      Maybe that’s a fun revenge fantasy, but I think it’s one of those things that work better as a final, triumphant gesture in a movie about getting back at your boss than it would IRL.

    3. Steveo*

      This will 100% be traceable back to the OP and although it seems morally satisfying is going to cause issues for her if she does it.

    4. OrigCassandra*

      Even from an ethical perspective I can understand the desire to disclose. Assuming this is not a situation of voluntary polyamory (which from OP’s account it isn’t), the uninvolved spouses are risking their sexual and financial health, and contributing effort to marriages they may not realize are troubled and spouses they may not realize are cheating.

      I’d want to tell the uninvolved spouses. (Consider that I am recently divorced, however.)

      But the personal and professional costs of telling are liable to be absolutely immense. OP will be the obvious suspect (even should OP email from a burner account and take other sensible precautions), and VP (who sounds like a selfish ass) will probably come down on OP like the proverbial ton of bricks. It’s not an easy call to make.

      As for HR, OP is in the best position to talk to them if there’s explicit company policy against manager-subordinate romances, but that very much doesn’t mean it’ll be an easy conversation or result in a good outcome for OP.

      Another tactic available to OP is blackmail, but I hope it’s obvious that’s not ethically okay.

      1. Ask a Manager* Post author

        I know someone who once strongly considered telling a semi-friend that his partner was cheating on him; she’d heard all about it from someone who was friends with the partner and didn’t realize that she knew the guy at all. She ended up not doing it, but had really agonized over it. Years later, after that relationship had long broken up and the guy was with another woman, it came out that he was physically abusive to her and other partners, especially around anything that could trigger his jealousy. She is very relieved that she didn’t tell him. That’s the kind of thing I meant above about not knowing what the consequences might be. (That’s not to defend cheating, of course! Just saying you never know what’s going on in someone else’s relationship, especially people you only know from work.)

      2. TypityTypeType*

        Hah! When I was an admin, blackmail would definitely have crossed my mind if I’d had a boss like LW’s. Surely there’s a mystery trope in there somewhere: “VP Jonah Bluster never imagined that meek secretary Melanie Doormat was quietly gathering information and making plans.”

        2. TardyTardis*

          There’s a highly satisfying novel called JANE DOE and its heartwarming sequel where such revenge takes place. They are both fun. :)

    5. Ali G*

      Why though? It’s of little gain to the OP to involve themselves in this kind of stuff. Workplace affairs tend to resolve themselves one way or another.

    6. The Original K.*

      IMO the downside far outweighs the upside. The upside is that she might feel like she did the right thing morally, but the downsides to her would almost certainly be termination and difficulty securing a new position – she’d have torched that boss’s reference, and depending on how much clout he has, he might be able to blackball her. If he’s of Alison’s first or second schools of thought, he would be livid that “the help” had interfered in his personal business in this way.

      Not to mention, what if the spouses have tacit “you do your thing and I look the other way” agreements, and she’s just made it that much harder to look the other way?

      1. Maltypass*

        A friend of mine chose to contact the wife of a guy she was having an affair with, (she only discovered late in the relationship that it was an affair), despite everyone’s advice not to, and the wife responded thanks for letting me know but never contact me again. And I think that’s one of the better outcomes in these stories.

        1. Anonymeece*

          I’ve also heard horror stories of the wife/girlfriend lashing out at the person who told them.

          On the whole, if you have a close relationship with a person (say a friend who has a SO that you know is cheating on said friend), then you have an obligation to tell them in a kind, direct way.

          In this case, however, no matter how slimy the actions of the boss were, I can’t see it working out well for OP to have told. As someone mentioned, in a movie, it would make for a very dramatic moment, but real life rarely works out so nicely.

          1. The Original K.*

            I’ve also heard horror stories of the wife/girlfriend lashing out at the person who told them.
            I’ve seen friendships end over this, more than once.

          2. Sc@rlettNZ*

            Yup, that happened to me. A good friend’s partner was cheating on her with the cousin of a girl I rode horses with. I had never met the cousin before but she came for a ride with us one day and was waxing lyrical about her new partner (who turned out to be my friend’s boyfriend). I told the cousin, and my friend. My friend went nuts and it almost cost us our friendship (the cousin and the cheating boyfriend were also not impressed with me lol but I didn’t care about them).

            So, the next time it happened with the same friend, but different boyfriend (she had terrible taste in men) I said nothing. She found out I knew and went nuts at me for not telling her.

            You really can’t win in these situations.

            1. Tired of Covid-and People*

              Those are women in denial. Why would she lash out for you telling her? You were being a good friend, but your friend is immature. Anybody ending a friendship over this wasn’t really a friend in the first place.

            2. allathian*

              Yeah, well, with the second one, did you say something like “I thought it better not to tell given the way you reacted last time”…

              Are you still friends with her? Some people lash out when they get bad news but realize later that they were unreasonable.

              1. Sc@rlettNZ*

                Yup, the second time it happened I told her that the reason I hadn’t mentioned anything was because of her reaction the first time round.

                We eventually drifted apart – I moved overseas and stayed away for more than a decade and that was one of the friendships that didn’t survive. I haven’t seen her for many years but would actually love to catch up with her (if only to see if her taste in men has improved lol).

          3. Chinook*

            Speaking as a wife with a cheating husband, while I would have appreciated the girlfriend contacting me to out my husband, I would also be suspicious of their motives and immediately jump to the conclusion that they want me to realize him from his marital bond or somehow give her my blessing , which would anger me, especially if I did not suspect an affair previously.

            The wife thanking the other woman and asking her not to contact her again truly is the wife acting in the most polite way possible and, in my opinion, truly shows “grace under fire” when being given life changing, negative news.

        2. Tired of Covid-and People*

          Uh, no. Don’t want to look the mistress in the face. It’s not that she didn’t want to know, she already probably knew, but didn’t want to see the woman screwing her husband. Not the same as a friend telling her.

          I don’t get all this reluctance to do a kindness to someone facing one of the worst betrayals possible. Cheaters can cheat with impunity knowing that not even their friends will get involved. Hope it never happens to any of you!

          1. MassMatt*

            “I don’t get all this reluctance to do a kindness to someone facing one of the worst betrayals possible.”

            Because it’s often not seen as a kindness by anyone involved, as many of the experiences shared in this thread shows.

            In this context, the LW is only getting this info because she is privy to the boss’s emails due to being his executive assistant. Yes, it’s dumb for the boss and his… partner? to be having these conversations on company email but that doesn’t change the fact that a major part of LW’s job is maintaining discretion. Short of something criminal, or otherwise dangerous, I’d expect an assistant to keep their mouth shut.

            1. Crooked Bird*

              Let’s face it, no-one’s going to experience it as a kindness in the moment. In the moment, they’re experiencing betrayal. That doesn’t mean it’s not a kindness. Would *you* (any reader reading this) really prefer not to know?

              That’s not to say someone in the LW’s position should do it, though, given the risk to her livelihood.

          2. JB*

            It is not anybody else’s job to monitor your relationship or your spouse, or report back on them to you.

    7. Jennifer*

      I would have done this, at least so the VP’s wife would know. You could do it anonymously and wash your hands of it once you were done. Cheating is also a form of emotional abuse especially since it usually involves lying and gaslighting the innocent party. They are putting their spouses physical, financial, and emotional health at risk and that’s something worth speaking up about.

