my boss books escorts with his company email

by Alison Green on May 8, 2017

A reader writes:

I’m an executive assistant (female) and have worked with my executive (male) for nearly two years now. He’s a good guy to work for. I’m challenged in my job and I never have to worry about what he thinks about my work. He and I get along and have a good working relationship with a lot of trust. Sometimes my work will extend a little bit into his personal life (writing an email on behalf of his child’s extracurricular activities, coordinating travel with his wife, picking up his dry cleaning), but it’s minimal. He has a long-time spouse (20+ years) and a couple of kids.

Said boss always like to tout that he’s faithful and pious man, and that stronger men than himself have made dumb decisions and have been unfaithful to their spouses. He claims he’s never even had a fleeting thought of being adulterous. His marriage seems lovely and perfect.

But about six months ago, I was given access to his email. I was going through his Sent folder to find an email he was referencing, and I found a strange gmail account. The email was short, and boss was asking the recipient if she “had time to meet today.” I thought, perhaps this is a recruiting candidate that we’re looking at. So, I googled the email, and it came up as an escort (read: prostitute) for our city. I was flabbergasted. Intrigued, and wondering if somebody had hacked his account, I dug a little deeper and found a different email address. I also searched it, and it was another escort in our area. And I did confirm that it was my boss who was writing these emails because he shared his cell phone with them.

So, in these past six months, every now and again I’ll find an email to/from an escort. They are never the same, and when I search their email on the web, sure enough, they come up as an escort. Should I bring this to his attention that I know? That it is INCREDIBLY risky for him to use his work email for this? I kind of want to call him out on it so he realizes how conspicuous he’s being.

I get it — he can do what he wants. Maybe his spouse is in on it. Who am I to judge? But what irks me the most is that he does this on company time (for example, he goes and tells me that he has a “meeting” with a recruit at a nearby hotel, but I surmise he’s seeing the escort because of the emails and because he actually books a room — I have access to his hotel account). What do I do? I intend on looking for work soon, for this and other reasons.

I don’t think you need to do anything here, really.

He presumably should already know that it’s risky to use work emails to set up appointments with sex workers and yet he’s doing it anyway. It’s not your job to protect him from himself — not when doing so would mean potentially creating the kind of tension and awkwardness that could impact your quality of life at work and even your job security. Of course, maybe it wouldn’t go in that direction at all — maybe he would be grateful and lovely about it and surprisingly not awkward at all — although “not awkward” is not typically how people describe this kind of conversation. Regardless, though, there’s not really an incentive here for you to take on any risk to yourself just to point out something that should already be blindingly obvious to him.

Now, if the emails were graphic or something, and you were being subjected to them in the normal course of doing your job, it would be reasonable for you to say, “Hey, your personal life is your business, but I need to access your email for work and I don’t want to have to read this stuff.” But that’s not the case here — you’ve had to go out of your way to figure out what the emails are.

For what it’s worth, though, it’s pretty weird that he felt the need to proclaim to his assistant that “he’s never even had a fleeting thought of being adulterous.” That kind of thing always sounds to me like the person is announcing “I might want to cheat on my wife,” both because it’s so needlessly defensive (no one was accusing you, dude) and because people who feel comfortable with the commitments they’ve made don’t generally feel the need to go around talking about how great they are for keeping those commitments.

But weird as your boss is with his fake piety, ultimately it’s not your business. He doesn’t require you risking yourself to protect him, and you can just roll your eyes and know that you’ll forever have a good story to tell.

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{ 478 comments… read them below }

  1. Stephanie*

    Yeaaaahhhh, Alison’s advice is spot on. I would just stay as far away from this as possible–he doesn’t sound like he’s being especially discreet (especially given the conspicuous fake piety), so I imagine this will blow up at some point.

    1. Falling Diphthong*

      Anecdotally (via advice columns) I have concluded that everyone having an affair believes that they are doing an impenetrable job of covering up, no matter how laughable this looks to a third party, and so when someone finds out their response is rage at the messenger. Only by cheating and betrayal could the messenger have figured out their… cheating and betrayal. Probably a cause-effect link there.

      There is a tiny chance your boss would react with humble gratitude–surely someone has had this reaction at some point–but it is dwarfed by the chance that he will realize he must make your work life hell. Since observing the evidence of infidelity will be proof of your cheating and betraying your job. Drumming up an excuse to fire you seems very on the table. Leave it alone.

      1. AthenaC*

        In fairness, people who are actually doing an impenetrable job of covering up aren’t likely to be the subject of advice column questions. ;)

      2. Indie*

        This is so true. I remember an old married boss who was sleeping with his assistant. It was visible from outer space. She was really annoyed with her best friend when word got out. ‘She was the only one who knew!’ Nope. No she wasn’t.

    2. Annonymouse*

      I’ve also got to ask:
      OP in bringing this up what do you hope to gain?

      If it’s your hope he will stop and be the man he claims to be then you are going to be waiting until the next life.

      If it is that he stops using the work email that might be something he can do but he is still going to be cheating. Are you comfortable with that?

      It really sounds like you hope he knocks it off but to be honest you don’t really have the standing to ask.

      It isn’t blatant, in your face, regular part of your work (like the assistant who actually had to hide her bosses multiple affairs)

      You don’t have a close friendship with him or his wife.

      He isn’t abusing company funds for it.

      In fact you have to really search for the information about what he is doing.

      I’m not defending him, believe me, I don’t think cheating is ok.

      But the risk of you speaking up and getting fired/having your work life made hell is high when currently the cost of ignoring this is low.

      1. Zombii*

        >>It isn’t blatant, in your face, regular part of your work

        This is where I got confused. The OP referred to her boss’s cheating as “conspicuous” but all I’m seeing is the occasional meeting set up via his work email and a hotel reservation. She figured it out by googling the email addresses, because the emails were vague and… she wanted to know what the vague emails were about/who he was emailing. That part seems a little weird to me but I’ve never been an EA so maybe that’s normal.

        It sounds like OP is at the BEC point with her boss, and I’m wondering what the “other reasons” in “looking for work soon, for this and other reasons” are, because this one thing seems minor and fairly discreet.

        1. Indie*

          I have to agree. I’d personally hate to be around blatant infidelity happening in front of me but this was more like a decent bit of sluething on OPs part. I think he got her spidey senses tingling with the crimson flag of unsolicited reassurances; so much so that she couldn’t resist following up the lead. THAT is the blatant bit imo, and if he makes a habit of pontificating about his values, I can see why she’s checking the exits.

  2. EA*

    HAHAHAHAHAH

    Oh boy.

    The only thought I have, is that this is one of the most entertaining parts of being an executive assistant. I have had weird wife issues in all the jobs I have had. Currently my boss’ wife calls him constantly, and I dodge all of her calls, because that is less awkward than being like “she has called for the 4th time”, and have him lie about getting back to her. I would find humor in it, but I have a pretty caustic sense of humor, and no great respect or admiration for any of my bosses.

    1. Cambridge Comma*

      I’d be incredibly tempted to particularly ask him how his wife is, what the family are up to etc. before and after these appointments. It’s probably good that I don’t have OP’s job.

        1. Kristine*

          This is best left alone but I have to admit that I would be VERY tempted to tell him, “My high school friend [escort’s name] wants to break into our industry after many years of – er, freelance. Would you possibly be willing to give her an informational interview?” Trade Ack! for Ick. :P
          No, I’m so glad I’m not in OP’s position!

    2. Manders*

      When I did som EA-type duties for the owner of a small family business, I used to pretend I was one of the maids from Downton Abbey. Be unobtrusive, make sure the family never ever has to notice the problems I take care of, keep the family’s scandalous secrets…

      (Hoo boy, were there some scandalous secrets!)

      1. RVA Cat*

        Here’s hoping you never had to remove a corpse from your employer’s bedroom….

        1. Manders*

          He was a surgeon, so he’d definitely dealt with corpses (although, fortunately, not as part of the business I handled for him).

          He was a lot like Lord Grantham, actually: alternated between not paying attention to finances and panicking about them, had a habit of mistaking work relationships for friendships, had several indolent kids who always had some kind of drama going on.

  3. Hey Karma, Over here.*

    Tell priest, tell a therapist, tell your hairdresser. Then let it go.

      2. The Not Mad But Occasionally Irritable Scientist*

        Manicure salon techs, too. I imagine they hear EVERYTHING as they toil away buffing toenails and such.

        1. Emi.*

          One of my favorite book characters ran a manicure salon staffed entirely by Asian women who pretended not to understand English so they could collect gossip, political intelligence, and stock tips from their clients’ conversations with each other.

          1. Countess Boochie Flagrante*

            This sounds amazing, and I’d love to get the title/author!

            1. Emi.*

              It was Kiki Strike Inside the Shadow City, by Kirsten Miller, but I’m afraid the spy salon wasn’t the main point of the book. It’s about a bunch of twelve-year-old girls who explore an underground city beneath Manhattan, and this is how Oona invests her share of the treasure.

      3. Life is Good*

        Yeah, but they also often spread it, too…and mine does with names. The reason I keep my part of the conversation very superficial. She is really good with hair, though!

        1. Say Thanks A-Latte One More Time!*

          Oh please don’t! I used to be a barista and I had a married couple come in to have coffee every morning together at 6am. They would engage in a lot of PDA and talking really close to each other, no problem except… they weren’t married to each other! It was awkward and yucky. I didn’t want to know about it. I also didn’t want to know about people’s health problems and other drama.

          The worst part is that you’re stuck behind a counter with no place to escape to so they basically have you hostage.

    1. Ann Furthermore*

      Yep. Show me someone pious and self-righteous shouting from the rooftops about how virtuous and perfect they are, and I’ll show you someone secretly engaging in the very behavior they’re so loudly rallying against.

      1. N*

        Yes, it makes me think of the lw who called her boss’ daughter a @#$&! a few weeks ago based on her strong Christian upbringing.

        1. Decima Dewey*

          To quote Dorothy Parker:

          “Lady, lady, should you meet One whose ways are all discreet, One who murmurs that his wife Is the lodestar of his life, One who keeps assuring you That he never was untrue, Never loved another one… Lady, lady, better run!”

      2. Liane*

        This kind of thing always reminds me of what is supposedly a French proverb: “Only a man who has hidden behind a bedroom door would look there.”

      3. AnotherAlison*

        Sorry, Ann, you just don’t understand why it’s different for them and the rules do not apply to them. They are virtuous at heart, just victims of circumstance. /sarcasm off

        1. Allison*

          See, when these men cheat, they do it for a good reason. Not like all those other men.

          The only virtuous affair is my affair.

          1. nonegiven*

            It’s always possible that he likes to just talk.

            Not likely, but possible.

            1. Annonymouse*

              They might not be doing the deed.

              Some people visit escorts for very weird reasons – make the person pretend they’re a cat, spend the whole time letting him stroke their feet etc.

              Technically not cheating.

      4. Greg*

        “I’m the furthest thing from a racist, but …”

        Whatever follows is pretty much guaranteed to be incredibly racist.

        1. HannahS*

          I always feel like interrupting them.
          “I’m not racist, but—” “EXCELLENT, good for you! I’m glad to hear it. Nothing further needs to be said.”

          1. Chalupa Batman*

            Please do that! “Now, I’m not racist-” “That’s awesome. You’d be surprised how many people say that right before saying something super racist. Isn’t that strange?”

          2. Lissa*

            I’ve always wanted to start using that to start sentences that actually aren’t racist. “I’m not racist, but kittens are really cute!”

            1. blackcat*

              Actual sentence said to me:
              “You know, it seems almost like cat-racism, but I swear I’m extra allergic to black cats.”

              (I am not, in fact, a black cat. But I do have one).

          3. EA*

            Or just pull a line from Avenue Q – “Everyone’s a little bit racist, sometimes”

      5. Stranger than fiction*

        Yep, one of them just got fired where I work and that describes them perfectly.

    2. Here we go again*

      I had this exact thought….

      OP, I think you have to let this go. If this affects how you view your manager (it totally would for me), you are free to look for a new job, but otherwise, just ignore it and pretend it didn’t happen.

      1. Falling Diphthong*

        I think affairs go into a weird category where it is a violation he probably cares deeply about keeping secret, but the company (probably) doesn’t care because it doesn’t strongly affect work–it’s not like embezzlement or leaking trade secrets. Maybe along the lines of claiming they leave early a couple of days a month to “help your niece with chemo” and someone junior (and thus fireable) in the office learns that they don’t have a niece with cancer? Knowing a secret your boss doesn’t want to get out makes for a tenable position.

        1. Grits McGee*

          Or discovering that your boss has been living under another man’s stolen identity since the Korean War? :)

          1. Falling Diphthong*

            Yeah, that! You can’t be sure the revelation is going to garner “This is a grave violation of the trust we placed in Don!” versus “Who cares?” But if your boss knows you know, that he knows that you know he knows… makes for a tense office.

            1. Allison*

              Do I see references to Mad Man AND Friends in one comment? . . . I like you.

    3. Lilo*

      Agreed. I have never cheated on my spouse but I can’t think if the last time, if ever, I have felt the need to say that to anyone at work. That is just not appropriate work conversation because it naturally seems part of a somewhat accusatory conversation where either the other person feels they have to overstate or the implication is that they don’t have that same kind of relationships. In the same way someone else’s open relationship is none of my business, someone’s monogamy is as well.

      1. MegaMoose, Esq*

        One of my favorite threads of the last few months was the “my coworker wants us to call her partner her master” because of the really thoughtful discussion of where those lines of appropriate work sharing lie. I think the general sense was that relationship status is appropriate, but details of your sexual life was not. There’s an interesting bit of grey area here where I think it’s okay to mention if you’re in a committed relationship with more than one person, but not okay to mention your open marriage.

        1. TL -*

          Well, if I’m single and mentioning my many conquests and one night stands, that’s inappropriate, but mentioning my partner isn’t, even if we’re not super serious.
          I think it’s the same thing – if I have multiple significant others, than mentioning them is okay, even if they’re varying levels of serious. Mentioning that my wife doesn’t mind what I do as long as it’s in a different area code is much closer to one night stands than “this is my husband John and boyfriend Little John.”

          1. MegaMoose, Esq*

            Yeah, that was pretty much what I was getting at. Other people put it much more succinctly.

          2. Lilo*

            I think there is a reasonable difference between someone who has multiple commited partners and someone who has multiple sex partners but they aren’t part of polyamory. Someone who is a more serious partner and naturally comes into activities outside of someone’s sex life. Whereas an announcement of monogamy or someone’s sex partners is naturally an announcement about someone’s sex life particularly. It’s the difference between “this is my girlfriend” and saying “boy am I heterosexual. Just love straight sex”. Sure one may be implied by the other, but there’s a difference in taking it to the sexual.

