my boss enlists me in hiding his multiple affairs from his wife

by Alison Green on January 30, 2017

A reader writes:

My boss is having multiple affairs. I am his assistant, so I know about all his visitors and his schedule. He is married, but he often has visits from two different women, and he outright told me to never tell his wife about them. When either of them visit, he locks his door and tells me he is not to be disturbed. This happens almost weekly.

He sometimes asks me to book local hotel rooms for an hour or an afternoon, and he sometimes buys jewelry and flowers for the two women he sees regularly. I know this because he sends me out to pick up the jewelry (which I later see them wearing) or asks me to have the flowers sent to them. He never does anything like this for his wife. One of the women just had a baby who is named after my boss and has his surname.

One time, his wife showed up for a surprise visit to take him out to lunch, and he directed me to lie that the woman who was in his office was there for a job interview. He also submits expenses from his business trips (where he has traveled alone) and I have to re-calculate everything because he has upgraded the company-provided hotel room to a better one on his personal credit card and bought breakfast for more than one person the next morning. When this happens, he tells me he had “company.” There was also an incident where he came to work panicked because he said he accidentally used his company credit card at a strip club. He sent me to retrieve it and pay his tab with cash, but the address he sent me to was actually a massage parlor.

Normally I honestly don’t care what people do in their own private lives, but I hate that I’m part of his lies to his wife. She is a nice person and she is dealing with a heart condition that just required surgery. I know they don’t have an open relationship because my boss lies to her and also directs me to lie to her about his actions. He says she can never know. I get sick whenever I think about what he is doing. I know a way I can out him to his wife anonymously. Do you think I should let her know, or is this none of my business and I need to stay out of it?

Ugh, your boss is a horrible sleazebag.

I hate that he’s compelling you to participate in his deception … not to mention sending you to massage parlors to deal with his tab (!). And he tried telling you it was a strip club, as if that was somehow going to make it okay to send you there?! He’s weirdly shameless about all of this.

As for whether you should anonymously out him to his wife or not … I don’t know. Without knowing her, neither of us can know whether she’s someone who would want to get that tip-off, or whether she’s someone who would be happier never hearing about it, especially while she’s in the midst of a health crisis. There are people in that second category, strange as it can sound to people in the first category. Ultimately, since you can’t know that and this is your boss, I’d err on the side of staying out of that piece of it. (On the other hand, this is all primed to blow up in her face, especially since he’s now apparently fathered a baby she presumably doesn’t know about. So … ugh.)

However, I do think that you can tell him that you don’t want to be involved in this anymore — that you’re not comfortable lying to his wife, visiting adult businesses on his behalf, or buying gifts for women who aren’t his wife.

There’s potentially some risk to your job if you do this, depending on how your boss reacts to this. (Some sleazebags would accept hearing this, although with one this shameless, who knows.) But if your boss isn’t the owner of the company, talking to HR — or his boss directly, if the company is too small to have truly functioning HR — before you talk to your boss himself could provide you with some protection if he does try to retaliate against you for opting out of his philandering.

Read updates to this letter here and here.

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{ 417 comments }

{ 417 comments… read them below }

  1. Violetta*

    I think you should out him. She already has health problems and he’s putting her at risk for STDs.

    (phone wanted to autocorrect STDs to skis, which would have been nicer)

    1. The Not Mad But Occasionally Irritable Scientist*

      Well, assuming they still have a sexual relationship – which they may or may not, and which OP doesn’t know.

      1. Violetta*

        I guess. The fact that he’s having unprotected sex with these other women (hence the baby) would be enough for me. In the wife’s place, I’d absolutely want to know.

        1. The Not Mad But Occasionally Irritable Scientist*

          Like I said below though: nobody has any idea what goes on in their marriage. I agree, but that’s just too hot a potato.

          1. Zooey*

            Yup. Telling the wife gets OP involved in someone else’s marital drama, and many people react to stuff like this with “shoot the messenger” syndrome. As much as we all feel bad for the wife, her relationship with her husband is actually not OP’s business, and could potentially jeopardize his/her personal safety.

            1. Dust Bunny*

              If nothing else, the wife is likely to find out when he’s on the hook for child support, if she has any interest in or access to their financial information at all. There is no way this shock is not going to get worse as time passes.

            2. Fortitude Jones*

              Exactly Zooey. OP needs to stay out of the boss’s marital issues and just put a stop to the whole lying for him thing.

            3. Not So NewReader*

              It happens often enough that when a third party intervenes between two people the two people turn on the third party. OP could end up in a bad, bad place.

              OP, don’t tell the wife. Just deal with what you see in front of you. That would keep me plenty busy just with that part.

          1. Leatherwings*

            But OP isn’t in a place to know whether that’s the case. This is a pretty huge assumption to justify what could be a pretty damaging (to the OP) action (telling the wife).

            1. Jamie*

              I don’t think it’s a huge assumption to think a married couple will have intimate relations at some future point in time.

    2. Leatherwings*

      I really sympathize with both the OP and the wife here. Anyone who has to interact with the slimeball boss, really. But the health of the wife just isn’t OPs responsibility.

      1. Violetta*

        I’m not saying it is, but if she’s already leaning towards telling her, that would be an extra motivating factor for me.

        1. Leatherwings*

          I truly don’t intend to argue, but I’m not quite sure what you’re advising OP to do here. You agree it’s not her responsibility to out her boss, but at the same time providing motivating factors to do just the opposite? I just don’t understand.

          1. Violetta*

            I’m saying it’s not ultimately her responsibility so if she didn’t feel like doing it, I would say that’s okay. OP seems to be thinking about outing him though, so if she’s willing to do it I think she should go ahead.

          2. Engineer Girl*

            Because you need to consider ALL the data before you make a good informed decision. Raising points the OP may not have considered is part of that decision making process.

            1. Leatherwings*

              Hm. I disagree with this a little bit, largely because all data is just speculation about someone elses’ relationship. It’s not verifiable “data” so it’s not going to do much good to consider it. There are a million different scenarios here OP could consider and weigh, but when it comes down to it, there’s no way of knowing what’s true, what’s likely, what’s not likely etc.

              1. Engineer Girl*

                Data isn’t opinion. Data is based on facts. Like that OP may be mischarging company time based on company policies. That’s worth checking out to see if it is true. To say that’s it is impossible to know what is true, what may be true, what isn’t true is a fallacy. I analyzed data and probabilities many times as a Risk Manager. Just because you can’t know the absolute 100% truth doesn’t mean you can’t get a pretty good idea of it.
                That’s what a good analysis is all about.
                That’s why the comment section is so valuable – it brings up scenarios that OP hasn’t considered.

                1. JB (not in Houston)*

                  But we’re talking about what Violetta characterized as “data,” like the boss putting the wife at risk for STDs. We don’t know what goes on between the boss and his wife, so that would be speculation, not data.

                2. Leatherwings*

                  No kidding. But OP (and commentors here) don’t get to and probably can’t determine the “data” around the bosses STDs, the wifes immune system, and the nature of their physical relationship. This entire thread isn’t about company policies, it’s about STDs and telling the wife, so that’s not was I was addressing at all.

                  And really, there are a lot of pretty smart people here. There’s no need to condescendingly define the difference between facts and opinion and explain what analysis is. Speculating about whether your boss is giving his wife an STD that she’s uniquely susceptible to isn’t data collection or science so please cease with that.

                3. Anonymoose*

                  Yes, data is fact if it can be corroborated. The “data” referenced above should actually read “possible outcomes of which we have absolutely no idea”. And therefore has no standing in any way.

                  However, helpful advice is always helpful.

      2. Stranger than fiction*

        True, but what if it blows up later and everyone realizes the Op knee all along? Doesnt that make her complicit?

        1. Jessie the First (or second)*

          But in this situation, “complicit” doesn’t matter – the wife is not her friend or family member so there is no personal repercussion. She may feel awful, and she can certainly choose to tell the wife, but the affairs aren’t her moral failing, they are the boss’s, and she is an employee, not a personal friend choosing to help lie.

        2. Adam V*

          Maybe, but you can probably get through it by by saying “he’s my boss, I felt like I had to do what he says, even if I found it distasteful” and people should understand that you were in a difficult position.

        1. Not My Circus, Not My Monkeys*

          Moguls can destroy the knees. Can I have a case of packed powder with a side of après ski-itis?

    4. Ann O'Nemity*

      I completely disagree. The OP shouldn’t be in the middle of this at all. Outing the boss carries significant potential professional risk and very little benefit.

      If the OP has other options – any other options – it’s time to look for a new job. Working for a slimeball like this is soul-sucking.

      1. Violetta*

        I agree she should look for a new job, or a transfer.

        It sounds like the boss isn’t particularly discreet though – imo, OP could comfortably deny having anything to do with the anonymous outing if asked about it.

        1. Fortitude Jones*

          It’s not going to be anonymous – that’s the point. OP would be the most likely suspect here if she did try to out the boss anonymously because she’s presumably the only one the boss is having buy flowers and jewelry for the mistresses, booking the hotel rooms, and paying off his massage parlor bills. The boss is an idiot, but I don’t think he’d be that dumb to know how this got back to his wife.

      2. Michelle*

        I agree, Ann. It’s best to stay out of your boss’s relationship(s).

        You many get some personal satisfaction outing a creep and a cheater, but it gets you even more involved. I would say find another job and get out.

      3. Working Mom*

        I would agree that looking for a new job is the best way to handle this. The entire situation is not going to end well for anyone involved, regardless of the outcome. I would simply get the heck out of there, and let sleeping dogs lie. The wife may be completely unaware, she may *know* deep down but is OK enough with turning a blind eye for now, or anything else at all. Really – there are way too many unknown factors to get any more involved at this point. I would cut your losses and get the heck out of there, and take the secret with you. At the very least – on your way out you could let the boss know that you are leaving because you are NOT ok with the position he put you in, but its none of your business so you’re out.

      4. mreasy*

        Look for a new job, but meanwhile, stop helping him. If you get fired for not buying his mistresses , you can file for unemployment and you have a case…or you can tell the boss you’ll be making that case, which will affect his anonymity, and get him to say you were laid off or not contest the claim?

      5. Not So NewReader*

        OP has no leverage, no vantage point in this mess. If she were the big boss my answer would be different. But as his subordinate, we have to consider that she is vulnerable to retaliation.

        My husband used to say, “When your hand is in the dog’s mouth you withdraw it slowly. The dog is in a position to hurt the person’s hand. Likewise with OP, the boss is in a position to fire her, give her a bad reference and so on. Whatever decision OP makes in the end, these will be things she needs to consider.

        1. Purple Dragon*

          “When your hand is in the dog’s mouth you withdraw it slowly.”

          I love this – I’m going to try and use it asap !