      1. Reality Check*

        You know what usually happens in situations like that, though? The messenger (in this case OP) gets shot.

      2. Abyssal*

        I’m skeptical that the tipoff could really be anonymous. Once the shit hit the fan, the VP would remember that OP has access to his email tout suite.

        1. Le Sigh*

          Yeah, I think the odds of being able to maintain realistic anonymity are low, the odds the boss would suspect and target LW are high, and … to what end? There are so many ways this would blow up in LW’s face (or anyone in LW’s position) that it just wouldn’t be worth it.

        2. AntsOnMyTable*

          Yep. If you send them an anonymous emailing telling them their partner is cheating the partner will just deny it, more than likely. If you “proof” in the emails well, then, the boss will know who it came from.

      3. Tired of Covid-and People*

        Cheating IS emotional abuse, think of Betty Broderick and how that piece of excrement she was married to denied he was cheating FORYEARS, gaslighting the heck out of her. Everyone in his office knew but her.

        1. Crooked Bird*

          Yes. Too many people act like it’s a teenager having sex when their mom told them not to or something. It’s taking away someone’s control over their own life by continual acts of fundamental fraud. People have given years of their lives & significant sacrifices to spouses whom, if they’d known the truth, they would have left immediately.

        2. tamarack and fireweed*

          In Alison’s comment example, a spouse was cheating on a physically abusive partner.

          Sure, the archetypical cheating is a form of emotional abuse, but real relationships have enough moving parts that I would only advocate involving yourself if you are either invited by the/a wronged party, or see something that means someone is in imminent danger.

          The problem here is one of workplace ickiness and boundary overstepping *towards the LW* caused by inconsiderate upper-management level people.

    8. Mal*

      Why? OP would be involving herself in a situation she has no place in, even if they forced her there at first. The professional hit if anyone found out would be enough and I’m sure they would, considering there’s only one person it could be.

    9. MassMatt*

      This would be fraught with potential fallout for the LW, and for what? The pleasure of playing Church Lady? It sounds like very selective morality to me—appoint yourself enforcer of marital fidelity while violating your own responsibility to hold what you know from this job’s access in confidence.

      Maybe the VP was a great boss, who knows?

      1. Zillah*

        I’ve been cheated on, and when I found out, I was very concerned for what it meant about my health. Thankfully, I ended up being fine, but I would feel absolutely terrible if someone in a similar situation was more unlucky than me and I could have done something that might have spared them from that – for me, that’s very much a moral problem. However, I don’t think that it’s ever my moral responsibility to protect immoral behavior, particularly not just because someone was nice to me.

        Reasonable people can differ, but I don’t think it’s reasonable to accuse people of selective morality because their framework is different from yours.

        1. allathian*

          I would tell a friend if I had conclusive evidence of their partner cheating, even in cases where I’d knowingly risk losing the friendship over it. But in that case it would have to be really obvious, like if I saw my friend’s partner kissing someone else in the street. This is because I know my friends well enough to know for certain none of them are in an open relationship.

          I don’t know any of my coworkers well enough to care about the status of their relationship, so in those cases I wouldn’t interfere even if I had conclusive proof of what I suspected was cheating. This is mainly because my employer never organizes +1 events, so I don’t know most of my coworkers’ spouses by sight, except in cases where both spouses work for us.

          In this particular case it’s really tough, because the job of a PA is different from most other jobs in that in most jobs you don’t get access to your manager’s email account. That said, I doubt this boss was a great boss in other respects either, given the way LW compared him to Mad Men…

        2. MassMatt*

          I’m sorry for what happened to you. But we fundamentally disagree.

          I see a major disconnect here where people are acting with righteous indignation about wanting to punish the boss’s immorality and completely overlooking the fact that the LW is only coming by this info due to her access to the boss’s email.

          Should executive assistants feel free to blab about anything they consider immoral or “icky” (or even just juicy?) they come across in the course of their duties? Executive assistants are not church elders.

          1. TheAG*

            No, but they’re not in the steno pool, either. They’re professionals who deserve to not be exposed to inappropriate communications and have to deal with such questions.

            The fact that Mad Men boss was so lax in an era where that is pretty clearly not the norm makes me think that if she did expose him, too bad, so sad. I’m not saying she *should* for her personal protection, but he offered this information freely in spite of the fact that he knew it was her JOB to read it. And frankly, putting titles that were work related but content that was personal, makes me think he was either a creeper, or messing with her.

            TL/DR: if she “blabbed” about something that shouldn’t have been in work email to begin with, too bad so sad for the boss.

    10. Anon4This*

      From a practical perspective, please be aware that, with cyberthreats, business information theft, and phishing being major infosec risks, some organizations flag all emails that are sent to public domains like gmail, yahoo, etc. Our security office checks to make sure that people are not forwarding client or company information to their personal accounts, multiple/bulk sends are flagged, particularly if they are within a notice period. Big data analytics makes it easy to see who sent what to whom when.

      This is how someone in my organization was caught leaking customer contact information to a friend’s business (and was obviously fired).

      1. TardyTardis*

        Although the proper use of print screen and thumb drives could likely get past that little problem. Not that I am advocating that, but it’s not as difficult to get around as people might think. Strolling quietly away…

    1. Wendy*

      A “personal” folder was more tactful than he deserved. I would have set up a folder called “EMAILS ABOUT YOUR SCANDALOUS AFFAIR WITH [COWORKER]” and probably another one called “TACTLESS REPLIES – DO NOT FORWARD.”

      Then again, I wouldn’t last long in that job.

      2. Chinook*

        While I understand your reaction, having been the cheated on spouse, I have also been the admin. assistant a managing someone else’s inbox and, to me, that type of thing is a line too far. AAM’s advice is spot on because the OP doesn’t know further details and is just managing the mail.

        I looked at that position as the same as a mail carrier – you don’t get to judge the contents, just deliver the mail. Now, if OP’s boss had asked her to start implementing some of those personal details (like renting properties, etc.), then she would have room to push back. But rearranging documents, that is a professional nope to passing judgement.

  4. Goose*

    This whole note is ew but possibility #4 is just YUCK. Sorry you had to go through that OP and I’m really hoping it was possibility #1 or #2!

    1. juliebulie*

      Sadly, #4 was the first thing I thought of. That it amused them to make OP an unwilling witness. Especially after OP created a “personal messages” folder!

      1. AskJeeves*

        Same. The thrill of sneaking around but also parading their “secret” in front of a lowly admin who they assumed wouldn’t dare to tell…I can definitely see that being a motivation. Some people love drama!

      2. Dust Bunny*

        Same. They’ve both been made aware that the OP has to read the emails to file them and they haven’t changed the titles or, you now, set up a separate account. Its’ not like it’s hard to set up a free gmail account, for crying out loud. Five bucks says this is exhibitionism.

        1. Meg*

          That’s what came to mind as well. If exhibitionism, couldn’t that also be considered harassment? Like, an employee should not have to be reading through sexually inappropriate emails between her boss and another employee. I would b extremely uncomfortable as an employee doing that, and at the very least this should qualify as a hostile work environment?