            1. SarahTheEntwife*

              That does make it weirdly difficult to be out as bisexual if you’re in a monogamous relationship. Everyone assumes I’m straight because I’m dating a guy, and at some level coming out as bi really does mean telling them otherwise-irrelevant information about my sex life. But in another sense it’s something of a political statement independent of what individual people I’m attracted to or sleeping with.

              2. Zombii*

                Being out as anything at any time is considered overshare by the people who can’t hear a discussion about gender and/or sexuality without imagining The Sex. One day we’ll be past it but right now it’s frustrating as hell.

      3. TootsNYC*

        I agree, specifically saying, “I’d never cheat” is a red flag. It means it HAS crossed your mind.

        However, I worked with a man who frequently mentioned his wife in an indulgent tone, and once or twice said, “I have a great wife.” That’s a different thing.

        2. mcr-red*

          Yeah do you know who loudly proclaimed an awful lot, “I’d never cheat! I could never do that, I’d be honest and just end the relationship” – my ex. Want to guess why we divorced?

          1. Zombii*

            Because he was so honest he decided to end the relationship instead of cheat? jk :(

            I’m sorry. I’ve been in similar places.

    4. SignalLost*

      Yup. I had to lecture my nephew this week that no one would have thought twice about $Thing if he hadn’t announced that “honestly, he didn’t do $Thing,” which made us all aware that a) he had done $Thing and b) was lying. If you lead with how honest you are or what you don’t do or whatever, you’re lying. If you don’t lie, you don’t tell people how honest you are all the time, you just keep on not lying!

      1. Rookie Manager*

        The only time you knew my Grandad was telling the truth was was he included “honest” in the sentence*. The rest of the time it couls be a tall tale/joke/story.
        However he was a unique and wonderful man who didn’t follow all the normal rules.

        *Integrity was incredibly important to him but he wouldn’t want the truth to get in the way of a good story. I believe this was his internal compromise.

        2. Bryce*

          I follow a similar philosophy. Though I’m not a habitual prankster or anything, the biggest sin in my mind is flat-out telling someone “this is not a joke” or “I’m not in on the prank” when you are.

    6. K.*

      Yep. The people who loudly proclaim “I WOULD NEVER” apropos of nothing are almost certainly doing that thing in secret.

      Decide if you can live with this knowledge, OP. If you can’t, start looking. If you can, keep doing your job as though nothing happened. If you do decide to leave, don’t let it be known that this is the reason. Keep it between you and your journal no matter what you decide to do.

    7. Callalily*

      I remember my first boyfriend went on a loud tirade when we first met about how much he despised men who beat women, how much he respected women, and how he’d never hurt a fly.

      A couple of years after that he progressively beat me to the point that he had pinned me down (choking me) on the bed and threw me backwards through a glass door.

      The louder/more vocal they are about their values, the worse they probably are.

    8. So very anon*

      Yep. I actually did a little sex work at one point. A “sugar baby” situation for a short time.

      The guy was vocally Christian, married with kids, ran all kinds of stuff at his church and a children’s group that was like boy scouts but super religious. Very traditional “pillar of the community” type.

      1. therewithya!*

        SAME HERE! Look, someone’s payin for it or there wouldn’t be an industry… And the pillar of the community types have more access to funds to enjoy said behaviors.
        When I worked in phone sex there were so many guys who would say that they loved their wives… but they didn’t understand them sexually. So to them it was ok to cheat, because it was just sex… not emotional attachment.

          2. therewithya!*

            Other than the original kink, most of what I did was listened and responded to keep the convo going. Honestly, almost all of these guys would talk to me in depth about their personal lives- and a multitude of them were community pillar types. Heck I once had a 4 hour convo about The New Deal with a client on his dime.
            But other than the phone sex I also had a sugar daddy or three in my time…. That was frequently their justification for their behavior, too. It’s the “She doesn’t understand me” trope.

        2. Annonymouse*

          I can kind of understand though if the guy is into something and his wife/girlfriend has made it clear she is not or just not into sex in general that he would try a sex line.

          It’s all talk, no emotion and it makes him happy so I’m more ok with that than cheating or escorts.

      2. anon for this*

        I used to sell adult toys. Our sales reps kept getting what were essentially prank calls from one particular person. He would contact a representative, request to special order a specific item while giving an implausible excuse for why he ‘needed’ it, and then never provided payment information and stopped responding to calls or emails. Eventually he’d move on to another sales rep and start the schtick all over again. It was pretty frustrating to realize that he just enjoyed the thrill of talking about this item, and didn’t care that he was wasting our time or that we’re not free fantasy hotline operators.

        Eventually our customer service head googled him and discovered that he is, of course, a Kansas pastor. Founded his own church, in fact. She emailed the church’s address to ask where he would like the item shipped, and he finally responded by furiously telling her to leave him alone. She replied, sweet-as-pie, “thank you for your interest in [company]! If you have any need for our products please contact me directly at the customer care office!”

          1. anon for this*

            Sadly, no, but there were aaaallll kinds of other stories like that. People would pass on warnings about creepy customers repeatedly asking for something that’s against our rules. After a long back-and-forth, the sales rep always told them no, and they’d contact another person and start all over. They kind of took on legendary status after doing this a few times. When one of them tried it on me, it was like meeting a unicorn!

    9. Troutwaxer*

      Sort of like how people who repeatedly tell you “I’m a nice guy” seldom are.

      “Don’t worry hon, I’m a complete asshole!”

    11. Blaine*

      Anyone that has to tell you what they are simply are not that. Those who say “I’m not dramatic but…”

      Also in this red flag cheating category are the ones that constantly accuse you of cheating, or question where you are, who you are with, etc. I think of it as hyper aware projected accusations.

  5. The Not Mad But Occasionally Irritable Scientist*

    I’m beginning to think that global warming is actually caused by egregiously insane workplace behavior, because OH MY GOD ALISON THE STORIES YOU ARE RUNNING LATELY.

        1. Djuna*

          The past few months on here have really made me move my mental goalposts on “what really is batcrap doolally in the workplace”.

          Apart from being downright entertaining, it’s given me much-needed perspective on totally normal workplace annoyances that were beginning to weigh unduly heavily on me.

          Well, that and a brief vacation which was (in retrospect) very overdue.

      3. Pennalynn Lott*

        I have been away from AAM for a few months, because school was kicking my butt this past semester, but the OP and this comment are why I will never ever give up AAM entirely. :-D

    5. Karen D*

      I believe AAM is seriously gaining traction, thanks to Alison’s hard work across multiple platforms, and sound advice. (I know she’s been mentioned as a great alternative to many who are not entirely happy with the new Dear Prudence.) The more people know who she is, the bigger variety of questions she’s going to get.

      1. The Not Mad But Occasionally Irritable Scientist*

        Funny, I absolutely love both Alison’s advice and Mallory Ortberg’s. Mallory’s writing is hysterical and I love the dry, literary wit, but that wouldn’t be as appropriate for workplace advice as Alison’s.

        1. Karen D*

          I adore her writing … but sometimes I deplore her advice. Alison’s feet are far more firmly on the ground.

        2. VP*

          Agreed. Ortberg > Yoffe.

          I have a theory that AAM, Captain Awkward, the new Prudence, and the Bad Advisor at the Establishment are all descendants of Carolyn Hax.

          1. Ask a Manager* Post author

            I think I owe a huge part of my worldview to Hax; I started reading her with her very first column when I was pretty young, and she has had an enormous influence on how I think (especially about romantic relationships, but it all translates).

            1. VP*

              I am delighted by this because it confirms my suspicion (I used to be a print culture researcher–still got it) and also because Hax basically raised me in syndication.

              1. Ask a Manager* Post author

                I’m dying to hear more about this. What is a print culture researcher? And how did you put together all the bread crumbs to figure this out?

                1. VP*

                  “Print culture researcher” is just a concise way of saying “academic in literature whose research specialization included print culture (an umbrella term for magazines, newspapers, pamphlets, ads, etc. and now also includes electronic versions of all those things + blogs and social media–basically anything ‘media’ that involves text).” I hesitate to go too much further into detail here because it would make me pretty easily identifiable, even by a Google search (not many people do what I did). I loved it; sadly, academia isn’t exactly rushing to support humanities research these days.

                  Advice columns have a long and really interesting history. It’s been sort of a hobby project of mine to keep track of them and look for patterns. They’re having a bit of a moment right now–suddenly reading advice columns is a cool millennial thing to do! Someday I’m going to write an article about them and pitch it somewhere. When Carolyn Hax first started, she was marketed as an alternative to Ann Landers et al. because of her ruthless humanism and careful balance of post-90s snarky humor and compassion; advice columns that have blown up more recently seem to be modeled after her. Key words like “boundaries”; the idea that it doesn’t matter what other people *should* do because you can’t make others do anything and that communication is best if simple, direct, and unfailingly honest. (You’re also all from New England–not sure what that has to do with anything yet, but it’s weirdly common for writing styles and influences to naturally group themselves together by region. The writing world is small.)

                2. Ask a Manager* Post author

                  That’s fascinating. I’m actually not from New England, but both my parents are and I know that’s influenced me.

                  If you’d be interested to talk more, I’d love to do some kind of chat with you that I could print here. I’d protect your anonymity! Email me if you’d be up for it (but no pressure if you’re not; I’d totally understand if you wanted to save it all for your article!).

            2. tigerStripes*

              Alison, you and Carolyn Hax are my favorite columnists because you are both so thorough and practical and you both just make sense, which is not something that can be said about some columnists.

              I also appreciate the way you acknowledge it if you make a mistake.

        3. Elizabeth H.*

          I think she gives bad advice sometimes. I was especially annoyed by her advice to the guy who accidentally slammed his girlfriend’s kid’s hand in a car door, felt terrible about it and also felt weird about the way his girlfriend sent him the bill. It was so obvious to me that he was hurt by the formal/transactional way she was framing the incident rather than because he felt like he shouldn’t have to pay for it and Mallory was totally oblivious to that aspect of what he was saying. I eventually stopped reading, I miss Emily Yoffe.

          1. JB (not in Houston)*

            I adore Mallory, but I do think she misses what the LWs are saying sometimes, and that results in her giving bad advice.

            1. Countess Boochie Flagrante*

              Yeah, agreed.

              Though, to be honest, I’ll take that over Yoffe occasionally getting really gross and judgy about things.

              1. Marillenbaum*

                THIS. If I never have to hear Emily Yoffe defending rape culture and mocking consent again, I will be a happy human.

                1. Elizabeth H.*

                  I actually agree with Emily Yoffe’s views on that stuff, not everyone has the same opinions on that kind of thing.

          2. Lissa*

            Yeah, I really liked Mallory Ortberg’s writing and her advice is often quite good, but every so often she latches onto one aspect and decides she knows the inner workings of somebody’s character, so it feels like shaking her fist “you are a bad person for having these thoughts!” rather than actual advice. Another was the lecture she gave to the woman who gave a treasured family heirloom related to a baby to somebody who’s baby died, and wanted the heirloom back but the woman wanted to burn it. One can have compassion for more than one person at once in a situation!

            1. Kbug*

              Definitely- I also just read an advice column on Ravishly that prompted me to write to the editors and explain how dangerous and incompetent their advice was to people who had been abused. I come to AAM for practicality, and because Alison isn’t afraid to ask for opinions or retract something if she finds she’s off base.

            2. Elizabeth H.*

              Oh yeah, I just remembered that the last straw for me was the podcast where someone wrote in about how she couldn’t stop stalking behavior toward this guy and she felt like she was out of control and paralyzed with guilt and shame about it, and instead of being compassionate and giving her useful advice, Mallory Ortberg just went on berating her about how crazy and unacceptable and practically criminal her behavior was and needed to stop, and was practically mocking her about it. Like she just repeated back the letter writer’s problem back to her, it was totally unhelpful and even cruel. That really bothered me.

      2. Mephyle*

        I like the way Mallory doesn’t mince words if an LW’s situation or partner is untenable. More than any other relationship columnist I can think of, she will be open about her horror that LW is considering doing anything but running away far and fast.

        1. seejay*

          don’t read the FB responses to her posts then… most people there get butthurt over the idea that Mallory advises leaving pretty quick. When I feel like jabbing myself in the face with a pen, I go read the commentary there and it’s usually pretty horrible, with a lot of people crapping all over the advice about “WHY DO YOU HATE RELATIONSHIPS SO MUCH AND TELL PEOPLE TO LEAVE THEIR SPOUSE/PARTNER SO FAST????”

          Duh, maybe because it’s bad?

          1. Countess Boochie Flagrante*

            Captain Awkward used to get a lot of that — I think it’s gotten to the point now where her regular readers are pretty comfortable with the notion that it isn’t that she hates relationships, it’s that the relationships people write in to her about are pretty terrible.

            Come to think of it, it’s a lot like the way a lot of Alison’s advice here ends up being “you can learn to deal with this or you can ollie outie of this job.”

            1. seejay*

              When I started reading CA, what struck me was how 95% of the letters to her were about relationships or situations that were at the point where they were so far gone, they weren’t salvageable… so yeah, the advice is going to be “GET OUT, DO NOT PASS GO” with maybe the caveat of “stick around if you need to set up a plan first”. At least half of Mallory’s letters usually aren’t as dire.

              Reading CA sometimes is like watching a train on fire, hurtling towards a train loaded with nuclear waste, and both of them are riding a rickety wooden bridge over a TNT plant. :(

            2. alter_ego*

              I think with a lot of advice columns, the issue is that people are basically writing in to ask “how can I change my parents/partners/bosses behavior?” And because the answer is “you can’t” the only response the columnist can give is to learn to deal with it or leave. If the parent/partner/boss wrote in to say “I think I’m behaving poorly, what do I do?” then there’s some concrete steps that can be given. But since we’re normally not talking to the person with the power to make the necessary changes, then deal with it or leave ends up being the only thing under the letter writer’s control.

              1. filmgal*

                I think you’re right! Like 50% of the letters here on AAM I’m like, “girl, get out!” when reading them. Really we all have to protect ourselves to some degree, because nobody else will do it for us. That means removing ourselves from untenable situations, and being okay with that decision.

                Unfortunately, people are often scared of doing that for any number of reasons and stack them all up when writing in to an advice columnist. It’s pretty clear to everybody but the letter writer themselves that they should get out and they just need an impartial observer to confirm their suspicions.

                1. Annonymouse*

                  The way I always framed it is imagine your at a circus on a tightrope walking platform – no one knows how you ended up there but you’re there now.

                  The platform is tiny but you’re ok.

                  You can’t get down but across the rope there is a bigger platform and a way down.

                  The only problem is the long tightrope between the platforms with no net or balance pole.

                  You can stay where you are or try to make a break for it and might not succeed.

                  Some people convince themselves that tiny platform is fine and stay there unhappily.

                  Others realise this isn’t good but are too scared to take the steps to get somewhere better.

                  Some start but the reaction of the crowd makes them turn back.