          1. Laura*

            Nope! You shove that hand as far as you can into the dog’s mouth to break its hold as the jaws are forced to open – up to the wrist, if you need to! Unless it’s a pitbull, in which case nothing will work but someone squirting water up its nose really hard. If you’re lucky.

        1. Koko*

          Who has his surname! Which suggests…she put his name as the father on the birth certificate? Wow.

    6. Engineer Girl*

      This is how a work friend found out about her husbands affair. She got a phone call from the Department of Health telling her she needed to be tested for HIV. Fortunately she didn’t get it.

    3. Karen D*

      and pretty quickly, too.

      The factor I see here is that right now, from a corporate viewpoint, OP is 100 percent complicit in Boss’s embezzlement. When he gets caught, OP’s fingerprints are going to be all over it and s/he’s going to be on the street especially if the company has any kind of formal or semi-formal procedure for going around an immediate supervisor to register a complaint.

      And yeah, it’s embezzlement, even if he “pays back” the monetary resources he uses right away. He’s also misappropriating OP’s time and effort, presumably while s/he is being compensated, and using company premises in a way that could foreseeably create legal and/or safety issues. This is a great big ball of “no bueno” and whether or not the wife is told, OP absolutely must come clean to corporate or forfeit the company’s trust.

      2. Jane*

        This is what I was trying to understand with my comment below. Is he using company funds to pay for these women’s meals or is he paying for upgrades/meals out of his own pocket. This was not clear to me from the letter. This is a critical issue as to whether or not the company will have an interest in what he is doing. Although they may be highly irritated about having his assistant lie for him, my guess is they would not be nearly as interested unless it involves misappropriation of company funds.

        1. Karen D*

          There’s at least one case (strip club/massage parlor) where he used the company card, and even if he sent poor OP over there with cash the very next morning, it’s highly likely that transaction will show up as a charge and then a refund. If he’s done it once, he’s likely done it more than once and just didn’t call on the OP to help straighten it out.

          It does sound as if, in many of the cases, he’s covering the portion of expenses related to his “companions” from his own pocket, but if OP is having to “recalculate” things that will become evident when corporate puts his expenses under a microscope.

          Helena had a really good point about possible contract audits as well. If a contractor is involved, that is another layer of fussiness with much less incentive to let things slide.

          1. JB (not in Houston)*

            You make some good points, but if he is covering the expenses himself, he’s not embezzling, right? I mean, I’ve worked in places before where you could put hotel room charges on the company card if your spouse or kids were with you, for example, but you had to repay the company when you submitted your expense report. If that’s what he’s doing, and that’s why the OP is recalculating, then he’s not embezzling.

            1. ZTwo*

              The thing is, OP doesn’t have to know for sure it’s embezzling to include it in a conversation with HR. She can just frame it like this: “There are also times when I need to recalculate the expense report because he [upgraded the room/bought someone breakfaster/whatever]. I’m concerned that handling them that way isn’t following policy or [is definitely against policy/will be confusing to the accountants/whatever. Can you clarify the process I should follow?”

              That’s not a perfect script by any means, but since embezzling/expense discrepancies can cause problems it’s worth her raising that issue with them, especially since it overlaps hiding the affairs and her job duties. Raising it doesn’t mean she needs to say it’s definitely embezzlement, only that she’s concerned about this specific job duty (in relation to everything else).

              1. JB (not in Houston)*

                Did you mean to reply to someone else, by any chance? I was addressing Karen D’s confident, unequivocal statement that the boss was embezzling (and that the OP would therefore be “on the street” if the company caught him). My comment wasn’t in any way taking a position on whether or not the OP can take it up with HR.

                1. drashizu*

                  It reads as a pretty sensible reply to your comment to me. Someone reading linearly down the thread will read “Go to HR!”/”But it’s not embezzling.”/”Ok, but whether it’s embezzling or not, definitely still go to HR, and here’s a script for how to do it without making an embezzlement accusation.” Which is a perfectly logical progression.

        2. yasmara*

          It sounded to me like (except for the strip club/massage parlor incident), the OP is having to sort out his expense reports to explicitly separate his personal expenses (room upgrades, 2nd breakfast, etc.) from legitimate corporate expenses. So while there is absolutely no argument from me that Boss is a total slimeball, he does not appear to be embezzling from the company unless you count the OP’s time/energy & the “office visits” by his lady friends.

          OP, find a new job ASAP if you can! I just can’t see this ending well for you…

          1. Natalie*

            I really doubt the labor hours would count as embezzlement – it’s not unusual or inappropriate to have your employee separate your business and personal expenses in an expense report. What exactly the personal expenses are doesn’t really change that it’s a perfectly legitimate use of employee time.

            1. Anna*

              This yes, but having the OP go to the strip club/massage parlor and give cash so they reverse the charge on his company credit card is all sorts of a problem with misuse of the OP’s time.

              1. Kimberlee, Esq*

                Eh, I would disagree. People sometimes use their corporate card by mistake. Its gross that she thought she had to go to a strip club to do the exchange, but she didn’t actually have to (happy endings aside, massages are perfectly legitmate expenses at many companies and there’s nothing inherently disgraceful about entering a massage parlor). I’m 100% on the side of “OP should find another job” but it sounds like OP’s role is not far removed from what many assistant roles are, just with a squick factor of knowing there are affairs happening. Sending your assistant with cash to reverse a personal charge is really NBD in a lot of companies.

              2. Natalie*

                I’m not saying it’s not gross or inappropriate. It’s just extremely unlikely to be *illegal*.

          2. RVA Cat*

            This. Does the company have an ethics hotline where you could report the expense & credit card issues?

            Seconding going to HR and/or the boss’s boss, also getting out of there ASAP. Do NOT out him to the wife, however you will want to document all this funny business with HR, and possibly with the legal department so they can prepare for the eventual subpeona from her divorce lawyer.

          3. Karen D*

            It’s actually embezzlement even if the money is paid back immediately. We had a local case where an executive at a local food bank was using the charity’s credit card to buy groceries, gas, etc. and writing the charity a check, usually within a day or two. Even with a reasonably plausible tale (she was using the card at the gas station so she could pay at the pump, etc.) she was arrested. She went through pre-trial intervention, so no criminal record, but destroyed her career.

            I was actually thinking of that case when I wrote my first post … the food bank only had two other employees, one of whom demonstrably knew about the misuse of the card, and that person was shown the door as well.

            1. Observer*

              The issue there is not really embezzlement, though. There are a whole raft of rules around the use of credit cards for non-profits, and she clearly broke those rules. Since the rules are primarily intended to avoid embezzlement, it may have been talk about as such, but that’s not really what it was.

              1. Trout 'Waver*

                In my mind, the slimeball realized he didn’t have enough money to pay his sex worker* and used the company card to pay so his wife wouldn’t find out. Even though he intended to pay it back the next day, it still technically is embezzlement. I would highly doubt he would ever be charged for it in this case, though.

                *Yeah, I know the overwhelming majority of masseuses aren’t sex workers, but I would bet that this particular one is.

            2. Koko*

              It’s very common where I work for people to, for instance, book a hotel room for 4 nights when the conference only requires them to be there for 3 nights and put up their own funds to cover the 4th night. (As a way of getting a one-night vacation without having to pay for getting there and back.) Or to charge a meal to the company card but cover the cost of the bottle of champagne they bought which wasn’t a covered expense. Or to book a flight to a third location instead of back home at the end of the conference and pay the company the difference between the flight home and the flight to the other location. None of that is embezzling. Sometimes you can’t use two payment methods and the company would rather float an employee expense for a couple of days than require the employee to float a business expense. The purpose of the expenditure is still primarily business.

              I do think there’s a difference however between that and just charging non-work expenses like gas and groceries to a company card (a nonprofit no less!). That’s basically using your position as way to get a line of short-term credit and would be a pretty serious ethical breach. It sounds like OP’s boss only did that once, though, which he claims was an accident. As long

            3. Jeanne*

              Some companies have policies allowing you to use the card and pay it back. Others don’t. My sister is allowed to do some purchases on the company card if she settles it when the bill comes. We don’t know their policy.

          4. Karen K*

            Yes, not that it makes it all better, but the boss seems to be very cognizant of what is appropriate for the company to pay for and what isn’t. Hence the OP having to sort out expenses after trips where he had “company.”

            So, although he may be a major slimeball, at least he’s not an embezzler, and the OP is not breaking any laws that I can see.

            That being said, the question is, what to do now? Honestly? I don’t think I’d tell the wife. My position is that I work for the husband/company, not the wife. If I felt that I could not continue to do what he asks, then the answer is to leave the position. In this case, even if I was his personal assistant, I’d find some of the things I would be asked to do repugnant.

            I would never forgive him for the strip club/massage parlor debacle. That was downright heinous. Sounds like it was the tipping point for the OP as well.

          5. Marisol*

            That’s the way I read it. I process expense reports for my bosses, and occasionally have to separate the co-mingled charges because, say, he bought dinner for friend while traveling, put it on the same tab as his meal, but doesn’t want the company to pay for that friend’s dinner. There was some ambiguity in the wording but I don’t think what the OP describes is necessarily embezzlement.

            1. Engineer Girl*

              Don’t you think that the number of hours charged to this has something to do with it? If it were an occasional thing then it’d no big deal to the company. In this case it is pervasive and OP is regularly spending hours fixing things. At that point it becomes misuse of company resources for private things. It would also be classified as mischarging, as the hours are not being used for company related interests.

              1. Marisol*

                It may have *something* to do with it, but I have a feeling it wouldn’t matter too much how many hours the assistant is spending on revising her boss’s expense reports. In my experience, assistants are often charged with handling all kinds of personal tasks. If that’s the case in the OP’s firm, then there’s no material difference between say, researching caterers for a private party the boss is having (a task which could take several hours) and doing the math on a hotel folio to separate the price of a room upgrade. It really depends on her job description I would think. Also, I doubt the extra work the OP is doing is all that time consuming. If all she’s doing is calculating the price difference between what is allowed versus what was spent, then it takes as long as it take to input numbers in a calculator–an extra five minutes at most. My guess is the OP mentioned it because it’s onerous, and especially distasteful given the reason for doing it, rather than time-consuming. But I am speculating of course.

                1. Jeanne*

                  I think you are right. I think she mentioned it more in context of how she knew he was cheating on his wife and that it was icky. Not that he was stealing money or resources or her time. If she does the statement every month, it would take very little time to do the math.

        3. Anonymous*

          It says that he used his personal credit card, so it sounds like the hotel room was reserved by the company, but he paid for it and the upgrade and then is supposed to be getting reimbursed for just the originally reserved/allowable rate, which is I think what OP is saying when she says she is recalculating it, i.e. calculating the allowable portion. Generally that’s fine, although it’s nuts that he’s doing this for such purposes and making OP do the recalculations on his expenses for such a reason.

      3. Lora*

        THIS.