      3. A tester, not a developer*

        Many many years ago, my company made us have a ‘buddy’ for our email – our clients wanted a personal contact, but also wanted an immediate reply no matter what, so you had to check your buddies email if they were unavailable. I was buddies with a young woman who was busy planning her engagement. She never used her work email for anything about that though – she used her work email for long discussions with the guy she had as a side piece (lots of ‘if loving you is wrong, I don’t want to be right/ ours is a forbidden love’ type stuff’). I did mention to her that as part of the buddy system, I saw the subject line and a preview of EVERY email that comes in; she was all “isn’t it so romantic? It’s like a movie!”. Luckily I moved to a new team shortly thereafter – though I do wonder what happened…

        1. Caliente*

          I wonder how romantic she would think it was if her fiancé did that to her…
          I had a friend who “fell in love” with someone else while planning her wedding and I said well why don’t you break up with fiancé…. This apparently was a very crazy idea lol. People are weird.

          1. Ryn*

            I call it “main character syndrome.” Living in the fantasy that your life is a movie any will work out with a magically happy ending because it’s what I deserve!

          2. JSPA*

            Eh, I can see it making perfect sense, depending on one’s frame of reference.

            Some people see family building as one process, and romance as another.

            It’s clearly more common in some cultures than others…but really, it’s not unknown in any, so far as I’m aware–especially taking a historical long view.

            Sure, it’s convenient in many ways when “person I want to spend my companionate time with,” “person I want to spend my sexytimes with,” “person I want to mingle genes with” and “person I want to raise offspring with” all line up perfectly.

            However, it’s not merely some modern aberration that for quite a few people, some of those things don’t align. Furthermore, the stress of forcing those things to line up (when they don’t) can blow up an otherwise mutually happy relationship; and then, you’ve blown up all of the parts that do align, at once, over whatever the one thing is, that doesn’t.

            1. PersephoneUnderground*

              It’s probably more common historically, because marriages weren’t linked to romance or even personal choice in plenty of cultures (I suppose it’s still that way in some cultures, but not as many and extremely rare in Western cultures). My husband is a romantic and gets upset when cheating comes up in movies, but at least in historical settings it helps when I point out that they probably didn’t pick their spouse, or had extremely limited options. Especially the woman.

              I do think it’s worse in modern times when you’re actively choosing to be a hypocrite though. If you’re marrying someone and you already plan to cheat, talk to them about open relationships or don’t marry them!

          3. allathian*

            Perhaps rather than breaking up, they should have discussed opening the relationship to other partners?

            One of my coworkers is in an open relationship and she just got married to her primary partner whom she lives with. I haven’t talked with her about it recently, but I assume their relationship is still open. I do know that at some point last fall, when we had one of our virtual happy hours, she mentioned that she was going on a first date that night, so it wasn’t with her fiance (at the time covid numbers were very low in my area and restaurants were open for indoor dining).

        2. nonegiven*

          I think I would have gone to HR in both cases. It amounts to sexual harassment to have to read that crap.

          1. JSPA*

            Would you also feel this way if the messages about bedsprings came from the wife, rather than the paramour? It’s hard to argue on the basis of the examples given (choosing curtains! Rental agreements! Dinner menus!) that the messages were explicit or graphic.

            OP didn’t say there was anything salacious, graphic or X-rated. Just that the messages pertained to setting up a household and relationship outside of their other, wedded relationships.

            Being aware of someone else “having a physical relationship of some sort, in the abstract” is not intrinsically harassment, regardless of whether or not it’s a relationship you approve of.

            1. allathian*

              Yeah, this. At least the VP didn’t ask the PA to run interference for him with his wife when he was on a tryst with his lover. There’s at least one letter somewhere in the AAM archives about a situation like that. This, I would hope would qualify as harassment. At the very least, it’s involving someone else in your sex life, rather like expecting your coworkers to address your bf as “master”.

      4. meyer lemon*

        It could be a combination of 1/2 and 4–kind of a power play for them to feel like they’re so high up in the company, they can be as reckless as they want.

        1. James*

          My guess is 2. They’re so high up in the company they simply no longer realize that the rules apply to them. They’ve been bending them for so long that they’ve forgotten where the line is. Saw that happen to a few higher-up executives, in finances not relationships, but it’s the same thing: bend the rules enough, and you no longer realize it’s an issue when you break them.

      5. Ama*

        Yeah, unfortunately I know someone who #4 happened to. This was in academia and her boss headed an important multi institution initiative (his office was on our floor so his staff sat near me and my coworker but we weren’t part of the same division). He only ever hired young and traditionally pretty women and made them monitor his personal AOL IM account (back when that was a thing). He knew he was getting (and sending) explicit messages to the women he was seeing on that account and he absolutely took pleasure from making his assistants read them.

        Right before I left that job, his then assistant finally got up the will to complain to our HR (we’d been trying to encourage her to, I was young and inexperienced enough then that I didn’t realize I could have gone to HR on her behalf) — they immediately found her another job elsewhere on campus and all of a sudden he had a male assistant while he was under investigation. I hope he eventually got fired but the rumor that was floating around was that he had done this at other places and that’s the real reason why the initiative’s office changed institutions every few years, so I suspect they might have just shipped him off somewhere else.

    2. TheAG*

      Same. Mostly the fact that they were using work related titles with content that didn’t match made it seem very intentional.

  5. Sue*

    I might have opened a folder, Personal-Jane or something of the sort to highlight the situation but otherwise don’t think I’d do anything differently from you did OP.

  6. sofar*

    My sister’s boss used to carry out nasty fights with her husband via her work email (which my sister was responsible for going through). She used to read them to me. Excellent entertainment.

    1. Mid*

      Yikes that’s a breach of confidence though. I get the entertainment factor, but even paraphrasing the emails is not great, and reading them to you is really, really not great.

      2. sofar*

        There’s truth to that. However, if the boss and her husband were having screaming matches in the office every single day, the employees would probably bring that juicy gossip home to their spouses/family/friends. Roughly the same as having email fights in an inbox that you know several admins are actively sorting and checking every day.

      3. JSPA*

        Yep, a clear firing offense, anywhere I’ve worked. Same as sharing details for anything else at work, that’s sensitive and not public to people on the outside, actually.

  7. Lady Heather*

    I think the small but significant difference between #1 and #2 is that #1 is they didn’t care it could make you uncomfortable and #2 is that they didn’t realize it could make you uncomfortable.

    I wonder if the emails were only as logistics-related as you described above, or if there was also innuendo and explicit comments, in which case HR might have been interested from a sexual harassment standpoint: exposing your coworkers and subordinates to details of your sex life isn’t really allowed, I think. But don’t quote me on that.

    It sounds like a horrible situation – horrible in that way only elephant-in-the-room, unacknowledged awkwardness and inappropriateness can be. I hope you’ve moved on to something better/he’s moved on to something worse.

    1. MarMar*

      Just took my yearly harassment training in the US and you’re absolutely right. The key to this one for me is “Harassment becomes unlawful where 1) enduring the offensive conduct becomes a condition of continued employment …”

      If the letter writer had to sort messages with sexual innuendo as a core job duty, that makes it harassment, even if the language was directed at someone else. If the letter writer had chosen to report this to HR, they would have had a strong argument.

      1. OhNo*

        True, but I think most harassment rules require a pattern, unless it is especially egregious. For an innuendo like that, I’d imagine it would have to happen far more than once for HR to be willing to interfere in a meaningful way (as opposed to, say, a quick “keep it PG” talk with the VP).