                  And the last people are determined to get out come hell or high water.

      3. GermanGirl*

        I actually came here through an answer at workplace.stackexchange.com, where someone quoted and linked advice from here.

  6. MegaMoose, Esq*

    Oof, I can see why the LW is unsettled by this. That said, I wouldn’t really call this conspicuous. Certainly it was easy for the LW to track down what was going on, given her access to his email, but there were still a couple of steps involved. I guess I see this as living in the middle ground between conspicuous and perfectly discrete – how many people would have cause to go through his sent messages in the first place, and of them, how many would have the reason or inclination to google random meetings he’s set up? I agree with Alison on this one – let it go, especially since you’re planning on heading out anyhow.

    1. LBK*

      The OP definitely has evidence that others wouldn’t have access to, but he’s going to meet them during work hours, and that’s not particularly conspicuous. All it takes is for some colleague to happen to spot him at a hotel rather than wherever he claims he’s going and things could fall apart pretty fast from there.

      1. Princess Consuela Banana Hammock*

        Wait, do y’all mean inconspicuous? Because conspicuous means “standing out to be clearly visible” or “attracting attention.”

        1. Princess Consuela Banana Hammock*

          (By y’all I meant LBK—apologies for my (incorrect) fast typing).

              1. Karen D*

                You and me both! (passes over one of those little bottles packed with super-concentrated go juice.)

      2. MegaMoose, Esq*

        I don’t think he’s being as discrete as he could be, I’m just saying I could think of a LOT more conspicuous ways to be having an affair here. Like the executive whose emails I reviewed late last year who exchanged nude pictures with his mistress via work email, for example.

        1. Princess Consuela Banana Hammock*

          People never fail to astound me with their stupidity.

          I agree with you—he’s not being as discreet as he could. But I also don’t think he’s being conspicuous enough for OP to say/do anything about it, absent some demonstration of theft.

        2. Jessesgirl72*

          Or the OP from not long ago who was asking his AA to lie to his wife and mistresses for him-who got caught spectacularly in the update.

        3. Liane*

          I think this is what OP is concerned about–that if she can find this relatively easily, Company IT, or a lawyer such as yourself, could find it even easier if Grandboss or Wife asks.

          Now I also think LW is letting her curiosity get the better of her. While that is understandable, it should be reined in. Deciding this is Yet Another Reason to job hunt, however–go for it and good luck.

          1. MegaMoose, Esq*

            Oh yeah, if anyone had a reason to go looking, this would be super easy to track down. That’s on the boss, though, not the OP.

            This reminds me of the time my spouse got into a fairly contentious debate with a guy online who had linked his accounts in such a way that my spouse could have easily doxed this individual. My spouse tried to play good Samaritan and warn the guy about it, but dude was not receptive and just got more aggressive. No good deed, etc etc.

        4. Gov Worker*

          Why would anyone think a work email server is in any way private? I barely think my personal email is private. So foolish, but maybe this guy is an exhibitionist.

          That said, MYOB is generally a good policy to follow in the workplace.

          1. Karen D*

            People who do this are depending on herd anonymity. It never seems to occur to them that there might be a time when someone is specifically scrutinizing their history.

          2. Falling Diphthong*

            I think there is a powerful will to believe “If I want to be invisible, and I don’t see anyone, then I am” that people haven’t managed to adept fluently to technology. Or when they do, it doesn’t generate any stories and so goes unremarked. Anything that needs a password, people think of as obviously extra secure and private.

          3. Princess Consuela Banana Hammock*

            You know how small children think that if they can’t see you (e.g., when playing peek-a-boo), that you can’t see them, either? It’s like that.

          4. Anon for this*

            Everyone forgets. Years ago an exec at a former employer had to read a bunch of archived IMs before he was deposed. The next week every department head gave their teams mandatory lectures about appropriate business communication and company retention policies. So many poop jokes.

        5. Stephanie*

          Yeah, it’s work email for one thing–I don’t really have an expectation of privacy in my work email. I mean, everywhere I’ve worked I’ve never expected IT to read my emails without some cause (as my friend’s husband who works in IT once put it: “Your emails are too many in number and too boring for us to read without some probable cause.”), but I’ve never expected privacy since the email is there to help the company make money. And furthermore…he has an EA who has access to his email. He definitely isn’t hiding it that well.

    2. Princess Carolyn*

      The conspicuous part, I think, is that these escorts presumably receive emails from, like, randy.smith@companyname dot com. That effectively ties to the company to something it likely wants nothing to do with. If, for some reason, this ever becomes public knowledge, the company’s name will be involved.

      1. MegaMoose, Esq*

        Yeah, but this kind of junk happens all the time and is rarely of public interest. I don’t think the possibility of the company’s name being connected to this creates a moral duty for the LW to intervene.

        1. Elizabeth the Ginger*

          Yeah – unless his career is about morality (he’s an editor for an evangelical publication, say, or he’s a politician running on “family values”) then it’s unlikely to matter.

    3. paul*

      Yeah that’s about where I’m falling. And I’m honestly kind of wondering why OP felt like digging through this gunk? It doesn’t seem to impacting the workplace?

      1. Princess Consuela Banana Hammock*

        Agreed. The first round of googling makes sense in light of OP’s EA responsibilities. All the other googling sounds like it was just salacious curiosity.

        1. MegaMoose, Esq*

          And hey, I’m not going to condemn salacious curiosity, but I do think it’s best not to act on anything one finds out once one is clearly into that territory.

          1. Marillenbaum*

            This is definitely one of those things where if you’re going to be nosy (and God knows, I can be nosy), be discreetly nosy, keep it to yourself, and if the **** ever hits the fan, keep being discreet while secretly embodying that GIF of Michael Jackson eating popcorn from the “Thriller” video.

            1. Lissa*

              That is me, so often. I’ve gotten a lot better but I can be really really nosy and good at finding things out without really trying. So I have had to learn the skill of just keeping that to myself and venting to my best friend who lives 1000 miles away.

          2. Anna*

            Yep! Unless someone is in danger, or the boss is stealing money from the company, or some other incredibly bad thing is happening, there’s no need for it to go any further than the OP.

    4. Falling Diphthong*

      Eh, I think he’s reasoning “I use my work email, which only I have access to” which has the potential to knock him over with a feather when he realizes “I” = “I, my assistant, the entire IT department, my boss, the auditors, and the admin who knows that backdoor trick.”

      1. MegaMoose, Esq*

        Don’t forget the lawyers! And trust me, document review is boring, and we are laughing at you about anything weird that goes through your work email. Bwahahahahahahahaha!

        1. Countess Boochie Flagrante*

          Most important lesson of the working world: knowing anything you put on the company system can be demanded for legal purposes. Never editorialize. A few bosses ago, I had one who was our specialist for whenever payment disputes came up in court. She was not amused when notes including “the client ought to know that most grapes are not, in fact, purple!” had to be aired to attorneys.

        2. Nabby*

          My favorite example of this was the guy who was using company money to send the same jewelry/flowers/etc to his wife . . . and his girlfriend.

  7. Not Who I Think I Am*

    Please stop googling his emails. I’m pretty sure he would be sorely pissed if he found out. IMO, it’s way outside the scope of your job. Both of you will be happier.

    1. The Not Mad But Occasionally Irritable Scientist*

      Of course he would be sorely pissed, but….if you’re crowing to all and sundry, unforced, how you’re this great upstanding man with an awesome marriage and you would never cheat on your perfect spouse, and you give your assistant access to the same email you use for sex worker appointments, you’re either sabotaging the plans of your own Death Star or you’re a goddamn idiot.

        1. Falling Diphthong*

          … No, no, I want it to be the Death Star one. And he’s going to bring down the entire corrupt company via the just barely covered up, but not really, meetings with IRS agents disguised as escorts. He’s Barney Stinson.

      2. Princess Consuela Banana Hammock*

        Except OP had to do some digging to figure out these were sex workers. I agree that the crowing out is usually a signal that a person is doing exactly what they brag about not doing (as Alison notes, above). That said, the text of the emails don’t scream “I’M SCHEDULING A QUICKIE WITH A SEX WORKER!” They indicate that he’s setting up an appointment with someone, anyone.

        Not saying he’s not an idiot. Just saying it’s not super obvious that he’s up to no good.

        1. The Not Mad But Occasionally Irritable Scientist*

          Yeah, but setting up brief meetings in the middle of the day with strange gmail accounts, or”meeting a recruit” that never gets hired at a nearby hotel instead of in the office where most actual interviews get conducted, is not something people do unless they’re buying drugs or sexy times. And valid midday business meetings usually get put in the calendar as what they are, with business accounts for attendees displayed and usually an agenda or something. So I think it’s pretty obvious that he’s concealing what he’s doing, which begs the question.

          1. Princess Consuela Banana Hammock*

            Oh, I’m not saying he’s not dumb. And he’s certainly not being as discreet or careful as he thinks he is. But I think you’re assuming some things we don’t really know about (e.g., my calendar doesn’t provide business accounts, attendees and agendas for 90% of my meetings, we don’t know where he’s meeting these women, we don’t know if he’s booked these sessions on his calendar at all).

            He’s certainly going to get caught, eventually. But if I were OP, I’d steer as clear as possible in the meantime. OP doesn’t want to get swept up in whatever net or undertow he creates when all of this hits the fan.

            1. Gadfly*

              I wonder if it is too late to avoid being caught up in this if it all goes south… Is there a risk for the OP to know and not have brought it to someone’s attention if it does become an issue?

          2. Lilo*

            I agree with PCBH, boss is being dumb but LW googled email addresses which, without a work reason like she needed to get in touch with them, seems invasive. I understand the curiosity but I think it was a bad idea and potentially something punishable. LW really shouldn’t bring this up at all. I do think a possible action would be discipline against LW.

            1. Stellaaaaa*

              It’s completely reasonable for an executive assistant to look up people who emailed about supposedly work-related meetings but then never showed up to the office.

              That said, I don’t like to come down on people for locating information that is publicly available on the internet.

              1. Lilo*

                Even if LW was following policy, there’s a way to spin it badly and you can see an embarrassed boss or someone protecting him spinning fault in that manner. LW should steer clear.

                1. Stellaaaaa*

                  I have mixed feelings about what I think OP should do, but I definitely don’t think we should shame her or act like she’s skeevy or slimy for using freaking Google. She can google anything she wants.

                2. Princess Consuela Banana Hammock*

                  I agree with you, Stellaaaaa, but I also think OP should steer clear from now on. When this all hits the fan—and it will—it’s going to be valuable/important to be able to say truthfully that OP had no idea what was going on.

                4. Princess Consuela Banana Hammock*

                  @Emi. She knows what happened to date, but she can avoid knowing what happens going forward.

              2. JB (not in Houston)*

                I disagree, though. He didn’t ask her to follow up, didn’t complain about missing meetings, didn’t give her any reason why she needed to worry about it. She googled because she was curious.

                1. Stellaaaaa*

                  And that’s no crime. There is absolutely nothing wrong with googling literally any non-private information that has been published to the web. I can sit here and google Alison, your username, my sister’s boss, and the third cutest guy on Silicon Valley. In all seriousness, my coworkers and I sometimes google the email addresses and names in our work emails. We like to see what people look like.

                  As for the escorts, they’re posting ads on the Internet. OP is googling them, not inflicting anything on her boss.

            2. Sans*

              That’s what I’m thinking. Although she investigated the email addresses for an understandable reason, a defensive boss’ reaction might be to focus on her “snooping”. See no evil, hear no evil, speak no evil. It’s his life to screw up if he wants.

          3. neverjaunty*

            There can be lots of reasons that have nothing to do with escorts – for example, if he’s recruiting a high-level employee who needs to keep their job search confidential. Or if he’s meeting with a lawyer to discuss his age-discrimination lawsuit. Or if he’s a whistleblower.

            He may be stupidly indiscreet, but the indiscretion here is not blatant or gross. He just has an assistant who’s frankly being nosy.

            1. Karen D*

              No, the clandestine contacts are routinely turning up in Google searches as escorts. OP knows they are escorts.

              1. Beezus*

                Right, but she only knows that because she’s Googling, which she has no business doing, because of all the appropriate reasons for clandestine meetings that neverjaunty listed.

              2. Zombii*

                I may have misread the threading but I thought neverjaunty was responding to the accusation that the only possible explanation for Boss’s behavior was sex or drugs by listing other potential explanations.

                1. neverjaunty*

                  Correct. We know they’re escorts, but “nobody does this stuff unless they’re hiring escorts!” isn’t true.

            2. Falling Diphthong*

              If you want privacy, your philosophy shouldn’t be “Stuff that will pass just fine so long as I never encounter anyone nosy. Or curious. Or more technology savvy then myself.”

              1. Amy G. Golly*

                More than one person can be wrong in any given scenario. Is it more wrong that this dude is scheduling sex workers with his work account? Which his assistant has access to? And then loudly bragging to the entire office about how “faithful” he is? Yes. That is the most wrong.

                But still wrong is digging through your boss’s sent emails and googling his contacts. It’s not your business, you won’t be able to do anything about it, and it’ll only come back to bite you if, down the line, he does get in trouble for his indiscretions and someone comes asking about what you knew, when, and how.

                2. Not Who I Think I Am*

                  This. The boss might be a greaseball, but he didn’t write to AAM for feedback.

            3. GermanGirl*

              Or it is not cheating because his wife knows and is ok with it (it’s a threesome or he has preferences that she doesn’t share but she’s fine with him getting that from someone else).

              Anyway, I’d say it’s none of OPs business unless … well OP said it’s on company time and on the same hotel account as his business trips.

              Now “on company time” might not be an issue here because he’s likely to have a somewhat flexible contract so taking an extra long break might be a non issue as long as he gets his work done.

              And even the hotel account might be his private one that he happens to also use for company travel in order to collect the bonuses, which can be fine if he bills the company correctly and declares the bonus in his taxes.

              So unless OP knows that none of this is the case, there is no reason for her to do anything about it.

              1. Jessie the First (or second)*

                This is not really how US employment works – “he’s likely to have a somewhat flexible contract so taking an extra long break might be a non issue as long as he gets his work done.”

                He probably does not have a contract – a lot of US workers have no contract in office jobs. He is not going to have time he has to be at his desk vs time he is allotted for breaks: his schedule is his to manage. That gives him flexibility to his schedule that perhaps is not the norm for you. He won’t be “on company time” in the sense you are thinking (though the disadvantage there is that he will be expected to work or answer calls or emails at any time, most likely – if something pops up at 9 pm on a Sunday, he’ll need to respond).

                “declares the bonus in his taxes.” – If the LW was referring to rewards points at hotels, there is nothing to declare. There is no cash bonus. It’s just basically a discount on the hotel price. Not a tax issue.

                So, if he pops out midday for lunch, a haircut, a nice walk in the sun, a trip to visit his son’s teacher for a school conference, or head to a hotel room for mid-day sex, it does not really matter in terms of “company time.” Non-issue, really.