        It’s one thing to accidentally use the company card for a personal expense. I spent a full YEAR trying to sort out the day I used the company credit card at the grocery store – and that was when I realized my mistake right away and the grocery store reversed the charge and put it on my personal card the very next MINUTE so it was obvious what had happened. And the next day I bought a wallet with more compartments so I wouldn’t mix up my blue plastic cards by accident again. That’s an accident and it caused an accounting snafu because it came up in SAP as two separate things ugh ugh ugh and one was listed as “meals” in Concur and the other was listed as “unknown expense” and because it was Unknown it wouldn’t let me combine the things and it took an admin, a Corporate Finance person and an auditor a friggin YEAR to fix and in the meantime I got constant auto-generated reminders that I suck at life and was violating all the company policies ever. That’s what an accident looks like.

        Then there was the day that I couldn’t remember the last name of one of the clients who was visiting and the auto-populate thing wouldn’t let me just put Jose on the Guests At Business Meal list and it looked like I spent more than the limit per meal on a business entertainment expense report and that generated a bunch of “you suck at life and you violated company policy” mail too.

        There was also the day that the exchange rate changed by $0.005 between the time I was billed by the hotel for parking and the time the receipt was actually imported into the system and Concur wouldn’t let me submit it because the electronic receipts didn’t match up and clearly I was defrauding the company by $0.02.

        I’ve done my share of expense reporting screw-ups. These are things an auditor will be like, “yeah, stuff happens, it’s cool”. This crap your boss is asking you to do? NOPE NOPE NOPE. They will have zero mercy.

        1. BananaPants*

          I have experienced the same frustrations with SAP and Concur!

          I was traveling for work once and had to use my corporate card for a personal entertainment expense because I was in Europe with pre-chip credit and debit cards, and my corporate card was the only one with chip + PIN. Handling even a normal expense report with a few personal expenses separated out is a pain in the neck; it must be a mess for OP to have to deal with this on behalf of the sleazeball boss.

        2. Amber T*

          I know there’s a lot of argument against making employees use their own credit cards for business purposes and reimbursing them later, but this is the exact reason why my company has one corporate card with very, very few people that have access to it. My industry is particularly sensitive to how expenses are made and are coded (LOTS of bad stuff can happen if we don’t allocate a charge correctly, let alone pay for something personal). Expense reports probably make up about 40% of the admins workload, because it’s that super important. I feel like it’s a right of passage for all the newbies (of those workers who travel) to lose a receipt and not be able to get reimbursed. It sucks, but the alternative is potentially losing their job/other people’s jobs/losing clients/maybe jail time?

    4. Jadelyn*

      Seriously – I’d really urge the OP to go to HR, because ordering a junior employee to go to a strip club and/or massage parlor (honestly, it’s not really much less worse if it actually *was* a strip club) could well be the start of a hostile work environment claim. Not sure it, by itself, would qualify, but it strikes me as the sort of thing that’s close enough for a labor attorney to start shit with the company over, whether or not they would ultimately prevail.

      Not to mention, you know. Being ordered to lie for the boss while he’s quite possibly having sex with his mistresses in his office at work???

      Just saying, as HR, if something like this were happening at my org we would so much rather the employee tell us sooner rather than later so we can step in and do something, or pass it along to someone higher up who can step in.

      1. Purest Green*

        Not to mention, you know. Being ordered to lie for the boss while he’s quite possibly having sex with his mistresses in his office at work???

        Yeah, that part is particularly appalling to me. I’m surprised this guy hasn’t stepped on his own…you know…with both his wife and at work.

      2. Not So NewReader*

        I am seeing a progression of things getting worse and worse. OP, you have put up with more than enough already. Do what you have to do to protect yourself, this probably means get the heck out of there.

  3. LittleLove*

    Visit the Chump Lady/Chump Nation site. She will give you clear direction on how to tell the wife and why you should tell the wife. Women is harsh but honest and supportive.

    1. MindoverMoneyChick*

      I second this – she is awesome and has really changed my perspective on the tell/don’t questions.

        1. OhNo*

          I only read it briefly, so perhaps a long-time reader can summarize it better, but it seems to be of the “cheaters don’t change, preserve your sanity and leave them” variety of advice. Sounds pretty accurate in this context, but it’s hard to know for sure.

          If nothing else, maybe the OP can recommend the site to the wife. You know, as “interesting reading material” while she’s recovering from surgery.

          1. eplawyer*

            Recovering from heart surgery is not the time to be reading advice about adding stress to your life. Even if the end result is less stress.

            The boss’ personal life is none of the LW’s business. She needs to stay out of it. That means no more covering for the boss. It also means not telling the Wife. It is not part of her job duties to tell the Wife her husband is cheating. It is not part of her job duties to order jewelry for the girlfriends.

            She needs to go to HR and the Boss’ boss because it is part of her job duties to make sure personal drama doesn’t blow back on the company.

        2. Yep, me again*

          Alison,

          If she were somehow terminated (dunno if that would be applicable here) or found herself looking for a new job, what would she tell perspective employers?

        3. MaybeTomorrow*

          Her advice is to tell. It gives the chump (her word on the site for the spouse being cheated on) the ability to take back control over their own life and not be stuck.

          The spouse is endangering her health and obviously doesnt give a crap if that were to add to the current health issues.

    2. Temperance*

      I have tremendous sympathy for Chump Lady and agree with her advice wrt telling personal contacts, but LW could very well lose her job and/or get a bad reference going forward. She needs to consider whether the deep personal cost is worth helping this nice lady who is an essential stranger.

      1. The Strand*

        I agree. Perhaps OP could wait until

        A. Wife has recovered fully (month or more) from surgery.
        B. She has a new job.

        That doesn’t mean she can’t clue in HR about something egregious happening.

        1. Jennifer*

          I think no matter what OP shouldn’t even consider telling unless she’s out of the job. I honestly don’t know whether or not she should tell (for example, if the marriage is what’s keeping the wife in health insurance), but she will be screwed if she tells while she’s still employed there.

  4. orchidsandtea*

    Whoa. So, if he’s not the owner, this is a MASSIVE misuse of company resources and his boss may be Very Interested. And framing it that way may be the least-awkward way for you to approach his boss. “Ferdinand, there’s a business issue I wanted to bring to your attention. Fergus has been using company resources in X, Y, and Z ways” (note: include your time in this) “and I wanted to get your take on it, as I’m uncomfortable with this.”

    2. AndersonDarling*

      I’m not 100% sure, but if this a publicly traded company, using the company time/money for sexual encounters could be fraud.

      1. Helena*

        And if the company is paid by federal money (through government contracts, for example), getting caught using company time like this will bring down MASSIVE TROUBLE from the Feds.

    4. Ann O'Nemity*

      I’d still start looking for a plan B / exit strategy.

      Telling HR, big boss, or even the ethics hotline could potentially backfire on the OP. Anonymity isn’t guaranteed. And even if HR doesn’t specify that OP is the complainant, the boss may suspect OP anyway.

      1. Karen D*

        Not telling carries much bigger consequences IMO. OP has a duty to the company to report something like this. If corporate finds out and OP hasn’t been forthcoming, s/he will be seen as just as untrustworthy as Boss.

        1. Natalie*

          I’m not sure about that last part – I think (or would hope) most companies would understand the power differential between someone and their admin and wouldn’t consider them equally complicit.

          1. Engineer Girl*

            If they have an ethics hotline where you can anonymously report? No. They’d say that you had a safe way to tell and didn’t.

            2. Anna*

              It would be naive in the extreme to believe that the ethics hotline was anonymous when dealing with something this personal. If you are the only person who knows something, there is no way to anonymously report it.

              They might mention the ethics hotline and ask why she didn’t use it, but no reasonable company is going to consider OP “as untrustworthy as the boss” in this scenario for not using it.

          2. OhNo*

            I mean, you’d hope so. But there was that letter here a while ago about someone who got fired for exposing a direct report’s time card fraud, so it may not be as cut and dry as we would hope. Better to err on the side of caution and report it now.

        1. Ann O'Nemity*

          Or the big boss doesn’t care? Or is too weak to do anything about it? Or, or, or…

          I’m similarly cynical that reporting this is going to be the silver bullet fix for the OP.

          1. myswtghst*

            I don’t think it’s a silver bullet or a fix, but I think it’s a good (and potentially necessary) step to take.

            1. OhNo*

              I think of it as more like a flow chart. Telling someone higher on the food chain is basically step one. From there, how things shake out depend on a lot of other factors that OP doesn’t really need to worry about yet.

      3. The Cosmic Avenger*

        Yes, but as others have said, the OP’s job could be at risk by actively covering for her boss’ fraud without reporting it. But a Plan B would be good to have before going over his head.

        And if the philandering, sleazy jerk IS the owner, then if the OP’s job is threatened over this, she could always point out that while she has a job she has a motivation to go along, but that motivation completely evaporates if she’s fired.

    5. Clear the ball*

      I like this. There’s a difference between being an admin and personal assistant. Seems like boss is treating her like the latter, and owner may not like it.

  5. Summerisle*

    Wow. This is beyond belief! I’m so sorry, OP.
    Tempting though I’m sure it is to out him (and though he deserves it), treating it as a purely work-related issue and talking to your boss and/or HR is probably the way to go. I would also be job hunting like mad, but that’s the OP’s call.

  6. Temperance*

    I don’t think there is a way you can anonymously inform her that her husband is a dirtbag without it coming back on you. You’re the person who knows his schedule, and who knows that he’s cheating on her with these other women, and it will be very obvious to him that you told her. He doesn’t sound nice or reasonable, so I think you need to protect #1 before thinking about doing anything else.

    My advice would be to find a different job. Admins are needed everywhere, you don’t need to work for a skeezer like this clown. I’m also wondering why no one at your company has caught that he’s using work funds to pay for “massages” and strippers.

    1. The Not Mad But Occasionally Irritable Scientist*

      This. Do not imagine the boss won’t guess where the anonymous tip came from.

      1. Jwal*

        And even if he doesn’t know that it was the OP, if the boss is the type of person to blame other people for the wife find out (as opposed to, you know, him being at fault for actually having an affair) then he might well put blame on the OP anyway. It’s easier to be mad at other people than admit you’re at fault sometimes.

        It’s a crummy situation to be in =/

      2. wrafreru*

        Exactly and, if asked point blank, could you lie convincingly or would you fess up? Even if you could lie convincingly, my guess is you’d always be on his list of suspects.

        Years ago, a friend got an anonymous text, something like “Do you know what your husband’s up to?” or something similar. She never did find out who sent it, but when she confronted her husband, he immediately confessed to an affair. I think wondering who sent the text really gnawed at my friend for quite awhile.

    2. Ann O'Nemity*

      I agree. The boss will likely suspect the OP no matter what. Even if the OP sends an anonymous email to the wife, they’d be the likely suspect.