  8. MsMaryMary*

    This reminds me of a lighter Admin with Access to Email story. At OldJob, we had one admin per business unit and they had access to leadership’s email accounts. Generally the admins were less involved than OP; they mostly used it in case the director was unavailable or to send emails or calendar invites on their behalf. Some of the more experienced/traditional directors had the admins more involved, but many of the more hands on or tech savvy leads used auto sort and other tools to manage their email themselves.

    Our admin was known for being a bit of a busybody, and one of the younger directors figured out the admin was using her access to read her email, especially the personal messages, more or less for fun. The admin made a couple of comments about things she couldn’t have known about unless she was reading personal messages. The director was not having a secret affair and her friends thought this was hilarious. They started addressing the admin in their emails. Like, at the end of a ranty email “sorry, Pam, I’m not usually such a b*tch” or while making brunch plans “Pam, if you like french toast you have to try this place!” The admin never said anything but her knowledge of the director’s personal life seemed to trail off.

    5. OP*

      I love this – but I’d add that the only thing busybody admin likely learned was not to talk about their stalking … rather than stop stalking …

      1. Sorrischian*

        Probably, but there’s also a decent chance that the thrill for her was in the ‘I know but you don’t know I know’ aspect, so once it was clear that the secret was out, it wasn’t fun anymore.

    6. Gumby*

      I have had a few text conversations with my sister that were perfectly innocent but out of context might have looked sketchy and we’d throw in a text addressing the NSA every so often. “Hi NSA. By ‘guns’ here we mean ‘biceps.'” (Not an actual example.)

  9. Checkert*

    I’m petty, but I would’ve called the folder something far more pointed. At the least “Not Work Related”, or something like “Tryst Planning” or “Uncomfortably Personal” to start edging it closer to what I’d love to call it: “I’m not paid enough to be your pimp”

      1. Checkert*

        Not necessarily, just pointing out that pimps likely make far more than executive assistants. :D If he’d like to pay her as much as a pimp makes, then perhaps she could consider that new career focus? hahaha

    2. Dust Bunny*

      A friend of mine was cleaning up her son’s room while he was at college–looking for her missing plates and silverware–and found some written porn printed off the Internet. She had seen some odd charges on her card a couple of months earlier but they were small (a few dollars) and didn’t happen again so she forgot.

      He had a desk with a build-in file cabinet. She created a file folder for “Internet porn” and quietly filed it alphabetically with the rest of his papers, where he would know she had seen it, but never mentioned it directly.

    5. Mercurial*

      I’d go with “Grubby little affair” (or Tawdry? depends where it should be in the file list) but then I wouldn’t last long in that job…!

      1. Mallory Janis Ian*

        A file labeled “Affairs”. Then, a file within that one with “Lastname, Jane XX-XX-XXXX to Present”, leaving room for subsequent affairs. Lol

  10. juliebulie*

    I think where I would draw the line is whether or not it made extra work for me, such that I would become an accomplice. As long as I could do my job and these icky emails were not taking me out of my way, I could overlook it.

    Moving the emails into a folder is no more work than I’d do when organizing the other emails, so that’s tolerable. But if I had to lie to anyone, move the emails into secret folders (not “personal”), relay messages personally, or extend myself in any way to keep their secrets for them, at that point I would feel complicit and would have to go to HR and possibly suffer the consequences.

    Under no circumstances would I inform the spouses. Because I didn’t want to be involved in the first place, and because odds are they will find out soon enough if they don’t know already.

    1. Ali G*

      I think this is where I would be too. Maybe I watch too much soaps or read too many trashy novels, but this isn’t really that scandalous to me. It’s annoying and not very original, so I’d file it away and inwardly roll my eyes.

      1. Esmeralda*

        It’s unethical behavior, because it puts the spouses at risk physically (STDs ) and possibly financially (for instance, one or both affair partners could be fired for this behavior, if it breaks up badly one or the other affair partner could be subject to a lawsuit, etc).

        Probably violates employer’s rules.

        Potential to harm any children in one or both families.

        Not to mention breaking a serious promise — that right there would make me think twice about the integrity and trustworthiness of the affair partners.

        2. Mal*

          Nothing here except the possibility of violating company policy has anything to do with OP. Nor should it. For the sake of her own professional appearance.

        3. JSPA*

          It’s not unethical in the professional sense (except for any chain-of-command violations).

          Nobody is a mandated reporter for their coworkers’ love lives.

          We use “cheating” and “dishonesty” and “ethics” as a catch-all for very different topics. But that’s due to sloppy language and euphemism. Having sex with a non-spouse isn’t correlated to “fakes data” or “steals from the petty cash.”

          I’m guessing you would not randomly conflate “in a relationship with someone not socially-approved-by-contract” with “kicks puppies.” So why conflate it with a bunch of unrelated workplace crimes?

          1. TheAG*

            “Having sex with a non-spouse”=unwed sex. Yeah right who cares?
            In this case though I would equate it more to “Made a vow to (probably) God and everyone witnessing not to have sex with a non-spouse”. (both of the people in question are married to other people).

            So yes I would say that someone who breaks the vow is someone who also might break another social construct due to feeling they’re not bound to it or above it.

            And there was *also* a chain of command violation . He was her boss.

        4. Miss Libby*

          The boss is the one having an affair and creating all of the risks you mentioned and it is not the admin’s responsibility to mitigate said risks. I am an executive assistant and I would feel no obligation to report or address this until it started affecting my ability to do my job. In fact, I would not have even taken the step of creating a folder and filing them. I would read them, realized instantly that it was personal and ignore them.

          The admin has no moral or ethical responsibility for someone else’s actions.

    2. Shhhh*

      This is probably where I’d draw the line, too. It would still feel icky and wouldn’t be something I’d want to have to deal with, but as long as my only interaction with the situation was organizing emails within the normal bounds of my job, I don’t think I’d do anything.

  11. Dee*

    Re #4 – I wonder if they might have wanted op to know because they figured op would be descreet, and they enjoyed being able to “get away with” something.

    (If that was what was meant in Alison’s reply forgive me for repeating, I was thinking of a different connotation with that “ick”!)

    1. Ask a Manager* Post author

      I meant more the other connotation — a sexual thrill from a bystander witnessing it all / having to witness it all. Sort of involving her in their sex life without her consent. (Sorry, ugh.)

      2. chewingle*

        I wondered if it could be similar to this, but less about gratification and more about easing guilt? Like a way of confessing to the affair without enduring the consequences.

    2. ahhh*

      I was thinking this too. I was under the impression that they view OP as the “lowly admin” and could rely on OP’s discretion. It’s a horrible gray area to be in OP but I think you are doing things correctly by moving them to personal folder.

    3. Joy*

      I was wondering if OP would be able file a sexual harassment claim with HR? Since she VP is using the work email that OP has to read as part of her job, I would think this qualifies, especially since it happened many times, even after OP brought it up.

    1. Ask a Manager* Post author

      IT isn’t usually reading everyone’s emails without some specific purpose (and even if they came across these might have figured it wasn’t something they needed to report, like porn would be).

      1. Works in IT*

        If it happened to turn up in a search, we would absolutely, 100% report it, since it falls under the blanket rule of “do not use your work email for non work related things”.

        The question, though, is would it turn up, since we only run searches when investigating threats.

        1. metadata minion*

          Not all workplaces even have a “do not use work email for non-work purposes” rule, though. If I were running a side business via my work email I’m pretty sure that wouldn’t be ok, but just normal social email is fine.