    2. k*

      I would stop looking into it, but for other reasons. If you don’t look them up, it gives you plausible deniability if this ever blows up.

    3. Yellow*

      Yep, this. The above scenario, among so many other pieces of information I’ve accidentally tripped across as an EA, fall squarely into the category of Not My Business/Problem and do not affect my job. I waste no energy or time on things that have nothing to do with my responsibilities and do not harm my fellow coworkers.

  8. Cambridge Comma*

    OP, I think that as long as you have plausible deniability you’re in the clear, and you really do. You had to be pretty ingenious to figure it out — he’s not as conspicuous as you think he is.
    Its also nice to have yet another proof that when people go around trumpeting their extreme morality on a certain issue, it is a huge flashing arrow that this is the temptation they are fighting against. Although I wonder if he justifies it to himself in some way, for example by saying it’s not the same as having an affair.

  9. The Not Mad But Occasionally Irritable Scientist*

    As for how to handle this? Find another job. Then, when you give notice, go “Oh, and by the way? Gmail has free accounts. Accounts I do not have access to. Accounts you do not USE FOR PERSONAL BUSINESS AM I MAKING MYSELF CLEAR.”

    1. EddieSherbert*

      Yes. Hahaha.

      This is literally the only way it’s even plausible to bring it up to him (and even then I’d be iffy since I guess he could give a bad reference in the future… for telling him his affairs were kind of obvious to you…).

      1. Falling Diphthong*

        Also, while I’m not quite sure what this hotel account is, surely the secret meetings with your mistresses should be held under another credit card? I get it, points, but if you’re trying to be discreet…

        1. Yorick*

          Maybe it is a hotel rewards account that is not linked to a particular credit card?

        2. The Not Mad But Occasionally Irritable Scientist*

          It might blow up my marriage and get me fired, but I almost have $100 bucks in Amazon points and that massaging office chair ain’t buyin’ itself, honey.

        3. I totally don't know anything about this*

          The proper protocol is to give her the money and have her book the room.

  10. Kristine*

    “Never even had a fleeting thought of being adulterous.” Ah, the Icky Office Overshare That Conceals Hypocrisy (TM). Back away.

      1. Hermione*

        SO and I do, too. “Why hellllooooo, Chris Hemsworth. Please do come in…”

        (Pun definitely intended…)

          2. Lily Rowan*

            Also Justin Theroux, and don’t think that’s not confusing in my head sometimes!

                2. JessaB*

                  Lily I’m surprised you’re not all over Toots for tryin to mack on your man.

          3. Karen D*

            Yeah, there are some days when my list basically IS Justin Trudeau.

            Also: Any of the Chrises. Except Bale, who never seems to end up on Chris Lists anyway, probably because he just seems so grumpy and non-fun. And Pratt because he and Anna Faris are a steady stream of light bringing joy to all who behold them, and who wants to mess with that? (But otherwise: TOTALLY Pratt.)

            1. AMPG*

              Did you see SNL this week? The “Not That Chris” song with Chris Pine was really funny. Also, I love Chris Pine’s singing voice, and they had him singing in almost every sketch.

        2. Lentils*

          Hah, my wife and I have basically the same taste in women so we’ve agreed that we’d just share. We disagree on some men though; she’s a long-time True Blood fan who loves Alexander Skarsgård, and I do not, so I tell her she’s welcome to him and I hope they have a good time lol.

          1. JessaB*

            Any Skarsgård up to and including dad Stellan. That familly is amazingly good looking. So, if you’re into it (I am also) are the daughters.

    2. Bryce*

      I’ve never understood that turn of phrase. Of course I’ve thought about it, how else could I reject the idea? “Never even crossed my mind” is, to me, the sign of a liar or lacking imagination.

      1. Consumer*

        I agree! I only use that phrase when something never occurred to me. For example, my husband pointed out a super easy fix for a problem…hours after I’d used a difficult, convoluted, time consuming solution. Never even crossed my mind to go the easier route. I wish it had!

  11. TL -*

    Also seconding that it’s weird to know your boss’ stance on fidelity unless he’s a pastor or marriage counselor. Most people think lying to your partner is generally bad.
    Though my guess is the boss thinks every man cheats on his wife.

    1. Gandalf the Nude*

      This part wasn’t actually that weird to me. My boss and I also have a good rapport and frequently chat current events. The times adultery has come up , he usually expresses his befuddlement that A) cheaters are so callous and B) these cheaters are careless enough to get caught. And if applicable, he follows up with shock that a fellow Christian would do such a thing. Sometimes the struggle to not roll my eyes becomes physically painful, but it still doesn’t feel like an especially strange conversation.

      1. Parenthetically*

        It seems like the boss in this scenario is making pronouncements out of the blue, whereas I think it’s natural to ruminate on adultery if it comes up in conversation.

      2. Jake*

        That has been my exact thought when reading these comments. In fact, I’ve probably made a statement that I’ve never cheated on my wife while talking to coworkers and even a subordinate, however, it was definitely in the context of discussing adultery already.

        Proclamations out of the blue would be weird though.

    2. Countess Boochie Flagrante*

      Either that or the boss thinks that seeing professionals doesn’t constitute cheating.

  12. Norv*

    Seems to me that she is taking a LOT of extra steps in finding out who belongs to these emails addresses. Maybe sticking to the task at hand might be the way to go.

    1. Cambridge Comma*

      I don’t know, it seems pretty reasonable how she found the first one, she googled the address for a task-related reason and from there on in it’s a single step.

    2. EA*

      I don’t think she is going out of her way.

      I google everything on my bosses calendar or his email. I am expected to anticipate needs/find mistakes before they happen, and being sort of nosy is a way I have found to do that.

      1. Havarti*

        Alas, being nosy is how you survive being an important person’s helper. I’m pretty sure Little Red Riding Hood would look at me and declare, “Havarti, what long ears you have!” “All the better to hear with, my child.”

        2. Yellow*

          It is indeed how you survive being an Important Person’s Helper, but the other half of the job is using your judgement to know when something should be ignored and is not relevant or is not pertinent to your job function.

      2. Manders*

        Yep, this is pretty much normal for executive assistants. If you truly don’t want your EA finding out what you do, 1) don’t do it during working hours and 2) don’t involve any email account or hotel account the EA has access to, because reviewing these things to make sure everything’s accurate and nothing important slips through the cracks is their job.

        1. INFJ*

          Yeah, never mind googling the email: she has access to the records of him actually booking a hotel room during the time he said that he was just on a work meeting.

      3. Shadow*

        The first time yes, but she’s continuing to open emails from that account and google the recipient

        1. Manders*

          Since the hotel account’s involved, she may have to keep doing some basic checks to make sure that her boss booked the room on purpose and wasn’t billed in error. Random hour-long bookings of hotel time in the middle of a workday, at a time the boss told the EA he wasn’t planning to book a room, would definitely be an issue the EA needs to check.

          1. neverjaunty*

            The OP said explicitly in her letter than she Googled the first time because she wanted to know if it was a recruiting candidate. There was nothing whatsoever about having to look email addresses up to confirm hotels.

            1. Manders*

              If he’s leaving the office during work hours and saying he’s going to a meeting, she also may need to find out who she’s meeting with so she can make sure he has any relevant documents and information, or so she knows whether it’s ok to to interrupt him with a call if something urgent comes up.

              I know this feels a lot like snooping, but an EA needing to know where her boss is and what his meetings are about during the workday is totally normal.

              1. JB (not in Houston)*

                It seems like you are ignoring what she said in her letter and projecting your situation on hers.

        2. That Would Be a Good Band Name*

          I would also assume that she still needs to check each appointment in case it is something that she needs to plan for/place on his calendar. I’ve never been an admin, but doesn’t an admin pretty much run their boss’s email? At least that seems to have been how it’s handled where I’ve worked. So I can’t imagine why someone would do anything they didn’t want found out with any account that their EA would have access to.

          1. Elizabeth West*

            Yes, an EA definitely would. They screen all emails and handle the calendar, etc. If you’re sending email to a bigwig, their assistant sees it first.

  13. Snarkus Aurelius*

    You had to go out of your way to find out this was an escort service so, no, he’ s not being conspicuous. Conspicuous wouldn’t require a Google search nor would it give the initial impression of a recruiting candidate.

    Given that, I’m not sure what your point is in telling your boss other than to convey that you know. Of course, this behavior is risky, especially when it’s done on company time and resources. He’s doing it because it’s what he wants to not because he’s ignorant of the risks to his job and reputation. You can’t honestly think he’s unaware of the consequences?

    All in all, this is none of your business. I’d also ask that you stop Googling these email addresses as there’s no point. If nothing else, do you really want those search queries in your internet browsing history?

    2. The Not Mad But Occasionally Irritable Scientist*

      Conducting this kind of correspondence on a work email account shared with someone else, who you happen to brag to about your morals constantly, is pretty conspicuous. And c’mon, when a married guy is setting up meetings with “candidates” at hotels and setting up short, business hours meetings with non-business accounts with suggestive names, with no agenda, that’s raising PLENTY of flags that would make anybody suspicious.

    3. Morning Glory*

      There actually is a job-related reason to search email addresses, especially as related to emails discussing appointments. If the OP is expected to put appts on the boss’s calendar, then adding in the reason, or the company name, etc. is the best way to give a busy executive context. The assistant often has to dig for that information.

      Now that the OP knows about these specific kinds of emails, sure she should stop googling. But she wasn’t wrong to do it to begin with.

      1. tigerlily*

        Sure, but according to the OP, that’s not what happened here. She was looking for a specific sent email, found an unrelated email from someone she didn’t know and decided to google it. Then decided to keep digging when she discovered it was an escort.

        1. Morning Glory*

          I read the OP’s letter as, she googled the first email to see if it the recruiting candidate (if it was, that would likely be something she’d need to add to the exec’s schedule).

          The search after that on the premise of a possible hack… well it’s possible she was just being nosy at the point. But if he had been hacked, and she had seen a suspicious email and ignored it, that could have reflected poorly on her. It really depends on the workplace culture and the consequences of a security breach.

          1. MegaMoose, Esq*

            Yeah… I don’t want to get into giving the OP too hard of a time, but this is not what hacking looks like. Do people really think that people hijack email accounts just to send vague isolated emails (without actually locking out the original user)?

            1. Anna*

              To be fair, most people in the world don’t actually know what hacking looks like or there would be no reason for hackers to hack email accounts. Whether it was a flimsy excuse or not, people are given vague warnings about “emails you don’t recognize the address,” which is exactly what happened. Hacking is frequently an umbrella term used to cover a wide variety of illegal online activities.

              1. MegaMoose, Esq*

                Eh, you make a good point. If people were smarter about email security, certain corners of the world might be a very different place today.

              2. Emi.*

                Also, people often say “my account got hacked” to mean “my account was hit by malware that caused it to send out a bunch of spam.”

                1. Zombii*

                  Don’t forget “I use the same password for everything and it’s a really obvious password,” and “I left my account signed-in on a shared computer.” Hacking! ;P

    4. Lilo*

      Even if LW was following policy, there’s a way to spin it badly and you can see an embarrassed boss or someone protecting him spinning fault in that manner. LW should steer clear.

      1. Lilo*

        (I have no idea how this comment ended composting twice in different places. Sorry!)

        1. Minnesota*

          I just have to say that I love impact of what I presume was the auto correct here–idea of a composting comment, breaking down, mingling with the other comments in the composter, and ultimately being used to make the conversation richer. (Can you tell I have gardening on my mind today?)

  14. ArtsAdmin4Life*

    I agree – let it go. He’ll get caught one way or another if it’s a affair situation (i.e. not approved by his wife).

    The only thing about the letter that make me take some notice was this sentence ” I have access to his hotel account”. If the boss is using a company credit card to pay for the hotel, or is charging hotel rooms used for affairs to a company account, the LW would need to get HR and/or high-ups involved.

    1. Cambridge Comma*

      Good point. But couldn’t she query the hotel rooms specifically (e.g. ‘I’ve noticed a couple of bookings for days that I can see in your calendar you were in town, do you think there is something wrong with your account?’). That would probably put a stop to the behavior without having to talk about the e-mails.

      1. Princess Consuela Banana Hammock*

        Agreed. This was my only hesitation with the advice. Meeting people on company time is not great, but I can understand all the ways you can rationalize that you were meeting up while on your lunch break. But using company resources (aside from his email account) to do it could be a huge problem. I like Cambridge Comma’s script for how to raise the issue if Boss is in fact using his company account/card for hotel (or similar) reservations.

    2. MI Dawn*

      Yeah…I doubt the company is happily paying for him to use hotel rooms for non-business uses. On the other hand, if he’s using the company card but paying them back for the charges out of his own pocket, they might not care.

      1. Savannnah*

        You might be surprised as to what people can get away with in certain companies- and I’m not even talking about just the C-suite. My fiance, a mid level manager, travels frequently for work (think 2-4 weeks out of the month) and I join him 4-5 times a year when he is someplace new or interesting. We often will extend stays at his business hotel 2-5 days after his work trip has wrapped and his boss signs off on these extra expense always without fail. As someone coming from the non-profit world I don’t understand it at all but I’m also not complaining.

    3. Government Worker*

      I assumed this was about the rewards program account. Frequent business travelers are super into the points they get at certain big chains, just like airline frequent flier miles.

      1. Marillenbaum*

        That’s very true. I used to do a fair amount of work travel, and I was vigilant about only staying in places where I got points.

      2. Falling Diphthong*

        I assumed rewards program. And chuckled at the reasoning “On the one hand I might have to explain where all these local midday stays came from, but the POINTS!” Of all the basic desires to derail a grand coverup of anything…

    4. Old Admin*

      IIRC this is already happening? Oh boy, what a conflict of loyalties…
      …the OP might be caught betweena rock and a hard place now.

  15. Gandalf the Nude*

    Hahahaha, once, after the GM was fired, my boss took control of his email while folks were still being notified. We were chatting one day, and she was like, “He has a lot of personal subscriptions on his work email. I don’t even recognize half of it. Like, what’s RedTube?”

    And that was the day I saved my boss from googling a porn site (and then helped her unsubscribe from the other dozen).

    1. The Not Mad But Occasionally Irritable Scientist*

      Gandalf the Nude: not the hero Gotham deserves, but the hero Gotham needed right then.

    2. Zip Silver*

      I know of a guy in my company who did something similar, although he was promoted to a VP position. Well this moron didn’t clean out his work computer before making the move, and his replacement found a file full of nudes of two of his direct reports, and the boss and employees engaged in various activities. Naturally, he lost his VP job.

      I mean, come on. It doesn’t take much to delete that before leaving your computer in somebody else’s hands.

    3. Liane*

      I think you win the internet, or at least AAM, today.

      And Not Mad… said it better than me.