    3. The Bimmer Guy*

      That’s true. In the meantime, because I agree with Alison that the LW shouldn’t tell the wife, the LW’s three go-to words should be “I don’t know.”

      Wife: “I’m here to surprise Jerry for lunch. But his door is closed. With whom is he meeting?”

      LW (Realizes he’s being intimate in his office with another woman at that very moment): “I don’t know…but let me see if I can find out when he’s free…”

        1. LSP*

          I’d expect that once OP tells her boss she’s not going to cover for him any more with his wife, that he may have enough sense to stop bringing them around the office.

          I realize, of course, that’s giving a lot of credit to someone who a) doesn’t know the difference between a strip club and a massage parlor, and b) isn’t bright enough to know NOT to use the company card there.

          1. Temperance*

            My thoughts on that incident are that he was at a rub-and-tug massage parlor, and thought telling his assistant it was a strip club would make him look a little better.

            1. OhNo*

              Then he’s a bit dim. Obviously the OP was going to figure it out, given that she had to go there on his request. (I’m still a bit in awe that he thought that was okay in any way, shape, or form.)

          1. Honeybee*

            This was my thought as well – I don’t think you can. The OP is trying to keep her job so she can feed herself and keep a roof over her head. Boss man can do what he wants – her job is to try to stay out of it as much as possible.

      2. D.A.R.N.*

        I don’t know if something that makes the LW look bad at her job would be a good idea. Maybe another variation could be just describing the person without the lies? Like, if one of the women is from X company, say “Name from X” instead of whatever lie the boss wanted?

      3. OhNo*

        At that point, OP might as well be a more general version of honest. “He’s meeting with a woman,” or “He’s meeting with a friend.” And then, if pressed, “I don’t know her name/company/the purpose of the meeting. Let me check his calendar and see if it’s there. “

        1. CanCan*

          Strictly speaking, the wife is not entitled to know who he is meeting with. She doesn’t work at the company, so why should she know who company employees are meeting with. The OP could just say, “He’s not available. I will let him know that you came by.” And if the wife asks who he’s meeting with, just insist that you’re *not able* to tell her (which can be interpreted as “don’t know” or “not allowed to”).

          1. OhNo*

            True, but that’s a little more context dependent. If the OP is or has been pretty forthcoming, suddenly refusing to talk about this one specific meeting could be the equivalent of hanging a banner that says “your husband is doing something he doesn’t want you to know about!” (I’m not saying that’s a bad thing, necessarily. But it’s worth keeping in mind.)

      4. Rater Z*

        I’m the kind of guy who would simply say it’s not a business meeting but just a friend who stopped by. I’ll open the door and let you join them.

    4. Stephanie*

      Yeah, I don’t really believe anything’s anonymous at work (perhaps I’m too cynical). I just have heard too many stories about “anonymous” employee engagement surveys being traced back.

      1. drashizu*

        The only form of anonymity I’ve ever seen was anonymity that came from secrecy. Someone leaving an unsigned typed note on someone else’s desk while they were out of the office, for example. You’re not anonymous at work unless no one knows it was you.

  7. Mike C.*

    Holy crap. First off, I’m really, really sorry you have to deal with this!

    Secondly, you have a lot more power here than you think you do. Though you’re not interested in doing this, in requesting to be kept out of these sorts of activities, the implication is that you’ll rat out your boss if things don’t change. So be firm and go for it.

    1. Artemesia*

      Yes. Being forthright about not participating has the implicit threat that you know things that would hurt him and so if you only want to be removed from having to deal this is the way to go. If he is not the owner however, then going to the boss or HR is also a reasonable things to do if you think they are not part of the same boy’s club.

    2. LBK*

      The OP pretty much has all the power here – if she says she’s not participating anymore and he threatens to fire her, she can remind him that if she’s fired then she has nothing left to lose by telling his wife. Her keeping her mouth shut can remain contingent on him keeping her employed but out of his affairs. I wouldn’t normally encourage playing games like this but when the relationship has devolved to one that’s much more personal than professional at this point I think it’s fine to play a little dirty.

      I’m also curious if this would qualify as sexual harassment, although since she’s not actually being made to see or hear about the sex acts and is just setting up the time and place for them, I’m not sure it would.

      1. Jadelyn*

        I don’t think it would for the setting up trysts part, but sending an employee to a sexual environment like a strip club/massage parlor could.

        1. fposte*

          She just dealt with the front desk, though. If merely setting foot in a strip club was sexual harassment, it would apply to everybody who handles the books in a strip club. I think it was unwise and that competent HR would at the very least insist it not happen again, but I don’t think it rises to the standard of harassment. (If he decided to have her make his appointments, though, that would be another matter, and she wouldn’t even have to set foot in the place for that.)

          1. Emilia Bedelia*

            I don’t think it’s the “setting foot” that’s an issue, it’s the making the employee do so. Especially since he seemed to be trying to cover up the actual nature of the place.

            If I were the employee, I would be scared to be associated with someone visiting a massage parlor for potentially illegal reasons. Even if the OP is just handling the money part, I would be very wary of getting caught and being associated with prostitution.

            1. fposte*

              I’m not saying it isn’t icky and there could be consequences; I’m just saying that a one-off to clarify finances isn’t likely to get the EEOC particularly interested.

        1. ouchie*

          Not to mention illegal.

          I’ve had clients prosecuted for this. It’s the legal definition of blackmail in my state.

          (Yes, I am a Lawyer)

        2. Mike C.*

          Note that I never said anything about blackmailing or threatening to blackmail the boss.

          I’m only pointing out that the threat is implicit and that the OP has more power to make changes directly than would normally be the case. That’s it.

          1. Marisol*

            The comment refers to LBK’s comment nested below yours. Although, an implicit threat could certainly be construed as implicit blackmail.

              1. drashizu*

                Now I’m curious – if implicit blackmail is a thing, and if it relies on the boss’s interpretation rather than the OP’s intention, how can she ever ask for or try to negotiate for anything at her job without risking being seen as blackmailing him? I would encourage the OP to go to HR no matter what else she decides to do.

                1. Greg*

                  I was wondering about that, too. I’m no lawyer, but it seems like there should be a distinction between explicitly asking for something of value (“Give me a raise or I spill the beans”) vs. using the information to forestall any retaliation (“I’m quitting and if I ever hear word of you bad-mouthing me to HR, just remember what I know”).

                2. Not So NewReader*

                  Why not just say, “I can’t keep track of your social calendar any more. I have too much else to work on here.”

                  There does not have to be a threat. OP could say this in a tired and dejected voice. It would sound benign as far as threats are concerned. If she is tired and feeling overwhelmed, that is separate from anything else that is going on.

                  I just wanna know, OP, how do you have time to do your job? This guy and his women have to be full time work.

              2. Marisol*

                I think there is always an implicit understanding that if an employee doesn’t like her employment conditions, she may quit. That is what gives an employee leverage in negotiating. Any employee can ask for anything knowing that the chance for fulfillment of her request depends on how much leverage she has in that regard. This applies to the OP requesting to be kept out of her boss’s (marital) affairs.

                I just re-read your comment and I was probably overstating it by calling it implicit blackmail; still I don’t like any insinuation of any threat to tattle. Instead of keeping the OP out of the fray, it pulls her in. Maybe you were referring to what would occur in the boss’s mind rather than anything the OP would signal, but in any case, the implication that she’ll “rat her boss out” just doesn’t sit well with me.

                1. Marisol*

                  and I just made up that “implicit blackmail” term off the top of my head, thinking aloud–I am not saying it is a thing that exists.

                2. LBK*

                  Saying that she should remind him is probably a step too far; I mostly meant to give a confidence boost to embolden her to make the request to keep her out of it, because ultimately she does have the power in the situation. She doesn’t need to make that explicitly clear to the boss, but if he thinks about it for 2 seconds he should realize on his own that he probably doesn’t want to piss her off by retaliating given everything she knows.

                3. Anna*

                  I’d agree with it pulling her in. At the moment, she’s following orders without complaint. The boss doesn’t have any reason to believe she approves of his activities or will do anything REALLY outrageous for him. Whereas if she starts implicitly or explicitly threatening to rat him out, she’s become an active secret keeper.

                  It’s the difference between “Jane isn’t stupid, she knows about my affairs, and she carries out my orders as part of her job” and “Jane and I have a mututally beneficial understanding: she scratches my back, I scratch hers”.

      3. Stranger than fiction*

        I would think maybe it does. If he’s having sex in his office and making her lie to people when they come by and that makes her uncomfortable…

    3. fposte*

      One of my “amorality is contagious” fantasies was that I would only agree to continue performing these coverup services for a substantial salary raise.

        1. fposte*

          Probably not a way I’d choose to do in real life because it does come close to blackmail, but I do think it’s an appropriate fantasy. And I think Loverboy is going to run into somebody with that exact thought one day, and either they’ll blow up in mutually assured destruction or they’ll be soulmates.

  8. Leatherwings*

    I don’t think you should tell her. It’s just not your responsibility to manage, as awful as it is. I’m always one for not sticking your nose where it doesn’t belong if at all avoidable. I realize your boss has involved you in this unwillingly, but getting involved in his marriage is something else entirely. I hope you’re looking for a new job, because this guy sucks.

      1. Leatherwings*

        No. Throwing a grenade into a room just because you won’t be there to clean up the debris is not right.

        1. Observer*

          The thing is that she IS involved in his marriage, whether she likes it or not. And, it’s not her problem to “clean up the debris.” The only reason I am hesitant to say that she should let the wife know is that I think that Alison is correct that some women just don’t want to know.

          1. Leatherwings*

            Yeah she’s involuntarily involved now, and OP should work to get out of that situation as quickly as possible, not get herself deeper into the situation. It’s certainly not her problem to clean up the debris, and I never implied that.

          2. Rater Z*

            The Law of Unexpected Consequences….

            We know the wife has had heart surgery. We don’t know if she was working, if she will be able to work again (depending on the surgery and its causes) and who is covering the insurance fees/costs for the wife.

            If OP blows up the marriage, the wife could wind up destitute and no way really to support herself and their children if any. I’m sure Indiana (where I live) is not the only state which does not provide for alimony, though some maintenance support might be provided. And look at the statistics of how many men eventually stop paying child support. It’s gotten better but not enough.

            I think the only thing is to talk with HR depending on what that department is like.

        3. Irene*

          I disagree. I think LW should not say anything, because she isn’t responsible for the wife and there’s a really high chance it will all blow back on LW, and likely cost her her job. However, once LW isn’t in that position anymore, she should speak up, because the boss is probably exposing his wife to STDs and the LW does know about it – not matter that she doesn’t want to.

      2. Marisol*

        If she poisons the relationship with her sleazebag boss, she may lose any chance of getting a good reference from him in the future. That could be an important thing to take into account.