      2. voyager1*

        You would be surprised though. I worked at a bank about 10 years ago that had catch phrases that were in email that would flag. Also due to FDIC regs, emails were part of the annual audit. A couple of times personal emails got caught up in that audit.

    2. Person from the Resume*

      Oh, IT is too busy doing real work to look through emails for fun. They can certainly look through someone’s email for something, but it’s only authorized on direction from higher ups (fireable offense without direction) and usually after there are suspicions for other reasons.

      1. Christmas Carol*

        I think I’d send IT an e-mail, possibly cc’ing HR and/or Legal, innocently asking how best to file these e-mails so that they would not be discoverable if either spouse files for divorce and ‘sics their lawyer on the company records. Then I would pop the popcorn.

        1. JSPA*

          So you’d have popcorn to eat after being fired?

          This was in years past, when most companies didn’t have “work email is for work only” policies even for the low level employees, let alone upper management.

          The idea that a spouse would need to dig into work emails, when there’s an actual joint second living space / bed / curtains / rental agreement makes no sense. Especially when all states have at least “soft” no fault divorce laws, and 17 only have No Fault divorce as an option.

          link to follow: those places are,
          California, Colorado, District of Columbia, Florida, Hawaii, Indiana, Iowa, Kansas,
          Kentucky, Michigan, Minnesota, Missouri, Montana, Nebraska, Nevada, Oregon,
          Washington, Wisconsin

          2. Kate*

            Even if it’s a no fault state, but a spouse is using joint assets to furnish a love nest, that’s absolutely something that comes up. Especially when said spouse tries to ding the other spouse for paying for it because they claim in court those charges for the love nest are something else.

            Unsurprisingly, people who do these things have no qualms about lying under oath, and they’ll claim that they were furnishing a personal space for themselves for after the separation.

            (Yes, this happened to me!)

          3. TheAG*

            She’d be reporting that a VP was doing it with a direct report.

            “No fault” doesn’t mean “No payout”

      2. Works in IT*

        As someone who has the authority to do this without asking higher ups first… it’s still not anything you do for FUN or you’d very rapidly get fired.

      3. Managing to Get By*

        An ex was an IT guy and he read people’s emails quite often, even though he was very busy and worked long days. He’d say something like “I was cleaning out the server and I saw…”. I worked at the same company for a few months and he always seemed to know when I was having lunch with a friend or something so I know he read my emails fairly consistently. One of the many reasons he’s an ex.

    3. Ann Perkins*

      I do email review as part of my job for regulatory reasons – emails like what the OP described would not even flag for my review. Companies that are required to have email monitoring and retention are monitoring for theft, customer complaints, insider trading, things like that – not craigslist listings and innuendos between non-spouses.

    4. FreakInTheExcelSheets*

      I’m assuming that may be part of the reason for innocuous subject lines, aside from hopefully not being stupid enough to title it “least squeaky bed for secret lovenest”. In my experience, IT has access to emails but only starts digging with cause (similar to looking at your activity – they aren’t actively watching every day but visiting certain sites may ping someone and they’ll look at your history if there’s reason) so something appearing work related wouldn’t raise any suspicions unless, like OP, they had a reason to open/read the email.

    5. NotAnotherManager!*

      I’d be more concerned about the contract reviewers who get the email for production in a litigation matter. Trust me, they’ve seen it all The Enron emails – a public data set that is used for testing and data analytics work – has affairs, offensive forwarded jokes, family photos, the whole gamut of corporate email.

      And I’ve yet to see an email review that didn’t include at least some porn.

      1. LifeBeforeCorona*

        Didn’t something similar happen during a political investigation in Washington years ago? An affair between two married people was discovered while investigators were looking for something else? My memory is hazy but it goes back to never put in writing anything you don’t want read out loud in court.

    6. ForReal*

      I know an IT guy who said he would never who look at the email/activity of people who are above him in seniority/in some way his boss. I don’t blame him, and I’d bet it’s common.

  13. Jamie Starr*

    Could they possibly have been completely oblivious that OP literally had access to read the emails? At old job, our Exec. Assist. had access to the Director’s inbox. This was (I thought) common knowledge — the staff knew it and understood that anything emailed to Director could conceivably be read by Exec. Assist. The only person who couldn’t seemingly grasp this concept was the Director himself. I tried to explain it to him (it came up because I was HR and also the IT liaison) – yes, having access to your inbox means she can see/read all of it. (I don’t know how he thought she would draft emails or manage his calendar appointments without being able to read his emails.) This was a person who was averagely tech-savvy; maybe it was denial.

    1. Myrin*

      That’s fascinating – what did Director think “access to inbox” meant if not being able to at the very least see/read the messages?

      But also, OP says she told both people that she “often needed to open and read them to see if they needed [her] action” which seems pretty straightforward.

      1. Jamie Starr*

        I really have no idea. The other odd thing about it was that this was his second EA. I asked him when she was hired if he wanted her to have access to his email like [Previous EA] and he said yes. He caught EA #2 reading her own evaluation (that he had emailed to his supervisor) before they had the meeting to discuss it and that is how/why I was drawn into it.

    2. Smithy*

      I do think that options #1 & #2 often come into play in creating a level of obliviousness. Not so much where they do or don’t know that emails are being read, but that part of why they’re being read is for that person stops thinking about every detail.

      Like, if you hire someone or a service to do your laundry, that can involve someone seeing/touching/handing undergarments. While in broad strokes, the intentional goal was to get help with laundry – it’s rarely with a desire to deeply consider what a housekeeper or laundromat staff are going to think about your clothing. Including the more intimate pieces.

      I think that people bring a lot of different intentions to those relationships, but I think a huge component of this is “think about it so I don’t have to.” In the LW’s case, the unprofessional nature of the work request is incredibly unfortunate, but unfortunately agree that there’s likely very little the OP could have done without professional repercussions.

  14. No one told me life would be this hard*

    Just as a for-instance, if the two were ever cited in a divorce proceedings under adultery, I assume the OP would have to divulge if subpoenaed?

    2. Family Lawyer in a Past Life*

      In theory, yes. In practice, the lawyer for the other side has to know exactly who to subpoena. They would have had to ask discovery questions of the other party in exactly the right way to find out the OP’s identity and whether they had access to the emails and then subpoena them. In many states, (mine is very permissible about relevance when it comes to the rules of evidence) you can subpoena anyone who has knowledge of an issue at controversy. Subpoenaing the OP seems like a lot of work for the VP’s wife’s lawyer. They could easily just subpoena the VP or Affair Partner and make them testify about the emails. If they know about the emails already they would have to be produced through discovery.

    3. JB*

      I would think they would be far more likely to try and subpoena the company to get actual copies of the emails, rather than LW for her recollection/experience of having read them.

  15. Nonclumping Formula*

    This happened to me as a young assistant. I had no patience for it, and was so offended that my boss thought it was okay for her to tell me to ‘check into’ her email and just ignore gross messages from the man she was cheating on her husband with. So I went into her office and told her she should set up a personal email account. It took her a second to realize what I was saying, then she turned bright red, agreed, and that was that. And after that she became super skilled at minimizing her screen anytime someone came into her office.

    1. bleh*

      Gonna guess not every boss would be shamed. Many would just fire you for having the temerity to say something.