    4. Elle*

      We had an outside sales person who was using his company cell phone to text/set up escort appointments (he’s since been let go). I hear it made for some interesting reading.

    6. Case of the Mondays*

      I’m so glad I have a law enforcement background because anytime I have to have knowledge of something that I’d rather not admit I know about, I can claim I know because of my old job. Otherwise it gets awkward.

      1. Gandalf the Nude*

        Oh, I relish the shock value. Apparently the young-faced white woman isn’t expected to be the one to answer “Oh, Sunshine Daydreams! What a sweet name!” with “It’s a head shop.”

    7. Zombii*

      One of the managers where my mom works asked during a meeting if anyone would be interested in an employee incentive that had a 3-month subscription to RedTube for the prize. Punchline: The manager was actually talking about YouTube Red.

  16. NW Mossy*

    For a certain sort of person (which is arguably a significant Venn-diagram-overlap with “people who cheat”), the frisson that emerges from trailing breadcrumbs that someone else could follow is part of the allure. When we think we’re being so very clever in keeping a secret, there’s often a part of us that wants someone else to see and appreciate that cleverness.

    1. Cambridge Comma*

      I would suspect that he was satisfied with his own cleverness in making it sound like a business mail and wouldn’t have considered that (a) OP can see his sent mails as well as the incoming ones and (b) she would search for them and find relevant information on-line.

    2. Manders*

      I think this is more likely to be an older dude who’s clueless about technology than a deliberate attempt to make the OP uncomfortable or aware of what’s happening. Many people don’t realize that it’s possible to google an email address.

      1. Princess Consuela Banana Hammock*

        Yeah. Frankly, he sounds more dumb/clueless than secretly trying to creep out OP.

  18. Helen*

    Depending on his role in the company and/or if he at all has a public life, I might be looking for another job. I assume that prostitution is illegal where you are, and if it were me, I wouldn’t want to be associated with these kinds of goings-ons if they came to light in a scandalous way that could have an impact on YOUR reputation. Plus, if he were found out and got immediately let go (I think using company email accounts to hire escorts is for sure grounds for termination), that could mean your job is in jeopardy as well.

    It’s not an emergency, and I certainly wouldn’t bring it up with him, but I’d keep my eye open for an opportunity to leave just because I think it could mean your job is less secure than it might otherwise be.

    Also, for now, stop researching emails that could be escort services. The less you know about it, the better.

    1. Princess Consuela Banana Hammock*

      How could this possibly reflect on OP’s reputation? Aside from the CYA aspects of not googling this stuff so OP has plausible deniability, I don’t see how Boss’s behavior—if it comes to light—reflects on OP.

      1. That Would Be a Good Band Name*

        I’d hate to have to answer whether or not I knew about something like this if directly asked, especially if it turns out he’s using the company credit card inappropriately.

      2. MegaMoose, Esq*

        I suppose the extent to which this could be future scandal material could depend on the size and conservative-ness of the community, but I generally agree that in most situations, this is unlikely to blow back on the OP or even be much of a scandal. She’s not making (or attending!) the appointments, she just knows about them, and ideally, no one knows that she knows. The boss being fired over this and her losing her job as a result seems like a real possibility, however.

      3. OhNo*

        I can see how some people might jump to conclusions (of the “it was happening during work hours/from work email/using work accounts, so the EA must have been in on it and helping cover it up” sort), but without evidence those kind of aspersions on the OP’s character aren’t likely to stick.

        That said, it’s still safer to find a new job before it comes to light – because it will come to light eventually, and it’s always going to be better to be out of the blast zone so none of the crap gets on you.

      4. Helen*

        It shouldn’t, but that doesn’t mean it won’t.

        If it comes to light that boss was using company email (or using the hotel account to meet the escorts), by association, some may assume OP knew and may question whether or not OP condoned it.

        It shouldn’t be that way, of course, but guilty by association is a thing and I wouldn’t want to have to answer questions about it if I were OP.

        1. Anna*

          I think “condoned it” is a weird choice of words. It’s not like she gets to have a say on his morality or that if he were using his company credit card to book the hotel rooms, she in any way is in a position to give him permission to do it. I don’t dispute the OP should be looking elsewhere for a job; I just don’t think hand-wringing for her reputation is necessary or helpful.

          1. Gadfly*

            But, like the wife, the secretary or the assistant often gets a lot of the blame/considered to be enablers for this sort of thing.

  19. Shadow*

    I think the op should have stopped digging once she realized what was going on. why does she continue to open those emails? Seems to me she wants to teach him a lesson

    1. Princess Carolyn*

      I think curiosity would be a perfectly reasonable explanation, in addition to all the points people have made about executive assistants googling all kinds of info to make sure things are accurate.

    2. Jessie the First (or second)*

      Upthread there are people commenting who are EAs, and they talk about how they google everything – they need to, because they have to manage the calendar and also anticipate their boss’s needs, which means they need to know details. Seems to me that LW is going to need to continue googling when she finds appointments and unknown emails to and from Boss, because some of them are actually going to be work-related and she won’t know which ones are until she googles them.

    3. Bostonian*

      Curiosity/confirmation

      As someone who recently had a similar experience while googling a candidate, it probably went something like this:

      Oh, what’s this?
      Is that what I think it is…?
      Is this a mistake/accident/or has this happened more than once?

      I’m sure it’s very easy to be judg-y about it from the outside, but you never know until you’re actually in that situation. I mean, this was someone she knew and had a good working relationship with for years, of course she’d want to confirm what was happening and not just have the question of is he/isn’t he nagging her for the rest of her working time there.

    4. Temperance*

      Some assistants are expected to be really on the ball with knowing who their boss is contacting, who their boss has an appointment with, etc. In a past life, I still remember my boss saying that he wanted me to schedule a meeting with Joe at Company X, and I dug through his email to find Joe at Company X.

  20. Katie the Fed*

    Nothing good comes of saying something, OP. Just enjoy knowing this salacious secret :)

    If his wife starts asking you about his whereabouts, you have a different problem, but for now just stay quiet.

    BTW Alison, I can’t tell you how much joy this headline brought to my Monday. If I was a dog, I’d have been wagging my tail furiously.

    1. AnotherAlison*

      Wife: “Hi OP, I’m trying to reach YourBoss. . .is he available?”
      OP: “Hmmm. . .He is in the office today, let me check his calendar to see where he ran off to. . .Looks like he’s at the Hilton.” (Oops!)

      If the wife knows what he’s doing and that’s how things work for them, fine, but otherwise, I am not above dropping breadcrumbs for her to start putting the picture together.

        1. fposte*

          And in general I think you either tell or don’t tell. I understand the impulse, but dropping breadcrumbs is a bit of a power game.

        2. AnotherAlison*

          Maybe. I guess it depends how close the OP is to closing in on a new job. I have never had to deal with it in a professional situation, just friends and family.

          I do have an EA friend here who did have to deal with a cheating boss, though. The wife found out on her own because the boss kept staying with his “mom” when he was traveling to the HQ office. I guess that was weird enough that she dug into it and found he was staying with GF. Then the EA had to book boss & his wife on all future business trips for a while, at the wife’s insistence (and boss’s agreement, of course).

        3. hbc*

          I would do whatever I would do if I had no idea he was making these meetings. If you would tell his wife that he’s in a board meeting or at X customer site based on what his calendar says, then you tell him that he’s got a meeting at the Hilton. If you would normally just say “he’s not in the office,” say that.

          Maybe he’d fire OP for outing him, but unless and until he tries to get her to cover for him, he really doesn’t have anything to blame her for if she treats his supposedly innocent meetings as actually innocent.

      2. Michel*

        Are you that convinced your moral values are perfect that you feel the need to hurt other people just to justify them?

        1. AnotherAlison*

          Obviously that was what I was saying. Thank you for recognizing my perfect moral superiority.

            1. Falling Diphthong*

              An honest answer to an honest question is a weird definition of ‘vindictive.’

              If you want to have an affair, it’s on you to cover it up. You don’t get to draft your coworkers, children, neighbors, friends, and whoever else into a grand scheme where you try to assert that “lie to protect me–and lie convincingly” will become their guiding dogma.

              1. fposte*

                It can be, yes. There’s nothing special about the truth that insulates it from meanness.

                1. Tea*

                  I suppose that’s true. But barring some really pressing need, I suppose I much prefer the vindictive truth over being forced to lie to cover up another’s hypocrisy.

                2. fposte*

                  What’s being talked about isn’t being forced to lie, though; it’s deliberately including enough information to raise questions without telling them what you want them to know. If somebody wants to do that, just take ownership and tell the person, not leave them tormented.

                3. Kathleen Adams*

                  I agree with fposte – I don’t see any “forcing” going on here. If the boss said “Lie to my wife or you’re fired,” that’s being forced. But the OP outed the boss on her own, and she’s done the investigating on her own, and any responsibility she chooses to take is – so far, at least – on her own.

                  She needs to just live her life and, so long as what the boss does doesn’t affect the job, let him live his.

                  And yes, telling the truth can indeed be vindictive. I’m not saying it necessarily is here, but someone can be all kinds off awful while telling the truth.

                4. Observer*

                  The idea here is not to lie. But “dropping breadcrumbs” is a whole other issue.

                  To tell the wife or not is a question that bears some discussion. But let’s not pretend that “not telling” is the same a lieing.

                5. Zipped*

                  African proverb: All truth is good, but not all truth is good to say.

                  See also: if you don’t have anything nice to say, keep your mouth shut.

                6. AD*

                  Considering the OP came across this “truth” by essentially snooping into the boss’s emails and doing some googling, no one “forced” her to obtain this knowledge.

                7. MoodyMoody*

                  To Zipped (because I can’t nest any further):
                  “A truth that’s told with bad intent
                  Beats all the lies you can invent.”
                  — William Blake

      3. Katie the Fed*

        Nooooooo don’t do that!

        I just mean that right now his secret is none of your business. At the point that someone makes it your business, you deal with that.

        1. AnotherAlison*

          IDK, if the OP was unaware of this through her extensive googling and the Hilton reservation shows up on the boss’s calendar, wouldn’t the OP assume it’s a legit business meeting scheduled there? Telling the wife he’s at the Hilton is not implicating anyone one way or the other. If she’s a suspicious person, maybe she asks her husband about it. Otherwise, she doesn’t think anything of it.

          This is a fairly unlikely scenario, IMO, that the wife would call and ask the just-right question that would lead you into this. Would I really do this? I really would not ever be in this situation because I’m not anyone’s EA or aware of any coworkers’ activities like this right now.

          1. fposte*

            But you’re not talking about saying it because they wrongly assume it’s okay; you’re talking about deliberately hinting to a spouse based on knowledge. That’s a fun game for the hinter but it’s destructive for everybody else. If the OP wants to tell the wife, she should tell the wife, not dangle stuff at her.

      4. LQ*

        Ooof I accidentally did this. He was at a conference. When he got back he was furious. That was sort of the part when it all fell apart. And it would have been exactly what I said to anyone else. “He’s out of town at a conference, you can email him but he might not get back to you until next week.” Why? Because I didn’t even know it was his wife calling. (She was perfectly polite to me and I didn’t even realized I’d talked to her until Boss got back and yelled at me about it and told me to never answer the phone from her again.)

        1. Observer*

          That’s different. And, your boss was both a jerk and a flaming idiot. That’s not on you in any way, shape or form, for better or worse.

  21. Zip Silver*

    I know a couple of guys who are of the opinion that paying for it doesn’t count as cheating, for what it’s worth.

    Disregarding that he’s organizing this through his company email, it’s incredibly stupid to be attaching your hotel rewards account to these daytime romps, though. I hope he’s at least not using a credit card for it, otherwise he’s begging to get caught.

    1. Countess Boochie Flagrante*

      Yeah, I cosign this entire comment. I’ve known people like that too (and for the most part was not happy to know them).

      In my old job working credit card disputes, I got to see SO many people get their cheating/strip club trips/etc get busted because they paid out of a joint account or similar. Come on, people!

      1. J.B.*

        ?!?!?!?! To your second paragraph.

        I am now going to tag anyone who says anything about personal morality in my head as “probably doing things I don’t want to know about”. Because as a certified totally boring person I would never ever think to bring such things up.

        1. Countess Boochie Flagrante*

          It sure was a thing. My “favorite” was the case I got where the charge appeared as “DDP” for tipping vouchers at a PA strip club, and the guy told his wife that it was for a “Disney dining plan” and he was taking the family to Disneyworld as a surprise.

          The creativity of dirtbags is astounding.

    2. Falling Diphthong*

      I think that’s my favorite detail. That in theory one might need to explain to work or spouse where that surge of points came from, but… the points!!!! All the points! That’s a potential room upgrade in Wenoshka. You can’t just leave those lying on the ground and not take them…

  22. The IT Manager*

    I do so hate hypocrites. If you’re going to do something questionable, immoral, terrible, just own it. Don’t deny it and pretend otherwise. If you’re denying it or hiding it, you know it’s wrong. I think you might not think much of your boss’s hypocrisy either given the content of your letter.

    That said, LW, Alison’s advice is spot on. You had to search a good bit to figure out what’s going on. And now that you know, you keep searching the email addresses. Just stop. Try to forget, but definitely don’t bring it up. Given his bragging about being exactly what he’s not, your boss will not be pleased to know his cover has been blown and will very likely take it out on you.

  23. Anon for This*

    I had something similar happen years ago, when I was an intern. When my boss was out of the office, I was tasked with managing his email. I opened an email from one of our board members, assuming it was about work, only to find… something more graphic. Turns out they were having an affair.

    (This story had a sad/complicated coda. This was a gay rights organization; my boss (a man) identified as gay, and the board member (a woman) identified as a lesbian. It was very difficult for them when the relationship became public, as they had to grapple with their identities and other colleagues’/supporters’/members’ biphobia.)

    1. Marillenbaum*

      Ooh, ouch! That is a really unfortunate situation–especially for you, as an intern. And there’s nothing like a bit of biphobia to add zest to the day . It’s a rotten thing to deal with.

    2. Manders*

      Oof, that’s rough. Did your boss not realize that someone was going to be monitoring his email, or did he just not realize that the board member would be sending things like that to his work account?

      On a more general note, I’m curious: do commenters think the issue of inappropriate stuff in work email accounts will get more or less prevalent as digital natives age up into this kind of leadership position? On one hand, we’re more used to the idea that creating a new gmail account is easy–but on the other hand, so much communication routes through our phones now that making a mistake and using the wrong account/texting the wrong person/making autofill accidents seems REALLY easy.

      1. Countess Boochie Flagrante*

        Honestly, I would say I think it will continue to happen because communications technology will continue to evolve and so there will always be people using something that is new to them and with functions they don’t fully understand.

      2. Falling Diphthong*

        Everybody who successfully covers up their affair–new email, burner phone, not leaving Chat open on the home computer–fails to generate a letter to an advice columnist.