    2. Engineer Girl*

      OP didn’t stick her nose where it didn’t belong. OP was dragged into it without her consent. OP could lose their job based on how the company finds out (and they eventually will).
      That changes the dynamics considerably.

      1. Leatherwings*

        Dude, I said as much already. I feel like this comment was pretty clearly addressing whether OP should tell the wife.

  9. Cambridge Comma*

    You might need to think a couple of steps ahead, though — telling the wife may not stop the behaviour.

    1. Just Me and My $0.02*

      But her obligation here isn’t to make him stop. She needs to inform someone with authority over him that he’s misusing resources and company time, and if no such person exists (because he owns it and it’s small), to let him know she has ethical concerns about being involved to help cover it up.

      1. Cambridge Comma*

        It sounded like OP would like the behaviour to stop and her tasks in the office related to it to disappear. Telling the wife as a route to achieving this may not work.

        1. OhNo*

          You know, that’s a good point. If the ultimate goal is for this nonsense to stop, that requires a different approach rather than telling the wife. Making it stop is probably going to require consequences outside of the marriage.

  10. Former Retail Manager*

    OMG!!!! I am so sorry you’re in this position. I am inclined to say that there will likely be consequences if you refuse to perform these activities for your boss anymore and I’d definitely talk to HR before standing up to him. However, I’d also be surprised if someone higher up the chain (although maybe not HR) isn’t already aware of his behavior and doesn’t care as long as he does his job well. This sounds like behavior that has been going on for a long time.

    Also, if the health issue weren’t in play, I’d personally out him to his wife, but considering the health issue and a heart condition no less, I’d leave that alone. God forbid the wife get the news and her heart give out or she have such a severe reaction that she needs to go back to the hospital.

    1. The Not Mad But Occasionally Irritable Scientist*

      Nobody really knows what goes on in a marriage except the participants. It’s a spectacularly bad idea to insert yourself into that.

      1. Newby*

        The only case where I could see telling the wife is if she asks. Then you know that she wants to know.

      1. sunny-dee*

        If she has serious health issues, she may not. It’s easy to be so tired or involved in other things (doctor’s appointments, therapy, medication / treatments) that she simply doesn’t realize it. Or is chalking any distance up to the stress of her condition.

        One other thing to consider … if she has serious health problems, now may not be the time to end their marriage simply because of the medical insurance.

      2. Payroll Lady*

        I agree Jenbug. Had a friend years ago who’s father was cheating, he outed him to his mother and then found out she had known all along and the parents had pretty agreed to stay together for the kids UNTIL this happened. She could deal with it as long “no one else” knew.

        1. Bwmn*

          100% to this. I know someone who’s parents “stayed together for the kids” throughout their high school years. When they finally did divorce, and this friend told her mom that she always knew, her mother was absolutely mortified and devastated. She really thought this was the best thing to do for her kids and though this would make them happy. Whether or not it was the good for the kids – who knows – but it was a decision she was actively making.

          Depending on what this woman’s health outlook is and what her financial situation is – having this information may easily just force a decision she’s not interested in making. If she herself doesn’t work, there may not really be other options for her to have health insurance if she leaves her husband – not to mention the stress of a legal battle. And while a potential STD would be incredibly unfortunate at this time – unlike speaking up about a drunk driver, the majority of STD’s are not life threatening. While an HIV/AIDS complication with a pre-existing illness would be greatly unfortunate – one just hopes that that as she’s receiving a lot of regular medical attention that staff may pick up on a dramatic change that might be HIV/AIDS. Provided of course, the OP’s boss and his wife are still even having sex – which they very well may no longer be doing.

          1. BeautifulVoid*

            +1 to all of the second paragraph. Regardless of whether she knows or just strongly suspects, this is not a good time to be rocking the boat, especially with regard to the health insurance issue.

      3. Observer*

        That’s not really true, and that kind of stereotype is often very damaging to the wife.

        A while a go there was a major scandal with a Rabbi who was atrociously abusing his position and doing stuff that, in some ways, makes this guy look good. When the news broke, there was a lot of finger pointing at his wife. Everyone was assuming that she MUST have known, and how could she NOT have known etc. It was really awful. And I totally believe her that she had no clue.

  11. The Not Mad But Occasionally Irritable Scientist*

    Welp, if anyone needs me, I’ll be in the shower, scrubbing the secondhand sleaze off with an economy-size jug of GoJo.

    I think you need to separate your moral outrage at what he’s doing from the moral hazard of doing things like lying by commission, paying his whorehouse tabs, and buying gifts for his partners. Fundamentally, his marriage just isn’t your business, and while she’s a nice lady, you have no idea what their arrangement is, and it’s not your responsibility to notify her. Stay out of their business and their marriage – seriously.

    But you are on completely fine footing telling him that you’re not going to lie to his wife (though you may have to compromise on lies of omission), you’re not going to shop for his affairs, and you’re not going to any more strip clubs, ever. You’re in a wicked tough spot, because someone with this level of poor judgment may very well retaliate against you for not helping him. But that’s making you do things you find morally repugnant. He can wallow in the filth if he wants, but you don’t need to scrub his back.

    1. F.*

      I second everything the Scientist says, but would also add: polish off your resume, you’re going to need it.

      Many years ago, when I was still young and naive, I was in a similar position with a boss, though not quite as deeply. Disabled wife, marriage in name only, blah, blah, blah… I had no idea whether he was telling the truth or not. I did not out him to his wife. There was no way that was going to end positively for me. They are still together and well into their 90s now.

      Although the sleeze factor is high, if it were I, I would not push back at this late date. He isn’t going to change, he is just going to find another EA willing to help him cover his tracks. He has enough on you for helping to alter his expense reports and other activities on the company time and dime that he can throw you so far under the bus that there is no recovery. All pushing back is going to do is probably get you fired and definitely get you a bad reference from this boss. Get out now while you can still get a good reference and find another place to work where you are not asked to compromise your morals.

    2. Lady Blerd*

      IA she shouldn’t tell the wife although I know several situations where the spouse was informed via an anonymous tip off. His marriage is his business and besides, I wouldn’t be surprised if one of the women, likely the baby mamma, will inform her but this is going off topic.

      On topic, yes, level one is telling him you won’t be covering for him anymore, that is abuse of power on his part. If he retaliates, go to HR or his manager with documented incidents if possible. And yes, be ready to find work elsewhere.

    4. DoDah*

      A Sales VP I used to work with used to conduct affairs on the road and with members of his own team. One of his (jilted) staff called the wife and told her. Wife called the CEO and had a nervous breakdown via phone. Long story, short. Wife forgave husband, the husband was promoted to SVP and the staff member who told was fired. Wife now travels with husband on all company trips AND the company pays her way.

      1. J.B.*

        SO messed up. Although goes along with my expectation that if there’s hanky panky going on, generally the younger female employee would be the one fired (at least without legal protection).

  12. Jesmlet*

    This totally sounds like the plot of some LifeTime movie… I think if it were me, if there was no formal HR department I could go to, I’d start looking for a new job and once I found one, I’d tell the wife or help her accidentally find out. You have to think of yourself too and there’s a lot of risk to your job if you refuse to be complicit or out him in any way. Also right after heart surgery is probably not the ideal time to hear this news (not that there is an ideal time). This just all around sucks and there really isn’t a good solution because either way, somebody gets hurt.

    1. Michelle*

      I am thinking that if the sleaze has no problem getting OP involved what’s to say he wouldn’t retaliate even if she was working elsewhere, if she accidentally helped the wife find out? There’s no hint or mention of violence in the submission but, I think finding a new job and getting away from the situation is best. That’s a ticking time bomb and I would not want to be anywhere near it when it explodes.

      1. Jesmlet*

        Yeah I guess I agree. Thinking purely from OP’s point of view, take care of yourself and get a new job and get settled there. No sense putting your career at any further risk for this guy.

        If I were the boss’ wife, I would want to know and that’s probably what I’m projecting in my original comment.

    3. AnonMinion*

      Have we already met the Worst Boss of 2017?!

      OP, I am so sorry you are going through this! How awful! Run, don’t walk, from this job!

    4. Not So NewReader*

      OP, I think there are enough people involved here that someone will tell the wife, if they haven’t already. Remember we don’t know if there was a trigger for her heart event. Maybe someone did tell her and she is just biding her time before she pounces.

  13. Construction Safety*

    Ugh.
    I’m leaning toward that he’s not the owner b/c of the corp/personal CC kerfuffle. If that’s the case, the OP could be collateral damage when the merde hits the ventilateur.

  14. But what about . . .*

    Who’s to say the wife doesn’t know? Everyone is assuming that she is completely oblivious to her husband’s behavior. Maybe she’s well aware and chooses not to do anything about it.

    1. The Not Mad But Occasionally Irritable Scientist*

      Or maybe she’s in that limbo zone where she knows, but the plausible deniability is what keeps the peace, and keeps her on his health insurance for the heart surgery.

      1. The Not Mad But Occasionally Irritable Scientist*

        Or maybe keeping the peace just lets them both live affluent, comfortable lives, living companionably together and pursuing their own interests and partners. Her being forced to confront what denial and comfort have plastered over could destroy her life. You just never know.

        1. Not So NewReader*

          Your first sentence: How many people in history can we name that have done this? Marriage is whatever two people agree to.

          I knew of a couple that married for companionship. Wife ended up more lonely than if she stayed on her own. That was because husband was dying and he would not tell her.

    2. Elizabeth H.*

      I agree. It’s entirely possible that she either knows, or suspects but doesn’t really want to know and hasn’t taken steps to discover it because of this. You don’t know the details of their marriage. As to the OP, you say they don’t have an open marriage because he lies to her and directs you to lie to her about his whereabouts etc. but you can’t really know what that proves. They could have a tacit understanding, they could have an open marriage in that he’s allowed to see other people but she is really adamant that she wants to be completely in the dark and able to pretend it’s not going on, etc. This might not be the most common of circumstances, but I think it’s a lot less unlikely than people might think.

      1. Yeah I'm Poly but I'm not a Sleazeball*

        This exactly. There are plenty of people that are in don’t ask/don’t tell relationships. There are lots of relationships that are not “typical” but work out fine for those people. Yes he is sleazy for misusing company money, and for making OP deal with his personal business, but other than that, there’s no telling. Personally I’d be finding another job before I went to a shady massage parlor for my boss.

    3. Gandalf the Nude*

      I actually wondered if her showing up for a surprise lunch might have been her trying to catch him out.

        1. ZTwo*

          OK, but if they are in an open relationship and she’s doing stuff like showing up at lunch as part of their sex life, that’s worse? Because the latter situation involves outside parties (the assistant) in their sex life and worse overall because if it’s tacit/complicit, than the OP’s boss is making the OP go through all this stress and effort for no reason? Because it’s fun for him and his wife? They got off on it? If both the husband and wife are theoretically fine with this situation then it’s truly evil to make the OP this involved, both because it’s wildly inappropriate generally and because it’s wholly unnecessary then.