  16. Noncompliance Officer*

    I work in the public sector. Years ago when I took a workshop from our state archives, they went over public requests for information and showed an example of how someone’s affair got swept up in a request and published in a lawsuit because they were using their personal email to conduct the affair.

    1. All Het Up About It*

      I just started a government job, and ended up with access to some past employees emails for varying complicated reasons. I was appalled to see some of the personal things in them. Nothing icky like this, but someone was apparently suing for custody of a child and was using their work email to communicate about the case, including financial and legal documents. I honestly haven’t dug into the details of it, because it has no baring on my work or why I have access, but I totally think about something like this happening with them.

      Your work email is not YOUR email, and it certainly isn’t if you work for a government entity where public record requests are a thing.

      1. FreakInTheExcelSheets*

        “Your work email is not YOUR email” – this seems to be something a lot of people don’t get. Especially people like my dad, who worked for the same company for 25+ years and his work email was LITERALLY the only email address he had. To my knowledge, he didn’t use it for anything questionable, but I did have to help him extract his contacts and set up a personal account when he was getting ready to retire. And now we keep finding other accounts where he used it and now can’t access the email account to reset a password/change the email (like REI – he’s ticked about possibly losing access to their rewards lol).

        1. E*

          Exactly the situation with my dad! He’s finally set up a gmail account now that he’s retired… except that he moved seamlessly into consulting 3 days a week with the same company and mostly doesn’t use the gmail account.

    2. OyHiOh*

      I just had a conversation with my boss about tone in email! He came in to vent frustration before writing a more appropriate response. Our org is subject to public records requests and the language he felt like using would not be complimentary to the org if printed on the front page of the newspaper.

      That’s our organization’s standard: Don’t write anything you wouldn’t be ok seeing on the front page of the paper. Not in notes, not in documents, definitely not in emails.

    3. Insert Clever Name Here*

      There is a very interesting episode of the podcast 99% Invisible about the emails of Enron employees that were released during that investigation in the early aughts, and there are definitely emails in that population about divorces, hook ups, and drugs in addition to the instances of accounting fraud.

      2. NotAnotherManager!*

        This data is well-traveled, too – nearly all legal review database providers use this corpus as their demo data set. Everyone in the ediscovery industry has seen these emails ad nauseum, and they’re also big in the data analytics sector, too, because it’s one of the largest publicly-available email sets for testing. (It was the Microsoft antitrust emails before the Enron set was published.)

    4. Sasanach in the states*

      I want to clarify, because this seems to have been overlooked and is IMPORTANT, but you state that the employee’s PERSONAL email account was subpoenaed, most likely because at some point, they used it for business purposes and became discoverable, correct? If so, employees BEWARE! (even if you aren’t having an affair)

  17. GreenDoor*

    In my job I often become privvy to a LOT of personal information about people. When to be discrete and when to tell? My baromoter is always “to what extent does this information affect the work of my organization getting done?” So, details about potential criminal activity related to the org, direct violation of personnel rules, misconduct involving children we serve…..I’d report it. Nasty back and forth between an employee and his soon to be ex spouse, a joke about a two hour lunch going unnoticed, Jane calling Betsy names? That’s just idle gossip that can die with me.

    So, unless OP’s workplace had a specific ban on VP’s having personal relationships with subordinates, or unless the VP is showing obvious favoritism or other employees are facing harm or some obstruction getting their actual work done, I’d’ve let this go. Maybe had a conversation asking for a clearer subject line. But that’s about it.

  18. OP*

    Hi all – OP here. Yeah, the whole thing was just EWWWW.
    I would not do the forward-to-spouses thing. That sounds horrible for everybody involved, including me.
    Definitely wasn’t #3 due to our industry. I’m hoping it was #2, but likely a little dash of #1 in there … I can see the subordinate being a #4 (ugh) and am relieved that I don’t know for certain.
    Thanks Alison for your advice, and commenters for input! (And Alison: thanks for the praise re: my ghostwriting – I was quietly proud of that too, but of course couldn’t brag about it to anybody!)

    * One little bias-check nudge for all of us, though: my letter only identified the gender of VP, and people have assumed both that the relationships are hetero and that I am a female executive assistant. I never mentioned those details in my email. Gentle reminder that not everything is always as MadMen as the VP :)

    2. Elenna*

      …I just now realized that I’ve been assuming that both the affair partners were male and they were married to women. Don’t ask me why I assumed that, probably a different sort of bias? :P

      But yes, thanks for the bias-check reminder!

    3. Jen*

      Kudos OP on not gossiping about it once they were gone. I’m not sure I could have kept my mouth shut once I knew they were both fired! That’s top notch office tea!

    4. Alldogsarepuppies*

      Its more Alison training us to use female pronouns/assumptions when not being told otherwise – long been the default of this blog.

    5. priority cat*

      Huh? But OP, you are the one who said “Madmen VP” so the commenters jumping to the conclusion that he was like Don Draper (male, womanizer) doesn’t seem like bias?

    6. RagingADHD*

      I think if you aren’t intending to portray a male boss taking advantage of female subordinates (plural), using Mad Men was either a fundamental misunderstanding of the show, or a deliberate attempt to play “gotcha.”

      It’s not a show about work affairs. Its core themes are about misogyny. Using it doesn’t obscure the genders in the story, it creates a very specific set of assumptions that are implicit to the metaphor you chose.

  20. Anon Today*

    Part of my job entails going through emails of people who have left to comb out things the team might need: contact information, status reports, the back-and-forth on a negotiation that isn’t settled. It’s usually very boring and is mostly a keyword search plus filing job. Except for the guy and his affair partner, both employees, who would check in on the Smith account or the Roberts contract and then get into explicit rehashing of last night’s fun. EEE-yuck. And no surprise that each was let go for ethical lapses (not the affiar, regarding money/contracts/conflicts of interest).

  21. Jennifer*

    Of all the suggestions, I think #1 is most likely. They viewed you as “the help” and didn’t care if you knew. Ask anyone who has worked a service job or worked in someone’s private home. People say all kinds of outrageous things around you and they really don’t care if you hear them because in their minds you don’t matter. Glad these two are gone.

    1. Elenna*

      I’m reminded of a Harry Potter fanfic where some of the protagonists started a fancy restaurant in Diagon Alley, so that they could easily listen in on rich bigoted purebloods who were used to “the help” being house-elves and didn’t even think about the (human) waiters :D

      1. FreakInTheExcelSheets*

        I’m pretty sure I’ve read this one :) Or a similar one where they did use house elves as service staff for the same reason.

  22. China Girl On the Shelf*

    Re: “resignations were often discussed as “no loss,”

    I couldn’t help but think of the lyrics to Julie Brown’s song “Homecoming Queen’s Got a Gun”:

    “An hour later the cops arrived
    By then the entire glee club had died, no big loss..”

    I am clearly going to hell.

    1. James*

      I mean, if someone read some of my IMs with a few coworkers they’d come across some stuff that doesn’t look professional. We work really well together, but our way of talking to each other is….let’s just say we started out working behind drill rigs and it shows. I’m willing to give people the benefit of the doubt when it comes to stuff like that. “Your name is in the mouths of others–make sure it has teeth” cuts both ways, and office workers gossip. It’s part of the job.

      I’m not saying that people should be badmouthing others behind their backs consistently, or that we should excuse bullying. I’m just saying that there’s a difference between bullying and venting.