      3. Princess Carolyn*

        I’m actually wondering how digital natives will affect the concept of EAs (and others) monitoring email for their bosses. I get that many executives are capable of using email and simply don’t have time, but… I have to guess that’s partly because they’re not as quick as a digital native would be. I’m sure it would depend on the type of work and the company itself, but I predict fewer people will be sharing their professional email accounts.

      4. Bryce*

        I think it’ll continue because, even if you’re savvy, you only need to forget once to screw up.

  24. Jessesgirl72*

    OP, you need to stop looking for these emails.

    I can see wondering about the first email (although, you knew it wasn’t the one you were looking for….) and maybe googling to see who it was from, but after that?

    Now you know your boss is a flawed human, like us all. He is stupid to use his work email (or maybe just his Outlook?) but that is on him. If he gets caught, he gets caught. Since he’s not subjecting you to all this, but you have to go looking for it, it’s definitely a case of you worry about your job and let him worry about his.

    1. J.B.*

      One other possibility is if something originated from his phone he might not even realize what account it came from.

  26. Anon for This*

    I should have said:

    1) I didn’t say anything, to my boss or anyone. I just pretended it never happened. He must have known that I knew, since he could easily see that the messages had been sent while I was managing his inbox, but we never discussed it.

    2) The similarity here is only in the awkwardness of knowing something you shouldn’t about your boss’ sex life. The relationship my boss had was very different from the OP’s boss hiring an escort.

  27. Observer*

    I’m with Alison. I also agree that you should stop looking.

    The only concern I have is whether he is paying or the company. If it’s the company, that’s a bit icky, but unless YOU are setting up the bookings, it’s really not your business. It *does* however, tell you something about this guy’s integrity. (So does cheating on his wife, but you don’t know for sure that his wife wouldn’t approve.)

  28. Countess Boochie Flagrante*

    People who talk about not cheating as being a sign of great dedication or a great sacrifice on their part are generally people who are either cheating or who want to cheat but haven’t had the opportunity, in my experience. If you don’t want to in the first place, how is not doing so any kind of a big deal?

    2. MegaMoose, Esq*

      Yeah, assuming this didn’t somehow come up naturally in conversation (which still seems odd at work) this is definitely along the lines of “I wasn’t worried you were going to eat my skin until you promised not to.” So many things go without saying!

      1. Countess Boochie Flagrante*

        “I wasn’t worried you were going to eat my skin until you promised not to” — I love it!

    3. OhNo*

      Exactly. I think part of the problem that people who do talk big morals while doing exactly what they rail against (like the OP’s boss) have is that they don’t realize that the rest of the world really doesn’t think about it as much as they do.

      People who proclaim loudly and often that they don’t cheat are already putting waaaaay more thought into the possibility than truly content monogamous people do.

    4. Temperance*

      I will never, ever forget when Booth’s former boss encouraged him to cheat on me – as in, his boss offered to “introduce” him to a prostitute when Booth was visiting his location, because apparently David frequented escort services when he traveled, and assumed that all men do. (Booth declined.) This guy was fired after somehow managing to expense something like $20k in stripper and prostitute charges over a few years.

      1. neverjaunty*

        As one wise male colleague once told me, nobody *dabbles* in hookers. Guys who hire escorts behind their SO’s back do so on the regular and don’t see why other men shouldn’t do the same.

  29. animaniactoo*

    OP, repeat after me: Not my circus, not my monkeys.

    If your boss has managed to live through the age of Elliot Spitzer and Anthony Weiner and is still running this through his work e-mail, hey – that takes some serious obliviousness.

    Now note – he’s being somewhat cautious. I mean, you did actually have to check and track down the e-mail addresses themselves, there was nothing in the e-mails themselves that was clear and descriptive. But still. He’s an adult. He’s got multiple places to get the message from and he’s choosing not to believe “yeah, you too buddy”. Not your circus, not your monkeys.

    Possible positive reframing – you note that he’s doing this “on company time”. I would see it more as he’s taking personal time during the day (at his level, I’m going to assume that he ends up handling company business in his personal time, so this is a reasonable trade). Yes, it would be better if he called it personal time, but you might understand why he wouldn’t want to do that as it would lead to questions about why he was taking personal time during the day, etc. It’s a little shaky in concept, but if it helps you feel better, go with it.

  30. Katie*

    I guess I guy that is faithful doesn’t even think to announce it, it’s just normal, nothing to talk about. OP’s boss is almost expecting a medal for not cheating despite the fact he’s actually cheating…

  31. Michel*

    I can’t believe how many people here think it is ok to keep googling someone’s private emails, he obviously think you can’t see them, and he does not now that someone is putting his send mail box through google.
    The correct action if you really had a valid reason for checking the first email, would have been to ignore any others. But OP keep searching for prostitution emails just to confirm her outrage.

    Also ask yourself why you are doing this, for some set of values that YOU think are correct? You have every right to think about this kind of behaviour what you want, but you have no business with someone else his private life, nor are your values the be all end all, different opinions, values and POV do exit.

    You also don’t have all the info about his family life, not everything is black and white, there can be millions of different reasons/agreements/history/whatever going on.
    The only thing you know is he meets escorts, this has no impact or ramifications for your own life or work so why do you think you need to be the one “fixing” this “problem”?

    Read these letter pages, a lot of people have horrible workplaces, do you want to ruin yours that is perfectly fine for some moral high ground principle thing?

    1. Countess Boochie Flagrante*

      As other people have pointed out upthread, these are work emails and it’s very routine for an EA to google ambiguous appointment/meeting info so that they can keep their boss’s calendar running properly.

      1. Michel*

        But there is no need to keep doing that, 1st was an accident maybe, but why keep looking?

        1. Jessie the First (or second)*

          Because she needs to regularly check his emails, that is part of her job. That’s what EAs do.

          1. Michel*

            She does not need to regularly look on google to confirm escorts, it is clear what these messages are, plus she is getting them from a send mail box that he does not now is shared.

            1. Temperance*

              The thing is, though, she does have to keep reading his emails, and it could put her job in jeopardy if she misses an email about scheduling etc. because she’s trying to avoid anything that might include an appointment with a hooker.

              1. Falling Diphthong*

                This. I can see it now.

                Manager and Grandboss: “You dropped the ball on reminding Manager of the appointment with Boopsie Bopper!!!!”
                EA: “But I figured it was one of his escorts!”
                Manager: “They do IT security!”

                1. The Not Mad But Occasionally Irritable Scientist*

                  I chuckled a bit, then the last line hit me and I died.

            2. Jessie the First (or second)*

              If it is clear what the messages are, then she should stop googling them, yes.

              But there is zero in the letter that suggests the emails are at all obvious – sex workers are people with email addresses that run the gamut of ordinary, like anyone else; they do not all have email addresses of “ImAHooker@YeOldeBrothel.com.” And an email that asks if someone “still has time to meet today,” which is the actual example from the letter, could easily be an actual work thing. I have sent emails with that wording, and generally, you know, I’m not talking about paid sex when I do.

              I really think you are projecting onto this letter an angry judgment that is. not. there. from the LW.

      2. Government Worker*

        Yes, this. I spent time as an EA before grad school, and the relationship that I had with my bosses was totally different than it is now, when I’m in a project-focused role. When you’re an EA with access to your boss’ email and calendar, you’re often *expected* to keep tabs on everything to make sure the calendar is up to date. It’s not typical to read all sent mail routinely, but it is normal to go looking for specific email addresses, meeting info, files, etc. in the sent mail. I googled lots of stuff, including people I didn’t know, to see whether I needed to ask my boss about it and so that I could prepare materials, schedule around it, etc.

        I worked for three different bosses in an EA role, and I knew about when they jealously guarded their morning gym time and when I could schedule breakfast meetings, when one boss was attending AA meetings (he was pretty open about it), where doctor’s appointments were so I could allow enough time for travel from the meeting immediately prior, etc. One boss was straightforward that liked to stay in the gayborhoods of big cities when he traveled (he’s gay). I have no idea if he was in an open relationship, cheating, went out clubbing all night, just enjoyed the atmosphere, or what. Not my business except for booking an appropriate hotel, though I admit I was curious. Good EAs are both very nosy and totally discreet, because both stumbling on and being told personal information is part of doing the job well.

        Now, in a non-assistant role, I can imagine it being appropriate to know any of this stuff about my boss.

      3. neverjaunty*

        While this is true, and the OP looking at his work emails is not in and of itself terrible, OP makes it clear from her letter than this is curiosity and not necessity forcing her to look up these escorts.

    2. Jessie the First (or second)*

      Ditto what countess said – EAs have chimed in here to say that actually, searching through emails and googling is normal for an EA (and BTW, the emails are not private; they are work account emails).,

      But also – the LW herself notes that maybe the wife knows, maybe this is all just part of their arrangement (and hey, she explicitly says “who am I to judge?”) . The tone of her letter is not ZOMG GUYZ GUESS WHAT!! But you’re responding here as if is saying exactly that. Whatever he does in his private life is none of anyone else’s business, but if he’s booking rooms in the middle of the work day, his work would most likely care. I agree with Alison here that her best course is to not say *anything* and just keep doing her job. But you really are arguing against an attitude that I do not see in the LW’s letter.

      1. Michel*

        but she is judging, the whole point of the letter is that he is doing something despicable that maybe she needs to fix.

        That’s why she keep spying on his private life.

        It doesn’t matter if the wife kows or not, it is not here buisiness to judge him nor fix him.

        1. MegaMoose, Esq*

          Nah, I agree with JtF(oS) – I think the tone is less “what a monster!” and more “do I have a moral obligation to warn my boss about how easily I found this?” Which is a perfectly reasonable question to which I think the answer is “no.”

        2. Temperance*

          I think it’s fine to privately judge hypocrites, FWIW, especially those who loudly boast about how morally upright they are.

          You are right that it’s not her business what happens in his marriage, but she can’t unsee these emails, nor can she reasonably avoid them in the future if she wants to do her job well.

          1. fposte*

            I think it’s fine to privately judge everybody, actually. But then I’m pro hypocrisy when it comes to getting along with people you privately don’t like much.

            1. Falling Diphthong*

              This. “Hypocrisy is okay at work” is a bit of a theme over the past week.

    3. MegaMoose, Esq*

      Although I agree that the OP should probably back off on the googling, these are in no way private emails. I mean, my job is literally going through people’s work emails all day looking for stuff responsive to lawsuits – you’ve got no right to privacy in a work account.

      1. Falling Diphthong*

        But what if she fails to remind him of a midday appointment with Truly Scrumptious, and it turns out to be a catering company?

        1. MegaMoose, Esq*

          Then maybe Truly Scrumptious should think about investing in a custom domain name and email signature? I’m having a hard time imagining this really being an issue. But hey, if she wants to keep with the googling, that’s fine too – I don’t feel especially strongly about that part. One of the only things I actually like about my job is being paid to be nosy.

          1. Falling Diphthong*

            My idea was that “Don’t google anything from his work emails or work calendar that might possibly be an escort–but do google anything that might possibly be work related so you’re on top of work” is an unrealistic standard.

            1. MegaMoose, Esq*

              The point of my comment was simply that these aren’t private emails, so I think you might have read too much into my tossed off “probably back off on the googling.” I totally agree with your standard, but I think you can follow that standard without tracking down the phone number of any unidentified email in the sent folder without some other reason to do so. Do what you need to do to do your job, and recognize when you’ve moved past doing your job into snooping. And I’m on record in this thread as being pro-snooping, but I’m also pro- keeping it to yourself.

      2. AMPG*

        Yes – there are SO MANY stories out there of people who got themselves in serious trouble thinking their work email accounts were private. They just aren’t.

      3. Jessie the First (or second)*

        “my job is literally going through people’s work emails all day looking for stuff responsive to lawsuits ”

        Oh gosh, yes times a million. In my first few years of practice, I read so. many. emails. from people who clearly thought of their work email as their own private email – so I read lots of sex-themed emails to wives and husbands and affair partners, as I combed through the entire email trove of companies during lawsuits. Dozens and dozens of people read through every email, really. One particular lawsuit, one particular company, one particular VP sent very, very graphic emails regularly to his, uh, special friend. Made my eyeballs burn and I remember it years later. Ugh.

        Nothing about what happens in a work email is private. So I don’t have any patience for an argument about how DARE she snoop. If you want privacy, use gmail.

      4. neverjaunty*

        It doesn’t matter whether these are “private emails” – if I emailed my physician from work, it’d be freaking creepy and rude for my assistant to say “Oh hey, I see that you emailed a doctor and so I looked up their specialty, and printed out the relevant pages from our insurance benefits and left them on our chair”. Even though there’s nothing whatsoever weird or gross about seeing a doctor. If it’s not malfeasance, maybe don’t be nosy?

    4. Tea*

      Well, this is literally her job. Like, all of it, down to the tracking individual emails. I think you’re letting your own outrage that a cheater might face some kind of moral judgement (that the OP has not expressed) color your response here.

      I am not an EA, but I work in some EA-like capacities to my boss. My boss wants me to dig something up from the depths of his email? I google, root around, and find all the people involved, confirm the dates, times, and locations. Sometimes, people try to sneak past the gatekeepers and book what are basically sales meetings with him under the guise of networking– I look those up too, confirm that the people are sales people and not who they claim to be, and manage his calendar accordingly. Fraudulent charges? Guess who’s calling Citibank and identifying each strangely named charge to its appropriate source? Now, I only do this now and then, but if my boss had something to hide? It would be easy peasy for me to uncover it, even just by accident.

    5. Isabelle*

      There is a much bigger problem than morality here.
      What if someone finds out the boss is meeting escorts on company time in hotel rooms presumably paid for by the company? He is defrauding the company.
      OP risks losing her job if that happens, even if she didn’t do anything wrong.

      1. Jessie the First (or second)*

        I don’t think there is anything to suggest that the company is paying for hotel rooms for his visits with escorts. LW just mentions that she has access to his hotel account – that could be his personal rewards balance, or that she has his room details and can see online (you can book online, so he maybe just gave her his login – but that doesn’t mean the company paid it). If the company were actually paying for his hotel room trysts, that would be a problem – and I feel like the LW would have mentioned that. Not buried it at the end of a long letter where her main concern is emails.

        1. MegaMoose, Esq*

          Plus, it’s pretty likely he’s salaried exempt, which means the concept of “company time” doesn’t apply.

          1. Anna*

            You very succinctly described what has been bothering me about a lot of the comments people have been leaving.

  32. The Smile on a Dog*

    I think just because you have access to his email doesn’t mean you should be looking for/at things that aren’t within the scope of the job at hand.

    Other than that I agree with Alison: it’s not your job to save him from himself.

    1. Yorick*

      I agree. She said she went to his Sent folder looking for a specific email, and then seems to have just been curious when she saw a message to a gmail account. I think it seems a little less like a work-related google search than other commenters believe.