          I get that there are “don’t ask, don’t tell” arrangements out there, but even if that’s the case this boss is wildly over the line and the advice is the same–the OP shouldn’t be involved and her boss is a jerk for making her be involved. If he wants tacitly accepted affairs he can arrange them on his own time and not literally bring them to work.

          1. Temperance*

            Eh arguably, the husband has violated all of this first by involving his assistant in his sex life. He has her booking hourly motel rooms, FFS, and it looks like his revolving door of mistresses visit him in the office for sex, too.

            1. ZTwo*

              Hmm, not sure if you meant to reply to me? I agree that the boss has been awful and violating of the assistant, regardless of what his actual relationship circumstances are. I was replying to the idea I saw in “But what about . . .” comments that this would be ok or reasonable if it was an open relationship.

              It’s not good or appropriate whether the relationship is closed or open, but if it is open he’s making the assistant do all this for virtually no reason (and feel personal/moral stress about it). That’s why it being open seems like a far worse situation to me, but in either case the boss needs to stop involving the OP ASAP.

              1. But what about . . .*

                My message in no way was meant to imply that the behavior is okay or reasonable, regardless of if the relationship is open. I was merely bringing up that the wife may know, since the comments had mostly been assuming the wife didn’t know. And actually I wasn’t even talking about it being open, but the wife knowing that he has affairs and choosing not to confront him, divorce him, what have you.

                1. But what about . . .*

                  And regarding the make him squirm comment, all I meant was that the surprise visit may not have been unplanned. Maybe she had suspicions and wanted to see how it played out – what would he do.

                  Regardless, I feel for the OP being in this situation.

    4. myswtghst*

      Agreed. It’s possible she knows but chooses not to acknowledge, it’s possible they have an arrangement where she just asks him to keep his extracurricular activities unknown to her, and it’s possible she just wouldn’t want to know. Add to that the risk of telling her leading right back to the OP (and possible retribution from the skeezebag boss), and I think it’s better to approach this from another angle. (Personally, I like the suggestions above about informing HR / the ethics line / the skeezebag’s boss of concerns about misuse of company resources.)

      1. Bwmn*

        Not to take this to be a political place – but among a number of wives, there is also an attitude of “boys will be boys” or “locker room behavior” – where certain things are fine provided they don’t have to encounter them. So things like cheating while out of town, massage parlors, whatever it is as long as I don’t know/am not embarrassed – etc. – while they never may have that conversation, there’s an understanding that these things happen and do not need to be discussed.

        I mean – if you look at any advice column, every 3-4 months, there is a letter where a woman is writing that she thinks a boyfriend/husband looking at porn is cheating. Not everyone thinks that is cheating, but there clearly is a group that is. After that things like getting a lap dance at a strip club, kissing, sexting, chat rooms, writing people on Craigslist – etc etc – what would or wouldn’t be cheating in a given relationship will have mileage. The OP’s boss is a complete sleeze and I think most/lots of people would consider him to be cheating, but on the flip side…..we’ also don’t truly know.

    5. Ann O'Nemity*

      Sure, it’s possible. There are a million flavors of open relationships. Maybe the wife chooses to remain in the dark. Sort of like, “You can have side action, but I don’t want to know anything about it at all. Do it on your own time and don’t let me catch a whiff of it. No calls to the house, no interfering with our time together, no charges on our joint accounts, etc.”

      The OP would have no idea what the couple’s arrangement is because they aren’t part of the marriage.

    6. Bonky*

      I’d actually be pretty surprised if she doesn’t know about at least some of it. The behaviour described here is so extreme that there’s just no way it’s not seeping outside his working life too. She could well have decided to deal with it in her own way; I’m sure she’s not very happy, but she may have decided to be as happy as she can be in a flawed relationship with a comfortable life rather than take the plunge into a new life. And jeez – heart disease on top of it all.

      You can’t see inside other people’s marriages. There’s a whole continuum for spouses in her situation: from open relationship, through grudging acceptance, to knowing but preferring not to know any details, to jacking it all in and leaving. Eric Schmidt (Google) has an “open” marriage, but his wife chooses not to have relationships outside the marriage while he does not. Again, I can’t imagine being happy in that situation, but…it takes all types.

      1. ouchie*

        “I’d actually be pretty surprised if she doesn’t know about at least some of it. The behaviour described here is so extreme that there’s just no way it’s not seeping outside his working life too.”

        Every time this comes up I have to chime in to say that, no, this is often not the case.

        I’ve done 100s of divorces. People always assume that the wife must know b/c the husband is being sloppy.

        We don’t know how good he is at covering it up to her. We don’t know how “separate” their lives are. We know nothing of her mental state.

        We have no way of judging one way or the other.

        “She must know” is a comforting fiction. It is a fiction.

        We have no idea one way or the other.

        1. Temperance*

          I have to say, it would be very easy for my husband to hide an affair, if he was so inclined. His workplace is roughly 1.5 hours from mine (opposite directions), he often works weird hours, and he likes to socialize after work with friends. He also pays the major bills, so I wouldn’t really know if he was paying for a mistress / manstress for drinks and dinner. He occasionally treats a friend, which is fine with me.

          2. BeautifulVoid*

            I hate to say it, but before having kids, if I were so inclined, I could have easily had an affair without my husband catching on, for the same reasons – erratic work schedule and handling most of the finances.

            Now I’m just too tired to even contemplate such a thing.

          3. K.*

            My best friend could easily have an affair. Her work requires frequent travel to the same city and she is the primary breadwinner and pays the big bills. She could carry on an affair in that city with basically no effort.

        3. Whiteybird the Rooster*

          Agreed, who can honestly say that the wife has some idea of what’s going on.

          What does bug me about situations like this is that she is being deprived of being able to choose to stay or go because she doesn’t have the information to make an informed choice.

          As a victim of infidelity myself, that’s the part that peeves me the most. He and his enabling friends/co-workers had information that I didn’t. It was a total surprise and shock when I accidentally found out. It had been going on for years, and the financial aspect of the deceit was hugely detrimental to my life and the implications are still being felt years later.

          1. Whiteybird the Rooster*

            Whoops, my comment was replying to Ouchie.

            I am certainly not in agreement with the idea that the wife must have some idea of what’s going on.

            The turd of a husband is putting not only her financial well-being at risk but is also exposing her to STD’s and who knows what else.

              1. Whiteybird the Rooster*

                He is sleeping with multiple partners including affair partners and sex workers. Who have had people that they have slept with/are sleeping with. He is exposing his wife to everything that those people could have.

                1. Zombii*

                  Agreed. That’s my main concern with telling/not telling. Unless he’s actively refusing to have unprotected sex with his wife, it is a risk—and there’s no way to know how much of a risk.

                  I hope the wife gets tested as part of her yearly exams, and isn’t just opting out because she’s married and doesn’t have to worry about these things anymore or any other slutshaming nonsense that keeps women from taking care of themselves.

    7. Hannah*

      I agree, that’s why I think the OP needs to mind her own business even though this is horrible. She doesn’t know for sure what the situation is, and maybe her getting involved would disrupt a situation they are both actually fine with. I think most likely the wife has no idea, and the boss is a scumbag who the OP should get away from as soon as possible. But it’s still not her place to interfere in the relationship in my opinion, even once she leaves.

  15. Bonky*

    Poor OP. Poor, poor wife. I also feel sorry for the mistresses; I’m sure it must be tough on them too.

    What everybody else has said: look for another job! Good admins are valuable. I don’t think I could look kindly on myself in the mirror if I was having to deal with this stuff on my boss’s behalf.

    I’d think twice about telling her: there’s a good chance she’s aware of at least some of it given how egregious the behaviour you know about is, and as Alison says, it may be that she’s someone who is better off *not* knowing. What a horrible position this horrible man has put you in. I hope you’re able to get out of there soon.

    1. Ehhhhh*

      Yea. I have to think that each mistress – if they know he’s married – think they’re the only mistress, and likely that he’s “leaving his wife as soon as she recovers from her illness”. So if they were to all become aware of each other… woahhh buddy.

      1. ouchie*

        We are also assuming they are mistresses and not professional sex workers. I’ve seen people conflate the two.

        We KNOW from OPs letter that he uses these services.

        My guess is that he has multiple mistresses and uses the services of sex workers. I doubt the mistresses are aware of either fact.

      2. anonymous*

        This. I know of a situation where a man was having multiple”flings,” but only one even suspected that she wasn’t the only one. There would have been Hades to pay.

  16. Hope*

    OP, you don’t want to get in trouble for being complicit in his misuse of company resources. I mean, hell, asking you to do these things for him on company/work time is already pretty dicey, since it’s not actually work related.

  17. Jane*

    Has he misused company funds or gotten reimbursement for third parties? If not, I guess that closes off one possible angle in the sense that if he’s paying for the other women to join him for lunch and upgrading his hotel suite etc. out of his own pocket, then its really not of interest to the company. Setting that aside, I definitely come down on the side of outing him, except that I think self-preservation has to come first, so if you’re worried about blowback on you (if he is likely to figure out you are the source) and this could affect your career going forward in terms of not having a recommendation from him, etc., as cold as it sounds, I think you do need to put yourself first over a stranger who is unfortunately being cheated on by her dirtbag husband.

  18. Panda Mom*

    Since the mistresses clearly know where he works and presumably know his real name, it is plausible that one of them could just as easily out him should they find out he is married (which may not be that difficult depending on ease of obtaining public records, what shows up in a Google search,etc). The wife deserves to know the truth. Once she has that information, she can choose whether or not to act on it. Like Violetta said, she is being put at risk for STDs and has no idea. That is very unfair to her and none of this is good for your conscience either. You shouldn’t have to be the gatekeeper to all of his misdeeds. Ugh.

    1. The Not Mad But Occasionally Irritable Scientist*

      No. It’s not OP’s business or her responsibility. The wife does deserve to know the truth. The boss does deserve to have all this blow up in his face. But it’s not OP’s place, and the wife may very well know – or not want to know. She’s going through a health crisis, and not knowing might be what keeps her on his health insurance while she recovers.

      1. Leatherwings*

        +1. We can all agree it would be better for the boss to be outed, but that doesn’t mean it’s a good idea for OP to do the outing.

        1. EddieSherbert*

          I think this sums everything up wonderfully – this guy sucks and he deserves to get outed… but it’s not OP’s place (or possibly in OP’s best interest as far as keeping a job / not being treated worse at her job).

          +1!!!

      2. CoffeeLover*

        I agree, it’s not your place. You’re not the first coworker to find out about another coworker’s infidelity. Is there a single office out there that hasn’t had some infidelity? At the end of the day though, you don’t mix business with pleasure. While your boss has completely forgotten this golden rule, I don’t think you should. There are people out there who would look worse on you for ousting your boss than they would on your boss for cheating*.