  23. MLH*

    I’d be like “while sorting through your personal messages I saw your email noting that you were going to give me 3 extra weeks of vacation for my excellent work! Thanks so much!” lol

  24. Tangerina Warbleworth*

    OP, please please please write a book and use these! If you hear from one of these clowns you can always just blink your eyes innocently and say, “But this is fiction….”

    Yeah, I know, liability, since the emails actually belong to the company, but it’s still fun to think about.

  25. I'm thankful I'm too lazy to have a workplace affair*

    I would love to find a way to include your emails as a bullet point in a resume! That would be a fun way to be creative, if only it was for fun.
    * responsible for the mental health of 7 colleagues during lay-offs

    A decade ago I was at a workplace where we found out that a Very Senior Person was having an affair with a subordinate. It was very clearly against the rules (a fireable offense due to specific circumstances), but what totally Blew. My. Mind. was that the VSP decided to run the affair from his work account! He would have had some plausible deniability and maybe had a chance of keeping his job if he had created an email account from scratch as there would have been no proof. I think he would have still been in big trouble, and likely fired anyway, but based on the stuff that came out in public it appears that he also nailed his coffin completely shut when he asked the IT department to delete his emails. One was bad judgement in his personal life, the other was bad judgement in his professional life (and had legal repurcussions, which ended up in the news). Why are people having affairs so stupid?!?!! (I know, I know, the blood was at the wrong end of the spine, but the thoughtlessness surprises me)

    2. Working Rachel*

      Of course, the R. Kelly situation is different from the sort of situation described here–R. Kelly was/is a serial predator, and the two people described here were engaged in a consensual relationship, albeit one that was presumably not condoned by their spouses or the company they worked for. I would argue that in the former case one DOES have a moral obligation to inform on one’s boss (to the authorities), while in the latter keeping one’s mouth shut is much more morally defensible.

      1. I'm thankful I'm too lazy to have a workplace affair*

        Oh if there is anything predatory then definitely a different situation! In the situation I experienced-at-a-distance, it was completely consensual although there was some ‘I really love you and will leave my partner for you’ lying, and the other person was devastated to discover that they were one of many affairs (although another complaint – why are some people who participate in an affair shocked to discover the other person isn’t loyal?!!).

        People should learn to keep affairs personal, and keep it out of work emails. It would have been so much easier for the OP!

        1. tangerineRose*

          “why are some people who participate in an affair shocked to discover the other person isn’t loyal?!!” Yeah, this!

      2. I'm thankful I'm too lazy to have a workplace affair*

        Just noticed this was a more relevant response to the comment below – sorry for the tangent rant!

  26. Anonymous for This One*

    Several years ago, I had a situation where a very close friend and her husband saw my then husband out at a restaurant with another woman, This turned out to be the woman he left me for (don’t feel badly, it was a blessing). My friend and her husband decided NOT to tell me at the time, and I still feel some type of way about it. Her husband had been a serial cheater, so of course he identified with my ex. But I feel my friend’s loyalty should have been to me. Why should everyone know about the infidelity except the one being cheated on? Why should the cheating spouse be enabled by a friend of the non-cheating spouse? I felt foolish once the friend did reveal that she had this information, and yes, I questioned the friendship. I could not have behave normally with my friend if the situation had been reversed.

    A work situation is different. It feels a little dirty to be involved with these communications, and I would ask not to be a party to them. But informing the spouse in this situation would be a bridge too far as there is no relationship between the OP and the spouse. It’s unfortunate, but personal assistants are often called to cover up the misbehavior of their employers, especially when it comes to celebrities. No question to me that the covering up isn’t much better than the behavior of the perpetrator (think child molester R. Kelly and his merry band of enablers, ugh). At some point, a person in this position has to decide what their moral limit is.

    1. Lisa*

      I likely wouldn’t say anything because I know men and women can be friends, and I would not have jumped to conclusions. Unless, of course, you mean they witnessed what was obviously a date instead of just 2 people having a meal.

      Question though – would you have believed your friend if she told you? Or would you have been mad at her or maybe told her she was lying? Be honest. Because what you are saying now is that you are mad at *her* because *you* felt foolish, but you’re covering that up with a story about disloyalty. Sounds like she was going to lose no matter what.

      1. Sandi*

        Agreed that your question is valid, Lisa, I was thinking the same. I have been in this situation, although with a coworker rather than a friend, and I told them although it was by accident (the coworker had broken up with her boyfriend, but had recently resumed the relationship). I was never believed, which is completely fair, but I learned the deeper meaning of the expression ‘shoot the messenger’.

        Suspicion isn’t the same as fact. My neighbor told me about how a ‘friend’ confidently told her husband about the affair that she was having behind his back. Thankfully the husband was able to laugh quite hard at the time, and later said to his wife/my neighbor “You won’t believe what your friend thinks you’re doing with your brother (who is visiting from out of town)!”

        1. Anonymous for This One*

          My situation wasn’t a believe it or not thing, both my friend and her husband witnessed my ex dining with another woman in a romantic manner. It was a fact. They did not need to draw any conclusions or report that my husband was having an affair, just say what they saw. Gossip isn’t facts.

          It’s ironic, because this friend’s husband is a serial cheater who has given her a venereal disease while they have been married. Maybe if somebody had told her something, she wouldn’t have gotten sick. She stays with him despite this and many other things. She probably would not want to know if I saw him romancing some woman, because her ability to delude herself is what has kept her married to him for a long time.

          It’s a moral stand that each person has to decide for themselves, based on the relationships involved and the facts and circumstances of the particular situation. I ended up divorcing my ex over his infidelity, but may have done it sooner if my friend has spoken up at the time and not after I had already divorced him.

          To each their own.

          1. The Gollux, Not a Mere Device*

            I don’t know what I would have done in that situation, but it sounds like your friend didn’t tell you what she saw because she wouldn’t have wanted you to tell her if it was the other way around. Most people’s yardstick for questions where there isn’t a cultural-consensus answer is imagining themselves in the situation. So the husband was probably thinking “I wouldn’t want someone to tell my wife I was cheating,” and your friend was probably thinking “I would rather not know, if someone saw Husband having a romantic dinner with another woman.”

            Like you, I don’t see why she told you after you divorced the guy, when the information couldn’t be of any use to you.

          2. tangerineRose*

            I wish your friend had told you. I agree; she was your friend, so she should have told you.

            I think the LW was smart to not tell the spouse, since she didn’t know the spouse and talking about this might have blown up the LW’s life.

      2. Anonymous for This One*

        However, just mentioning you saw somebody’s spouse out with another person doesn’t mean they aren’t friends. If it’s my husbands friend, I should know the person or be able to ask him about the outing. It isn’t jumping to conclusions to mention you saw the spouse of a friend at a restaurant, no matter who they were with. The not mentioning it makes it seem nefarious. And yes, my friend and her husband felt they saw a date going on. They didn’t tell me they saw him till long after we were divorced, I didn’t understand that either. No point to telling me this then.

        I knew my ex was a philanderer, and yes, I would have definitely believed her. It’s rarely a surprise when a spouse is cheating. I don’t quite follow your point about the friend losing no matter what. She had no reason at all to lie, and I felt foolish because she knew something about my personal life that I didn’t. Not covering up anything, I do think she committed a disloyal act. We’re still friends. and have been for fifty years, this is no casual friendship. I’m not “mad” at her, I just feel some type of way about how she handled this, and wish she had handled it differently. She never sees my ex anymore (that I know of, lol), but still sees me.