      1. FlibertyG*

        TBH I kind of thought the same thing. Whoa there, Nancy Drew. I don’t think you need to keep googling all these email addresses at this point.

  33. Retail HR Guy*

    When OP says she has access to his hotel account and can see that he’s booked rooms, could that mean that the rooms are being paid for by the company? If so, then I think that shouldn’t be ignored because it’s gone from being his personal business to (light) embezzlement and the exec’s boss should know about it.

    But it might just mean that OP can see from his “Hilton Rewards Club” account or whatever that he has indeed purchased rooms on his own dime. If that’s the case, I agree with everyone else here to just ignore it.

    1. Temperance*

      FWIW, at least at my firm, it seems like many of us tend to use the same chain of hotels and our personal Amtrak accounts and then just expense them. That way, we keep the Amtrak or hotel points for personal use, and get reimbursed for the work expenses and pay out of pocket for anything personal.

    2. Jessesgirl72*

      Since she also “coordinates travel plans with his wife” it may even be a personal rewards club account, and not the same one he uses for work.

  34. Spek*

    I hope your “other reasons” for leaving are more substantial than this. Personally, I would cherish a boss who was a “good guy to work for” in a challenging position who’s only fault was that he was (possibly) unfaithful in his marriage, and a little careless in covering his tracks. A good boss is a thing to be treasured and makes the percentage of your life spent at work so much easier…

    1. LQ*

      This may be personal but I would leave in a heartbeat. I worked for a boss who did this and brought down the entire organization and it was devastating. Once you do one unethical thing (that you personally and LOUDLY proclaim to be unethical) there is nothing stopping you from doing other unethical things. Like putting those hotel rooms on company cards. And next thing you know you’re sitting on the floor surrounded by boxes and boxes of paperwork from your former boss who left you with grant application STUCK to condoms STUCK to printouts from adult sites.

      Sure it might seem like “good boss” behavior in other ways. But if you say X is unethical and then do X? What stops you from doing Y thing that you say is unethical. Surely not your ethics.

      2. Anna*

        That is patently not true. Plenty of people do unethical things without sliding into complete loss of ethics. There’s no unethical gateway act and it’s all downhill from there. The person who cheats on his wife is not MORE likely to steal from the company or lie about their timecard.

        1. Jake*

          That’s so interesting that you say that because my gut reaction was to strongly disagree with you, but then I brought it to the logical conclusion of, “is the guy who speeds 3 mph over the limit more likely to steal, cheat and murder?”

          My guess would be that yes he is more likely, but only marginally so. Plus, more likely does not equal guaranteed.

          Overall, I think there is some value to LQ’s point, however, a chance at falling down the slippery slope probably isn’t enough for me to jump ship for just what I’ve seen here.

          1. Anna*

            I couldn’t disagree more. I would wager that more people on a daily basis speed and the vast majority of them would not consider committing a murder, cheating, or stealng when faced with that opportunity. I think if the people who do end up going there would have gone there on their own and they didn’t have to start with cheating on a spouse or speeding. Everyone’s line is different, but I think the majority of humanity don’t start at point A, realize they got away with A and move on to B, get away with B and move on to C.

          2. Mike C.*

            The problem is that you’re looking at these crimes in terms of severity alone, when people commit them for very different reasons. You can’t really draw these sorts of conclusions in a meaningful or predictive manner.

            1. Sarah G*

              Wait, 3 mph over the limit is speeding? I couldn’t even keep up with the flow of expressway traffic without going 5 over. Technically, I know you *could* be ticketed for 3 miles over, but given the inaccuracy of speedometers…
              I don’t call it speeding unless it’s more than 5 over the limit. But I’ve lived in big cities most of my life, so that could make a difference. It would be interesting to take a poll.

          1. Mike C.*

            Just out of curiosity, do you write a lot of your articles far in advance in general?

            1. Ask a Manager* Post author

              I write everything for the week on Mondays (except for the short-answer posts, which I write throughout the week). So I haven’t written the answer to the Very Interesting letter yet, but it’s sitting in my queue for next week. (I didn’t use it this week because I have something else about an affair already done for NYMag tomorrow and didn’t want too many affair posts in one week.)

    2. Manders*

      I personally wouldn’t leave for this reason alone if the workplace was otherwise great. I know some folks who would, though, and that’s a totally legitimate choice to make.

      Something I had to adjust to when I became an adult was understanding that people in a position of authority over me aren’t necessarily wiser or more moral. When you’re a kid, you look to adults for moral guidance; when you grow up, sometimes you have to tell yourself “I wouldn’t have made that choice personally, but it doesn’t impact my ability to work with Bob.” And once you can make that distinction, it’s easier to tell when Bob *is* doing something that’s not just personally distasteful but an issue that the company needs to be aware of.

      1. LQ*

        I’d feel much more likely this way if the boss wasn’t loudly proclaiming the immorality of this specific action. If he was quiet about it. Or when it came up he was more “humans are flawed and do the best they can but sometimes fail”, yes…they are and we do. But to me the hard line makes me want to say run away! Often people who are very hard line will consider all steps over the line equal in wrongness. (Looking at a woman with lust and paying for an entire second family are exactly the same thing for example.) And that makes me concerned about other things that he’d be willing to do. Is he also willing to gut the company and leave us bankrupt? Because that’s exactly the same amount of bad as taking a long lunch. Stealing is stealing if you think that hard line means everything on the other side is irredeemably bad then once you’ve stepped over it there is no reason to go…oh…maybe if I stop now it can be ok.

    3. Student*

      Good bosses don’t steal from their company. At minimum, the email makes it clear he’s spending work time on this. It sounds possible he’s spending work money on the hotel, too.

      1. Yorick*

        If he’s senior and has a flexible schedule, it’s likely that this shouldn’t be viewed as “work time.” Doing something personal in the middle of the day isn’t stealing from the company when you work 60 hours a week.

        1. MegaMoose, Esq*

          You know, I hadn’t thought about it that way, but you’re totally right – assuming he’s exempt salaried (which I’m guessing is a good assumption) he can do whatever he wants during “work time” so long as he’s also doing the work he’s being paid to do. My dad used to take naps under his desk mid-afternoon back when he was a GM – if he’d been hourly, that would have been dishonest, but as he was salaried exempt, it wasn’t.

          1. Jake*

            Yeah, I think its safe to assume that a worker with an EA is exempt. It is literally not possible for him to steal time from the company, at least on his own behalf.

  35. Matilda Jefferies*

    I’m going to disagree with the majority here. If you work for a government organization, this is almost certainly something that should be reported. The higher-ups would absolutely want to know that your boss is using taxpayer-funded resources to procure escort services. There is very likely an ethics office of some sort that you could report to, and you should be protected from reprisals if you do. The alternative is that if he gets caught by someone else, there may also be questions as to how much you knew and when, and why you didn’t say anything sooner.

    It doesn’t sound to me like you do work for government, in which case you may be fine to just ignore the whole thing. But I wanted to throw it out there that Alison’s advice may not be universally applicable – government is often the exception to a whole lot of rules.

    1. MiaRose*

      True, a friend of mine worked for a city government office, where all manners of things in his department were happening. Despite his education, he was low man on the totem because of his age and newbie position. His boss watched porn on a company computer, another coworker took 2-3 hour long lunches, then came back and did internet-shopping for most of the afternoon. None of them, aside from him, had a working knowledge of IT. He basically gathered up intel on the whole lot of them (after he finished his own work), then quit, sending the intel to one of the directors. That he was able to do all his own work, fixed up some of other people’s work, and still had time to hunt up intel, was amazing.

    2. LQ*

      If you work for the government you should also know that chances are extremely good your emails are discoverable too.

  36. The Strand*

    When you’re an executive assistant, sometimes you have to arrange meetings for your boss, answer emails for your boss, send out meeting requests and messages “on behalf of Person, Boss”. You are expected to “think” for your boss, and that sometimes includes exploring strange emails to see if it’s something Boss Person half-remembered and needs right now.

    So I get how you found this in the first place, and there’s no shame in discovering it. But yeah, you should just assume that at minimum, he’s continuing to use escorts – and if you keep checking Google, you’re just going to be annoyed, and lose more and more respect for him as you confirm that it’s happening on company time, etc.

    As someone who was briefly a EA for a guy who watched porn in the office – with the door open – the best revenge is to get a new job. The goal is to get it to be a funny no-name story you tell your friends, looking back after a great career. If you have the time to Google, there’s probably something more beneficial to do with the time – like update your resume.

  37. MiaRose*

    Someone mentioned deniability above. It just occurred to me. If you are Googling the phone numbers and other related information on your own work computer, could this be traced by the company, and, then, could you get in trouble for having known about these things and not reported them? I’m really curious about this. I’m paranoid about info, and would always use my own phone or devices to Google stuff if I was at work.

    But I would consider brushing up that resume, in case things go south.

    1. Jessesgirl72*

      Unless he’s using the company credit card, so stealing, there is likely no required reporting here.

    2. Student*

      My company would consider her complicit in spending work resources on decidedly “personal” expenses and fire her immediately if it was discovered by some other path that this boss was engaging in this conduct and the OP knew but didn’t report it.

      1. Falling Diphthong*

        He doesn’t seem to be charging the expenses (escorts or hotels) to work. The time missing from work is proooooooobably no worse than if he occasionally met his wife, rather than escorts, for lunch with a hotel room. (Assuming he’s exempt and works long but flexible hours.) And many people can accumulate points through a work account for car rentals, hotels, etc, while personally paying personal expenses–it’s not *wise* to do this through any trips you wouldn’t want work to know about (like job hunting elsewhere), but it’s not stealing from the company.

        1. Anna*

          Yeah, there’s a lot of assumptions being made about how the boss books hotels and so on. It seems like if that were an issue, the OP would have included it because it would probably change Alison’s response a little (maybe not).

      2. Jessesgirl72*

        Since he already has her do personal errands for him, that is presumably paid for by the company, it’s probably safe to say the small amount of “resources” being spent- since she didn’t say he was paying for it with the company card- is in the acceptable range.

    3. nonegiven*

      Yeah, I was wondering if she cleaned up, deleted those searches from her history

  38. regularAnon*

    So the boss is definitely not in an open marriage, poly, or practicing ethical monogamy? Then stay out of it. This is going to blow up in his face.

    And I would never use work email to arrange assignations, because it would look REALLY bad. Even though my wife and I are on the same page about them, so I’m not cheating. The worst that could happen with me is that, since my “date” is an IT person in another department (we did not meet at work), things might be slightly awkward. But that’s on me. I can’t expect to take my personal life to work with me like this boss does.

    1. Falling Diphthong*

      She says she doesn’t know if he’s in an open marriage or not.

      But that gets at something fairly brought up in your second paragraph–“How much of this am I supposed to lie to his wife about?” is not a question you should be raising in the many people who can see your work email. Either be open with them that you will get some from the extramarital people you’re sleeping with–or, better, keep those people on a separate email account that doesn’t touch work.

    2. Kathleen Adams*

      Look, she just shouldn’t get involved. Even if he were in an open marriage, that doesn’t mean his wife is open to EVERYthing. It’s best not to even attempt to figure out what’s acceptable in someone else’s marriage.

      She needs to just butt out, and if it makes her uncomfortable (and it surely would make me uncomfortable), get a new job.

    3. Zombii*

      What’s ethical monogamy? Seriously question because google is useless on this one and if it’s not a typo I am super curious.

      1. silence*

        I’d guess they meant ethical non monogamy which is being open and up front about having multiple relationships

  39. Amber Rose*

    In times of trouble, we can count on Buzz Lightyear to give us the correct response: “He is a sad, strange little man, and he has my pity.” (paraphrased, obv.)

    I know it irks you, but feeling a little annoyed is not worth the trouble you’d be causing yourself by getting involved. Best to try and turn your annoyance into amusement.

  40. Holly*

    The LW hasn’t mentioned it, but is the boss booking these hotel rooms and such with the company credit card? Because *that* might be something to consider reporting.

    That said, people having affairs via work emails is actually really common as I have found out from having jobs which required review of company emails.

  41. Malibu Stacey*

    I’ve come across something like this in every admin job that I have had – the people who answer the phone and open the mail find out the stuff you wouldn’t want anyone to know.

    1. Temperance*

      Yep. I have caught men viewing porn, found really gross and weird stashes of porn, a man having intercourse in his office with a woman who was not his wife, read a pretty salacious attorney letter regarding a divorce (our client knocked up his mistress), and found weird not-porn sexual photos.

      I would just smile, nod, and move on … with the exception of the time I caught the guy en flagrante. I avoided him for a really long time after that. If you’re going to bone in your office, how about you don’t do it against the door and throw her panties in your window, k?

      1. Falling Diphthong*

        This. This is what I mean by believing themselves to be masters of subtlety whose behavior would not raise the tiniest whiff of suspicion in any observers… unless those observers are sneaky masters of betrayal and lying, who cheated to gain that information.

  42. formerly Nina*

    It would be awkward for the EA to approach the boss (because she would have to admit snooping the email and googling names.) However, if he is truly using the hotel rooms for meeting prostitutes and putting it on this office account (and work is paying for it) … that is fraud. If it comes to light down the road and anyone suspects EA knew but didn’t say anything she might be in trouble.

  43. Allison*

    Personally, I wouldn’t say anything to him. He might get angry if he knew I went poking around like that, or defensive about his actions even if I didn’t say anything judgmental. It might be old fashioned and sexist, but people with assistants generally just want their assistants to assist them, and look the other way if they see notice anything they’re not supposed to know about. I think reporting him, either to his employer or to his wife, might wreck me professionally.

    Also, if it were me, I’d probably polish up my resume and start looking at what else is out there. Not an urgent job hunt, just applying here and there when something interesting happens to catch my eye when I’m browsing job boards in the evening . . . The whole thing would make me feel squicky. I mean, good that he’s paying for it rather than trying to get his “side kicks” with me, but still . . . not something I’d wanna be close to.

  44. Blue*

    I only recently realized that once I accessed my gmail account at work, ALL of my personal gmail history could now be seen on my work computer. It sounds stupid but frankly it was astonishing. I had no idea. Check your own work computer, you might be surprised.

    1. Zombii*

      This. This is why I refused to connect my work Gmail account to my personal Gmail account (as instructed), and would only go to my personal Gmail in an incognito window at work and my work email never at home ever because I was hourly and refused to check my email off the clock (also as instructed).

  45. Pebbles*

    OP, I would be concerned about googling these email addresses for another reason that I haven’t seen pointed out yet: these searches become part of your Google history, which your IT department could certainly see and ask you about! I’m not sure what sites you are finding that lets you know these email addresses are linked to prostitutes, but if the site content is flagged in any sort of web filter, at my office that visit gets logged to IT. You would certainly out the boss’ secret if your search history was flagged!