        As for the other stuff (i.e., paying for his “massages”, being asked to lie, etc.), I think Mike C said it best above, you have a lot of power to push back. Your boss has stupidly given you a goldmine of power against him. Of course, with great power comes great responsibility. Ultimately though, I think quitting for greener pastures would be the healthiest thing to do.

        *I’m one of these people. To me, a coworker telling another coworker’s wife he’s cheating would seriously cross a line with me. Thou shalt not get involved with coworkers personal lives. It’s not our business to place moral judgements on a coworker’s life choices (excluding obvious scenarios i.e., child abuse)…. even if that coworker throws those life choices in our face. While you may disagree with my view on this, I’m certainly not the only one who thinks this way. It would be akin to outing a coworker for being gay to his homophobic parents because you think being gay is wrong.

        1. Chalupa Batman*

          I have to agree (even though thinking about OP’s boss makes my skin crawl). OP knows company policies are being flouted, and that does concern them because they’re being made an accomplice. Stick to dealing with that. If the boss had kept his dalliances off the clock, in theory OP wouldn’t even know about them. OP should take the information about immoral-but-not-illegal activities as evidence that they shouldn’t trust Boss, but only take action on that part that impacts OP. Now, if OP’s refusal to protect Boss makes it harder for him to be a raging jerk, all the better, but for OP’s sanity and out of respect for the wife (I know it doesn’t feel like it, but plenty of pain has been caused by well intentioned meddlers), OP should stick to the issues that impact work and deal with those within work contexts, either by drawing a line with Boss or going above his head to make it stop.

        2. Anion*

          EXACTLY. I’m one of those people, too. I would have serious problems with a co-worker who did that. I learned a long time ago that when people do this sort of thing (telling on people, etc.) it is *never* for altruistic reasons. Never. It’s always a desire to stir up drama or see someone “punished” or get attention or whatever. There have been more than a few letters of this type here, and every single one that I’ve read proved this out.

          I was in a sort-of similar situation, or rather, I was admin asst to a boss having an affair, but it never occurred to me to tell his wife. I loved my boss. I knew his girlfriend–she came to the office all the time–and liked her a lot, and he got her daughter a job working right next to me (she was adorbs, I loved her). He’d been married a long time and with his girlfriend a long time and genuinely loved them both, I guess; I never asked, really, because it wasn’t my business aside from knowing that when Amy* was in his office with him and his wife called, he was in a meeting, and he always spoke extremely highly of his wife. (*Amy = not her real name, obvs.) He was an awesome guy, extremely successful, really interesting and fun and very discreet about the whole thing.

          My job was to assist him with whatever he was doing, NOT to judge it or him.

          He wasn’t my friend and neither was his wife. It wasn’t my place to get involved in his personal business or hers outside of work, and I had no idea what kind of arrangement or agreement or whatever they might have had.

          Not to mention–although this doesn’t affect my view that other people’s lives are NOYB–that my husband was married when we started dating. They were separated, basically (first he was sleeping in their spare room and then he moved out), but they were still married, and it still could have caused an enormous amount of problems for both of us if some busybody had decided to send his wife an “anonymous tip” that I’d come to visit him at work or whatever. Their separation and divorce were already contentious. She’d been physically abusive to him on more than one occasion (and I mean seriously; she was a tall, strong woman. Once she went after him with a knife). She would have been the same to me if she’d found out–she did suspect me at one point before we even started dating, and her response to that was to spread rumors about me being an STD-ridden drunk. The destruction and misery that “outing” us would have caused would have been immense, frankly, and it would have served absolutely no purpose except to “punish” him for finally finding a way out of a disastrous marriage. What a victory that would have been for the “outer!”

          We’ve been together almost twenty years now and married for almost seventeen, and no, I have never suspected him of cheating and know he never would.

          The OP’s boss’s relationships are none of the OP’s business beyond what she’s asked to do as part of her job (which includes handling his calls and appointments, making his reservations, and sorting his expense reports etc., sorry). Just because her boss is dishonorable doesn’t mean she has to be.

      3. Panda Mom*

        Nowhere in my post did I state that it was the OP’s responsibility to do the outing. I said the mistresses could just as easily be the ones who made the reveal. None of this is fair to the OP but I will disagree that it’s not her business. The first time you see or hear something, it’s not your business. Once you have become complicit in the coverup, it has becomes your business. It now affects her job, her well-being and her credibility if problems develop higher up the chair and it is discovered that she was playing a role in this mess all along.

        1. Leatherwings*

          I think it’s a huge huge stretch to say OP has become “complicit in the coverup.” That implies that OP has willingly covered for the boss. This just isn’t like a friend discovering and covering for a cheater, it’s a work situation where OP has felt that she has to do perform these actions or risk her relationship with her *boss* and her job. There’s a power dynamic here I don’t think you’re taking into account in the language you’re using.

          1. Panda Mom*

            I was not just referring to the personal aspects, I was referring to actions taking place in the business in terms of financials, credit card mixups, etc. English is not my native tongue I must apologize if you are reading something from my choice of words that is not intended.

      4. Property Manager*

        OH, good point about the health insurance. I mean, yes, he’s a sleezeball, we all seem to agree. But marriages are complicated.

        OP — I worked for this guy once in my life, also (a little different, though, because he was the owner of the company). Anyhow, all the employees new about the affairs — the girlfriends were the ones who came with him to company events. But we also all knew his really sweet wife and daughter. Anyhow, we all kept our mouths shut and years later the wife finally asked for a divorce so she could get re-married. She really knew ALL ALONG and just pretended not to just to put on a happy image for people. She knew, but she accepted it as a trade off for financial security, health insurance and a big house on the hill. She didn’t like it and finally, enough was enough. I don’t know what would have happened if someone tried to out him. It probably would have been really awkward.

        Anyhow, I guess my point is that she’s married to him, so she probably already knows he’s a jerk.

  19. Biff*

    Geez, we didn’t even make it a MONTH without a contender for Worst Boss of the Year.

    OP — I am so, so, so sorry. This is some screwed up “Mad Men” wannabe crap. I’m beyond sorry for you.

  20. Jean*

    I’m not going to lie for my boss. I’m not that good at lying anyway, and I know that I would get my stories mixed up and end up with everyone pissed off at me. I wouldn’t tell the wife though. I don’t like to get involved in other people’s marriages.

    1. The Not Mad But Occasionally Irritable Scientist*

      This would be a fun thing to tell the boss. “I’m a terrible liar, so if you ask me to cover for you, I might just get my stories all messed up. Wouldn’t that be terrible for you.

      1. SophieChotek*

        I agree…I’m a terrible liar too…but it sounds like the OP has lied often enough in the past that this reason might not work now. How did the OP suddenly become a terrible liar?

        2. Countess Boochie Flagrante*

          It could be more of “it’s getting really hard for me to keep these stories straight!”

    2. The Not Mad But Occasionally Irritable Scientist*

      This would be a fun thing to tell the boss. “I’m a terrible liar, so if you ask me to cover for you, I might just get my stories all messed up. Wouldn’t that be terrible for you.”

  21. K.*

    I would not tell her. For one, you don’t know how she’ll respond – I’ve known women who lash out at the person who told them about their cheating SOs and refuse to believe them, cutting off the person who told. She may well be a person who would rather not know; people have different lines in the sand when it comes to infidelity. Second, even if you tell her anonymously, the odds of her figuring it out are high – you know and manage his schedule, which the wife presumably knows. Third, telling the wife may change nothing (again, she may be content to go along with the behavior and he doesn’t seem inclined to stop anyway), or it might blow things up and lead to a messy divorce, complete with paternity scandal, which you’ll have to deal with because your boss is on the record as being someone who smears his personal life all over the office. Telling her while you work for him is only going to make things more difficult for you.

    If you MUST tell her, I would do so only once you no longer work for him. For now, I would tell him you’re not going to be complicit in this anymore, I would get HR to get your back on that (he’s misusing company funds, at the very least, and I wonder if sending you to a massage parlor could be construed as sexual harassment) and I would start looking for another job immediately.

    1. Lison*

      I once worked with a woman who one day was telling me how she cut her best friend since she was 4 because the friend told her when she was away her fiance was always seen with another woman and they both slept in the same house (either hers or the house coworker shared with him) and provided a list of people who would confirm these facts (really small village and my coworker was renting where we worked during the week and only back at weekends). Coworker was indignant that this ‘lie’ was being told and “she just wants me to embarrass me by getting me to ask people so of course I won’t. He would never do something like that”. So yep people can go far out of their way to avoid believing things and if someone will retaliate against a best friend of 25 years an administrator has no chance if the cheated on person takes this attitude.

      1. Lissa*

        Ugh, that’s so sad. Poor friend. I suppose it’s easier to believe that a trusted friend would, for no reason, engage in a campaign of humiliation and lies and make up this story than it is to believe your husband is cheating, but … yikes.

  23. Construction Safety*

    Well, the OP could always say that the visiting trollops are vendors, which is technically true.

    1. Emilia Bedelia*

      That’s a pretty unfair thing to say about women who may or may not know that he’s married.

      Either way, he’s the one in the wrong here. He’s the one having extramarital affairs.

      3. Pebbles*

        Yes, the boss is definitely in the wrong here, but whether the women know or not…in his office? Really? I would never imagine meeting my husband at work for a tryst in an office. Didn’t we have a duck club letter where it was a pretty universal sentiment that sex should stay out of the office (and cars in the parking lot) no matter what? And if someone I was dating (back when I was single) could only meet for sex in hotel rooms and his office I would like to think I’m smart enough to pick up on a feeling that something is not right here.

        There’s some big red flags for the ladies to pick up on if they don’t know, and if they do, then they don’t care about the wife at all, which I consider to be morally reprehensible. (Again, not arguing that the husband is in the clear here, because NOPE.)

        1. Temperance*

          I worked in shared office space, and can confirm that people have sex at work and watch porn at work much more than you would want or expect. I would also consider it a red flag if a dude only wanted to meet up at hourly motels or his office, but not everyone thinks like we do.

        2. Emilia Bedelia*

          But, who cares? We can speculate all we want about what the particulars of the situation are, but the fact is, the moral character of the other women is completely irrelevant to what the OP should do in this situation. Getting into the discussion of “but who is really the most wrongest?” here confuse the situation.
          Snarky comments like the original one in this thread don’t help the OP and they add nothing to the discussion

          1. Fortitude Jones*

            THANK YOU. These other women have nothing to do with the OP’s boss sucking royally as an employer.

          2. Pebbles*

            I actually would find Construction Safety’s comment useful because were I the OP, I could see myself using just this phrasing to the wife should she pop in the office for an unexpected lunch again. Reading past the snark, the message is to STAY OUT OF IT, which I wholeheartedly support. If I were the OP, I would be brushing up on my resume, actively job searching, and going to HR, because there’s no way I’d be able to keep up this farce. I would even go so far as to quit without having something lined up if my husband and I determined our finances could handle it (not suggesting the OP do this, BTW).