        There are people who don’t want to know the truth, but I’m not one of them. It can be fraught with peril to share this kind of information, but I bet my friend told somebody other than me about seeing my ex with a woman, because people like to gossip. Rather than gossip, tell your friend things like this, observed with your own eyes.

    3. Working Rachel*

      Of course, the R. Kelly situation is different from the sort of situation described here–R. Kelly was/is a serial predator, and the two people described here were engaged in a consensual relationship, albeit one that was presumably not condoned by their spouses or the company they worked for. I would argue that in the former case one DOES have a moral obligation to inform on one’s boss (to the authorities), while in the latter keeping one’s mouth shut is much more morally defensible.

  27. PT*

    My mom had a job like this, back in the Mad Men days (the late 60s to early 80s) and said a huge key part of getting the “executive” support roles was managing the schedule and phone calls efficiently such that the wife never found out about the mistress, and vice versa.

    Apparently occasionally someone’s admin would get fired for saying, “Oh hello you must be [wife]!” when they ran into Boss and the mistress on the street, or “Oh did you have fun in the Bahamas last weekend?” while patching the wife through to his direct line when he’d actually traveled there with the mistress and told the wife he was at the Cleveland office putting out fires.

    But in OP’s shoes, I’d just flag the affair partner’s address as spam.

    2. I Wrote This in the Bathroom*

      That explains why our river caught on fire, bossman was supposed to put it out and took his mistress to the Bahamas instead, the dork.

  28. Bob*

    In most organizations they reserve the right to read anything that enters or exits their servers, so in that vein would whistleblowing or an anonymous tip to HR that they should review the e-mails of these two have worked out?

    1. Tired of Covid-and People*

      It always amazes me that people think there is anything private about work email. Those messages could have ended up on the evening news. It’s just stupid.

  30. Anne Elliot*

    This brings up memories of more than a decade ago when, as a new attorney, I did document review work for a while and would have to read these exact types of emails, including how they started out professional-seeming and then took a wholly unexpected turn. “From: Male CEO, To: Attractive Female SVP. Re: This morning’s meeting. Pick one of the following, a ruler, a hairbrush, a belt . . .” (Me in my head: What the hell is this?) “. . . . because you have been a very naughty girl . . .” (Me: Uh oh.) ” . . . much spanky-spanky talk,” very boring two years later, read by stranger at 10 in the morning. WHY do people do this. Work email is NOT private.

    1. Hoya Lawya*

      I had exactly the same experience. One well-known company sued another, and you found out lots of inconvenient truths about people’s private lives.

  31. Properlike*

    If this is Hollywood, then it’s part of the job description. At least it’s only one affair at one time, and you’re not making travel arrangements for the couple(s) and then having to remember where to tell his wife he *really* is this week.

  32. LGC*

    …what in the Enron Corpus

    That’s…that’s it. When I said the letters the past couple of days have been wild, I wasn’t expecting quite this wild. I salute you for your service, LW.

  33. Tuesday*

    I have a theory about social media that says that when people post something, they’re only thinking about their intended audience, not all the people who are actually going to see the post. Like, “My friends from college will find this hilarious”… but they don’t give a thought to what great aunt Melba, or their mother in-law, or their coworker, or whoever will think. Maybe it’s kind of the same thing here.

  34. Swamp_Witch*

    Nope yuck no. I had a charismatic, gruff-mad-men-type boss as an assistant and nope yuck no. I had to go through employee phones (that we supplied) do updates and handle upgrades, wiping the phones for new employees, stuff like that, and both the men I was an assistant to had junk pics on there and stuff to and from female staff. One of them was also having emotional (at least I think it was only emotional) affairs with at least three other women in the building. He used my discomfort and complaints (come on, it’s harassment to know I’m going to be wiping your eggplant pics off your old phone. Nobody forgets about that stuff, it was a deliberate power move) to spin it to corporate and our executive team that I was untrustworthy. SO NOPE. Any boss that does that is being abusive to their staff.

  35. NYwriter*

    I agree that the boss just didn’t care if the assistant saw it. In my first job after college (a creative field) our boss was having an affair with one of the people whose work we were dealing with. I don’t know if they sent sexy emails, although she did have an executive assistant who had to go through her emails for her and write replies to people (our boss didn’t “do email,” she had the assistant print out all the messages & then she’d scrawl her reply on the print out & her assistant had to go in & send it—but I digress).

    We all knew about the affair, however, because her lover lived in a small city & boss always had an inexplicable layover there—like, every time she flew from NYC to LA she had an overnight stopover in Cedar Rapids (not the real city, but it was equally random). And her hotel bills there (and sometimes in LA & other places where her husband definitely had not joined her on her business trip), there were always 2 breakfasts charged to her corporate card.

    We all knew, and she didn’t care.

  36. All Outrage, All The Time*

    I’m an EA and I see all manner of eye watering emails. I keep everything confidential and figure if my boss was concerned about me seeing it, they would have used their personal email. As long as I’m not asked to do anything to contribute to their personal situation in a way that made me uncomfortable, I just turn a blind eye. When you’re an EA , you’re bound to over hear or be exposed to personal matters. The key is to be very discrete, keep the confidence, and get on with the rest of your work. If you’re bothered by your boss having an affair, or seeing personal emails, you need to find a different job. My boss could carry on 50 affairs and as long as I wasn’t asked to participate in deception or use company time to order coasters for the love nest or what have you, I’d just ignore it.

    1. That's Ms to you*

      Nope. Not even close, because there are thousands–nay, tens of thousands or more–bosses exactly like this. It’s so common it’s not funny, it’s just sad.

      Now, if he had the OP pick up his Viagara, deliver it to the love nest with whipped cream and a bottle of champagne, he might be in the running!

  39. Raine*

    Speaking as a former exec admin – those C-suite people didn’t care, saw the EA as “the help”, and expected the EA to keep their mouth shut or else. I worked as a temp EA for five years – met many a C-suite who thought I had no better than an eighth-grade education and just hopped off the turnip truck.

    To the OP – you were between a rock and a hard place, and I’m glad to know you’re no longer there.

  40. FormerExecAssistant*

    I used to be an Executive Assistant and my boss (the CEO) would frequently exchange very frank opinions over email with various people in the company. It came back to bite the company, however, as one of the senior managers left and decided to try and sue the company for unfair dismissal. They put in a subject access request for all the emails sent with their name on it within a set period (2 years or so). It was… a lot. After that, the emails really calmed down! Sometimes I think it takes an experience like that for it to sink in that company emails aren’t necessarily always going to be private.

  41. Magie*

    I could have written this. My ex-boss had a tempestuous affair and continued exchanging salacious and emotional emails with the woman while I managed his inbox. I also didn’t do anything while I was employed by him, because he was vindictive, petty, and astonishingly insecure, but I sure as hell brought it up in my exit interview.

  42. ExecutiveAssistant Here*

    I’ve been a C-level Executive Assistant for 10 years and can tell you that discretion and confidentiality are two of the most important qualities. In fact, those exact words are in my job description! Over the course of my career I have been exposed to many secrets – some were scandalous and others were simply extremely personal. In all scenarios, I have kept my mouth shut.

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