    1. Countess Boochie Flagrante*

      Good point! When I worked in disputes, I ended up researching some sites that ended up being in the “ohhhh man IT’s going to have a field day with this” category. My response was to give my boss a proactive heads-up. Not something the OP can really do in this case, though!

  46. Mrs. Boo*

    I’m kind of surprised that no one has touched on the potential liability for the company if one of the escorts services were to try to leverage this information against her boss. Wouldn’t the CEO want to know of the potential exposure?

    1. MegaMoose, Esq*

      I don’t really think this is anything the company could possibly be liable for here – if an exempt employee wants to take a long “lunch” and do something illegal during it, that’s on the employee, not the company. There’s some possibility of bad PR, but I think that’s going to be regional and in many (most?) places no one’s going to care.

      1. TootsNYC*

        I think the point is, “is he blackmail-able?”
        Might he be pressured into revealing company info, helping someone deal drugs, or embezzeling?
        Or might he be pressured into paying out money, which would greatly increase the likelihood that he’d do something illegal or unethical to GET that money (like ask for kickbacks from vendors)?

        1. MegaMoose, Esq*

          Ehhhhh, I guess that’s a possibility, but I don’t see that it’s an especially likely one. Lots of people are theoretically blackmail-able, but unless his job is specifically linked to his moral character, or there’s something else going on the OP didn’t mention, it just doesn’t seem worth getting worked up over. I’m guessing most people in the sex industry would rather have a repeat customer than blackmail someone.

  47. Student*

    I would bring this to the attention of his boss because he is spending company money on it. It’s against the law to frequent prostitutes (at least where I live), but something many people would overlook as someone’s private business rather than report to the police. However, stealing company money to frequent prostitutes is not acceptable at all. You wouldn’t be expected to tolerate it if he was stealing company money to go watch his kid play soccer out of state, that’s something most companies would expect you to report as a major violation. Spending work time on a “meeting” with a prostitute likely costs the company even more money than the hotel does, so that’s also a serious issue of timecard fraud.

    1. Ask a Manager* Post author

      Eh, I think that’s a stretch. He’s presumably exempt which means that “work time” isn’t the same as it is for someone who’s non-exempt. It’s the same way that it’s not stealing for exempt workers to take a long lunch or go to the doctor or head out early sometimes.

    2. Temperance*

      Taking the morality of him paying for prostitutes with his own money aside, it’s not theft. Here’s a more dull example: I’m exempt, and I was bored this morning so I walked over to Rite Aid to buy some makeup. It’s on me to manage my workload, and if my boss considered walking to Rite Aid to buy makeup theft, I would find her ridiculous.

    3. Anna*

      You’re making loads of assumptions based on nothing. The OP doesn’t mention booking rooms with a company credit card, so I think it’s safe to say that isn’t an issue. And as has been pointed out already, an employee with EA is probably exempt so he can’t technically steal time from the company.

  48. RVA Cat*

    OP, does your the scope of your job involve things like scheduling his annual physical, and his wife’s? If so, the only thing I can think that may help your conscience a little bit would be to make sure his wife visits her OBGYN soon, just in case your boss may have given her an STI.

    1. Jessie the First (or second)*

      Wooooooaaaaaahhhhhh, that’s invasive. I can’t believe any EA’s job is to schedule pap smears and STI tests for the boss’s spouse.

  49. Troutwaxer*

    Something we don’t know is what part the wife may be playing in making the relationship either good or bad. I really feel sorry for fundies because they’re raised to be so messed up about sex that its just about inevitable that conflicts arise which people who aren’t messed up about sex could settle fairly easily. (Not that there aren’t hard problems for people who aren’t messed up about sex, but that’s another matter.)

    1. Temperance*

      … really?

      His wife is not the reason that he is purchasing sex from prostitutes. If they are BOTH uber-religious, he knows better, and he was taught similar lessons about the impropriety of sex. He was probably told at church that it’s women’s fault for tempting him, even though he knows better. His wife was probably taught, as we all were as fundies, to be modest.

      It’s actually incredibly sexist to blame his wife because he can’t keep it in his pants and because he doesn’t have the good sense to troll Craigslist with a throwaway gmail, like the rest of us. We aren’t responsible for men’s stupidity and misbehavior, even if we were raised to think that a man seeing our shoulders or knees would cause him to sin out of control and run on a sex binge.

      1. Troutwaxer*

        My point had more to do with noticing a fair bit of husband-blaming above. There are two people in every relationship and we don’t know which is the real problem here, or whether both have done their share to mess up the relationship. I’m certainly not trying to engage in misogyny; in my experience both sexes are equally horny and equally likely to seek out company from outside the marriage.

        I have certainly noticed, however, that the messed up part of fundamentalism falls more heavily upon the women than the men. This is not to blame the women, but to instead blame fundamentalism.

        For both the men and the women, living under patriarchy is no fun. :-(

        1. Anna*

          Well, to even start, you don’t have to be a “fundie” to be a Christian who doesn’t believe you should engage in sex outside of marriage. You don’t even have to be a Christian to adhere to monogamy. Secondly, whatever the nature of their relationship, unless he and his wife have an agreement about him going outside their marriage for sex, the decision to see an escort is entirely on him. His wife is absolutely not responsible for the poor decisions he is making. Nobody is “husband-blaming” unless you think holding someone responsible for their own potentially crappy behavior is blaming someone.

        2. Falling Diphthong*

          The issue isn’t who’s truly to blame by what percent if he is cheating. The issue is the EA being put into a position to wonder “Is this an open marriage, or am I supposed to be covering this up if his wife asks where he is?” and “Should I tell him this is easy to find, and IT, legal, etc might also run across it? Would he be grateful if I gave him a heads-up about using a separate gmail for his on the down-low pursuits?”

          It’s quite common for an EA to give a spouse more than “I’m afraid Mr Boss is unavailable at this time; shall I take a message?” And now she has to guess whether she’s supposed to start altering her response, which meetings she should research and which she should pretend not to see, and so on. It’s an uncomfortable position in which to put his employee.

        3. Observer*

          None of this matters in this context, though. The husband is being blamed because HE is the one sneaking around (if that’s what it is) and being an idiot in the bargain. No matter how messed up his wife may be, and no matter what the reason is, this is on him.

          If he were walking out on her, it would be fair to ask whether she precipitated it.

        4. neverjaunty*

          For pete’s sake. People are “husband-blaming” because the guy is bragging about his Moral Stance while doing exactly the opposite in his private life. It’s really not necessary to do some kind of bullshit ‘on the other hand’ by making stuff up about the wife.

        5. Temperance*

          Well, I think it’s fine to “husband blame” when the husband is the one stepping out on his wife. That being said, the issue here is more relating to the EA and her responsibility. I just had to respond to the point that the wife was somehow responsible for her husband choosing to have sex with strangers and expose her to who knows what.

        6. Temperance*

          I also find it mildly ironic that you’re criticizing the patriarchy here, when your previous comment was a pretty big example of it.

    2. Emi.*

      Wait, what? It sounds like you’re saying you have to be a “fundy” or “messed up about sex” to think cheating is wrong and fidelity is good, and assuming that he’s cheating because of a conflict they should have been able to settle easily, but that doesn’t make any sense.

      1. Temperance*

        I think what he’s saying is that Boss is seeking out sex as a transaction because his wife is too conservative to enjoy sex because they were raised religious in a sex-negative environment, so Boss needs to get some strange to satisfy his needs.

        1. Emi.*

          That’s … a lot of assumptions for him to make. But it sounds like a good interpretation on your part. :-/

          1. Temperance*

            I have shared this before, but I grew up in that community and I speak Evangelical pretty fluently. I have heard it all many times before.

        2. Troutwaxer*

          I wasn’t so much thinking “Boss needs to get some strange to satisfy his needs” as contemplating all the ways a fundie wedding night could be disastrous and leave one of the participants with lasting trauma, not so much any particular person’s fault as much as a result of ignorance. Maybe getting too off-topic here.

    3. Blue Anne*

      Uh, what? There are so many different judgments and assumptions in this comment.

      Are you suggesting that this guy sneaking out to escorts is a normal result of having a religious wife?

  50. No Name Poster*

    I totally understand why your curiosity was aroused. Mine would have been, too, and I’d have done the same digging.

    Now forget what you know.

  51. Lester*

    Where I work, the OP could report the boss anonymously to the Ethics & Compliance hotline. Even if he’s not “stealing time” because he’s exempt, he’s risking harm to the company’s reputation, and he’s engaging in behaviors that our company would not consider ethical.

    1. Jessie the First (or second)*

      I’d hate to work at your company. Sure, using work email to contact an escort isn’t smart (because it is not private). But I think you’d really have to stretch and stretch and stretch to think he’s risking harm to the company’s reputation. And we also don’t know that his company would consider any of this unethical (you have to assume he is cheating, which we do not actually know, and that he is paying for sex, which we also don’t actually know, and that the state of his relationship with his wife and his fidelity status matters to a company – which we also don’t know. Frankly, I really like to think that employers do not care about the states of the marital relationships of their employees).

      1. Temperance*

        Eh, I work at a law firm, and if one of our partners was making contact with escorts through his work email, it would be a Big Deal. The last thing we need is some sort of Carlos Danger-style public humiliation because of an indiscretion on behalf of one of our employees.

        1. Jessie the First (or second)*

          “Carlos Danger” – ha! In all fairness, though, I would think that most email contacts don’t reach Carlos Danger levels of inadvertent humor and humiliation? I am probably naive. :-)

    2. Kbug*

      My mind has been screaming because I’ve always worked in social services, so if someone was linking our company/organization, which did work with vulnerable populations, to illegally paying for sex, it would DEFINITELY be something I’d report. In fact, I think my handbook says I have to! Particularly if working with human trafficking or something. Just, no.

      1. Jessie the First (or second)*

        Ok, but – most jobs don’t relate to trafficking. Chances are, this is Random Business in Random Industry in which combatting sex trafficking is not the mission. Also, chances are the business is not, say, Catholic Charities – I mean, really, if the entire mission of the organization was in direct conflict with what this guy was doing, the LW would have said so!!

        1. Temperance*

          The snarky part of me wants to point out that the Catholic Church was actually the largest ring of pedophiles in history, so it’s really not outside the realm of possibilities. ;)

        2. Kbug*

          It doesn’t have to just be trafficking, though, that was just an example. if you’re working with any sort of vulnerable population, or somewhere that supports causes that work with vulnerable individuals, it shows even worse judgement and isn’t the type of conduct a professional should be displaying in that type of environment.

          Especially in a post Ashley Madison world- things leak, or police investigations happen. No one really wants their business name published in a list of clients of an escort firm.

  52. Kindling*

    I had something similar happen to me at an old job and I’m glad I didn’t tell anyone, but it is a good story, which I will tell here only because none of you would ever be able to identify the person in question.

    It was an admin type shift position where all the people in my role shared a computer. One day my co-worker and I had to make handover notes for the next people on shift, so we were skimming our internet browser history to jog our memory about what we did that day. We didn’t have to scroll very far before we saw someone had been browsing a gay hook-up site from the work computer. It was an almost all female staff, so we immediately thought of the only male who worked with us, but he was in a committed relationship and it didn’t seem like something he’d do. Some people on staff were mutual friends with his girlfriend, which added an awkward layer.

    Then we realized that the person had been looking for a certain collectible on eBay right before looking at the hook-up site, and put 2 +2 together because we knew who on staff collected that item. They were more senior than us and the times matched up to an event the night before that he worked. He wasn’t in a relationship as far as we knew so didn’t seem to be harming anyone. We marvelled about how someone could possibly not know about incognito browsing, shrugged, cleared the browser history, and decided to never speak of it again. I don’t think either of us have told any of our old co-workers to this day; I’ve only told friends who would never cross paths with the guy (and now you internet strangers who will also never know him).

    Anyway, I’m really glad I didn’t tell any of my co-workers and turn it into office gossip. It was a funny thing that me and one other co-worker shared and that was it. Tell an unrelated friend, laugh about it, and smirk to yourself the next time he goes off about how faithful he is.

  53. Yellow*

    As an EA myself, I would not ever acknowledge that I even saw this. A huge part of my job is discretion and trust, and my employer’s marriage has nothing to do with my job. I think the LW dug too far and should drop it, and stop snooping unnecessarily.

    1. Mirax*

      Agreed. My boss did some similar things back when I was a PA, and while I kept tabs on where he’d be just in case one day he didn’t come back (the idea of him getting in a car crash or something on the way to or from was a real concern, with how he drove!), part of what he was paying me for was my silence.

  54. Anon This Time*

    One of my long-ago bosses hired call girls all the time. Sometimes they came to the office (we had a bedroom) and I got to pay them! He took a shine to one of them (I knew because he told me things I did NOT want to hear) and saw her frequently outside of the office. I knew her name and phone number and her voice very well, since my boss wouldn’t dream of placing his own phone calls.
    Imagine my surprise when I go to my 10 year high school reunion and meet the fiancé of a schoolmate whose voice seemed very familiar. I asked her, “Are you Bonnie?”, and she replied yes. I then recited her phone number to her, and she was understandably puzzled. I then told her who I worked for, and she literally dragged me to the ladies’ room to beg me not to tell her fiancée. Of course, I didn’t. But, I did get photos of the two of us to show my boss.
    Fast-forward to my 20th reunion, and I see the same schoolmate. Asked him if he ever married Bonnie. He did and they were already divorced. I still didn’t tell him, because why? (I still have the photos.)

  55. sfigato*

    In a related note, I once worked with a young woman who was incredibly secretive about her private life, seemed to have more money than her modest position would provide, and was frequently traveling with “boyfriends.” She left, I got her computer, and found in her saved webpages a site called “escort support.” I didn’t dig any further than that, but it confirmed a lot of my suspicions.

  56. Nathaniel*

    It is also possible that he is doing outreach work with them, as some religious institutions are known to do. Or, he could be moonlighting as a vigilante against sex slavery. Or, he could be looking for companionship and true escort services. At the end of the day I would say it is really outside of the bounds of professionalism to look into this further.

    1. Temperance*

      That is really, really reaching. Have you heard of Occam’s Razor?

      I can’t imagine on what planet it would be a reasonable thing for a heterosexual dude to book prostitutes/escorts/call girls to try and preach to them. That’s what the gross men at my church would say they were doing when they were caught, though.

      I think buying sex on company time is unprofessional. She’s just doing her job.

    2. Observer*

      Sure. And I have a bridge to sell you.

      The last time I heard that line (through the family grapevine) the couple ended up divorced, and she got the kids and the support of his family.

  57. Ed*

    I have same situation but my boss is my brother and he owns the place. I understand his wife is a shrew and semi-psychotic. I mainly don’t understand how someone who is fanatic about health,dieting,etc. would risk catching something yuck from a sex worker. Even the best piece of steak can be hiding salmonella :)

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