            You’re right, the character of those women is irrelevant to what the OP should do. But I disagree that the overall comment adds nothing, and if I’m understanding the conversation here everyone is objecting to a single word the commenter threw in which seems like nitpicking to me and is now being attacked for.

            1. Emac*

              Not to derail, but objecting to that one word isn’t just nitpicking – it’s objecting to the way that the “other” woman typically gets blamed for being a homewrecker, while the man is given a lighter accusation.

              And actually, I object to the word “vendor” as well since it implies that the women he’s having affairs with are ‘selling’ sex in exchange for something.

              1. Ask a Manager* Post author

                Yes — there’s a “women can’t possibly enjoy sex for sex’s sake” vibe to it, even though the man is clearly doing exactly that himself.

                1. Pebbles*

                  I guess it’s just me then, since I don’t get that vibe from the comment at all. I’ll drop this now and stop derailing the thread.

              2. Anion*

                Plenty of people in these comments are implying that these other women must be riddled with STDs, which I also find offensive.

    3. ouchie*

      While I am not a fan of absolving knowing mistresses from all responsibilities because “he took a vow” you are being very harsh and very misogynist.

      You have no idea what he has said to these women. You have know idea what the situation actually is.

      If they don’t know he’s married or do know but think he has a hall pass, the situation is very different from if they knowingly participate in cheating.

      Even if they are knowing, willing participants, who either want to hurt the wife or don’t care and thus have some moral culpability they do not deserve the word “trollop.”

      This is really, truly a vile thing to say.

      1. soanonforthis*

        Also, you really can’t help who you fall in love with. It’s very hard to walk away from that, even if they know he’s married, and they might already feel terrible about themselves. I was involved with someone who, while not married, didn’t treat me well, and I couldn’t let go, and my therapist literally compared it to a heroin addiction – you know it is bad but you still go back because you can’t help it.

      2. mcr-red*

        Having been cheated on by my ex and his knowing and willing participant who had met me and our kids and been to our house many times… I can come up ALOT more vile words to call both my ex and his buddy than “trollop.” #sorrynotsorry

        1. JB (not in Houston)*

          We can all come up with all kinds of words to describe people who have wronged us, and though harsh those words can still be accurate and fair. You’re in the best place than us to know if the adjectives you’d want to use in your case are accurate. But it’s not fair or ok to use misogynistic words like “trollop,” and here when we don’t have nearly enough information to draw the kinds of conclusions you seem to be drawing.

  24. whichsister*

    Is this our first Contender for Worst Boss of the year? Sending her to a massage parlor to fix his tab?

  25. Christine*

    Do not tell the wife. Since she’s in the middle of a health crisis, the stressor is not needed. She could be aware, but ignoring it considering her health. I would be so tempted to have friend block their phone number, call and pretend that they are calling from the health department and/or a doctor’s office and that he’s been exposed to an STD.

    I highly recommend going to HR, and tell them what he’s doing, but document everything, including your time running his errands. Or his boss.

    Also keep a record outside the office incase you do get terminated as retaliation so that you can file an appeal. You can also use the threat of telling his wife if he threatens termination.

    I’ve worked as an administrative assistant for years, and it seems that bosses are having more issues with personal boundaries than ever these last few years. My boss wants the work studies to take her to doctor appointments, told her that they were not allowed to drive as part of their duties because of liability issues. Or me to pick up things or her when I’m in town. I nipped that in the bud, I work in town, but live in the county … I do not go into town for anything except on the way home. I just went to HR, she’s been told in the past that admin assistants are not personal assistants. Always pushing the boundaries.

    Than OP is dealing with this slime ball. Hey Managers out here —- administrative assistants are not your private errand girls, etc. It’s one thing to ask me to pick up lunch for you by walking the next block over or drop your mail off when I go to the post office. I’m not picking up your prescriptions, or going to the dry cleaners for you.
    ” OUR Mutual employer is paying us both to work for them.”

    1. The Bimmer Guy*

      I agree with not telling the wife. If I were in her position, I think I’d want to know, but, like Alison said, you never know how someone will react and how it may hurt them…and if your intentions are pure and you’re not just trying to be conniving and create trouble, that should very much be a factor.

    2. V*

      On your last point – this varies widely by office. I work at a law firm where attorneys bill their time to clients but assistants do not. If an attorney spends an hour on a personal matter, that hour can’t be billed; if the assistant can take care of it instead, allowing the attorney to work during that time, the company comes out far ahead, even if it ends up costing overtime pay for the assistant. So while there may be tasks that are too personal to be appropriate to ask an assistant to handle (baby sitting a sick kid, as an extreme example) there are many that are appropriate (e.g. booking flights and hotels for a personal trip). One attorney at my office routinely has his assistant do his Christmas shopping on company time. He also bills more time than anyone else in firm and regularly works on weekends. The office is more than happy to have his assistant go out and do his shopping during the workday so that he can keep working and billing. And she likes having a couple of days out of the office as a change of pace. Mall holiday craziness is a lot easier to handle when you are paid to be there. It all depends on the office culture (and of course companies should be up front about this when hiring so those who do not want to these kinds of errands can self select out.)

      1. Christine*

        V, I agree with you 100%. I work for the state and they have strict deadlines about it
        My supervisor is over a small department of 20 in the corporate world she would be considered a low level manager. If she was the VP of academic affairs it would be different. But you are not supposed to use work studies for personal errands or ask them to use personal vehicles for work related errands either.

        I had one job I got as a temp and they tried to get me run personnel errands years ago, the contract they signed stated that we could not use our personal vehicles for their business. It’s a liability issue. and the agency I worked for didn’t want to supply that type of coverage.

  26. PK*

    Nope. No way I’m getting involved in that one. I make it a point to stay out of other folks’ relationships.

    You can stand up and say you’d rather not do any more lying or covering for his personal affairs outside of work though but IF he is hiding it, you may find yourself without a job if he thinks you are going to tell his wife. There’s just not many ‘win’ decisions here.

  27. The Bimmer Guy*

    What a thoroughly-despicable person. I wonder if the LW would have some legal protections if she refused to do this, and was fired as a result.

    1. fposte*

      Since what she’s being asked to do isn’t illegal, the only exception to at-will I could see coming close to fitting is the covenant of good faith, and that’s only in eleven states; my impression is that’s also a pretty high bar to meet.

      And of course it’s not a protection once a firing has happened; it’s about getting compensation for that firing, and I suspect this one wouldn’t be likely to win enough for a lawyer to take it on.

      1. Sue Wilson*

        Pretty sure “massage parlors” of a certain sort are illegal, and OP’s the one who went and paid for it.

        1. fposte*

          Hmm, that’s a point. Though of course it’s still true that the correction isn’t going to be much help.

        2. Hmmm*

          Well, I might have gotten the wrong takeaway from that but I got the impression that the boss had put the massage parlor tab on his company card, and what he wanted the OP to do was go back, ask them to refund the money to the card and accept cash instead.

          So there is still a record of that transaction happening in the boss’s name, whereas the cash transaction isn’t tied to the OP’s legal identity in any way.

  28. Ehhhhh*

    So when I was in high school (drama drama, but relevant here) I anonymously tipped off an acquaintance that I knew, that her boyfriend was cheating on her – regularly. I knew this to be a fact because the boyfriend was very good friends with my ex boyfriend and I found out that they did these things together and covered for each other.
    Anyway, obviously it was found out that it was me and it was… horrible. Acquaintance told BF and of course believed BF hands down, and she and BF went out of their way to “ruin my life” as only juniors in high school can. I was a pariah for the last two years of high school. It sucked. All because I tried to do the right thing (I didn’t know her well enough to tell her directly, so I did it anonymously).

    I grew up and went to college and am no longer a pariah in case you were wondering, but I hated high school as a result of this incident.

  29. HR U of Me*

    Keep this on the work side of things. If you are with a public employer, or within a publicly-traded, or big-enough company, most seasoned HR folks know all about this and are the ones to address this as the threat to operations that this is. (Notice that I left the personal relationship element out of it) This is happening on-site, and he is using company resources to support it.

    If this is a super-tiny business operation, check in with a reputable headhunter, as stellar, professional admins are worth their weight in gold, and get your career kite hitched to more favorable winds. Higher ed is always looking for quality admins AND you can negotiate tuition remission to get over to the other side of being the change in leadership that you want to see in the world. Just floating a balloon, and am not even pretending to know all the facts.

    1. HR U of Me*

      This is…let HR, your EEO/Sexual Harassment Office (Hostile Work Environment), or Corporate Counsel be the heavy. First go to a solid HR professional and report about settling the bill for the massage place – that he called a strip club – and ask if this is in your job description. ESPECIALLY if you have a ton of other work to do.

      You are not the heavy. He is way out of line. If you don’t have this sort of backing, know that there are awesome bosses out there (that have a better stripe of humanity) that are looking for good admins. You will find them.

      1. Emmie*

        OP: Please also tell them about the do not disturb office visits with the locked door. My mind is going to intimate activity. Having this happen on company grounds is risky for the company, and a seasoned HR professional or corporate counsel will recognize this. It’s also better to be transparent about the whole situation b/c it will show the breadth and insanity of the risk. FWIW, I am SO sorry you’re dealing with this OP. I applaud the compassion you have for his wife. Good luck.

  30. MuseumChick*

    Ugh. I’m so torn on this one. Your boss is such a little worm. If the wife wasn’t going through a health crisis (and since you say you can tip her off anonymously) I would say do it. But I am someone who would want to know, as Alison said, there are people who would prefer not to. Given she has going through a serious medical condition I would not tell her (right now).

    What I would probably do is wait until she is healthy again (and possible right before I left the company for a new job) and then anonymously out him. But that’s just me.

    Does your company have an HR department you can speak with?

  31. boop the first*

    I am also terrible at lying. It’s one thing to be a witness to this, and quite another to cover for it at the expense of your own professional and personal integrity. If you’re gonna go full participant like this, you might as well get some financial bonus out of it.

    I get that complete financial LOSS is at risk here, and I don’t know what kind of reference you’d get from someone who thinks nothing of women (assuming you are one? 50% chance here). I just wonder if your company would be so chill about this man clearly not doing any work while all of this is happening.

  32. Stephanie*

    OP, I’m sorry you’re dealing with this. I would be sending out resumes like mad. I don’t think you should tell the wife. It’s bad enough your boss wants you to cover for him, you don’t want to get involved in personal drama as well. The wife may turn a blind eye to it or have some tacit understanding or accept it as a downside to an otherwise favorable situation or just double down (“Fergus would never cheat! He’s a good man! You’re a horrible person for saying that!”).

    If you feel comfortable, go to HR or an ethics hotline and report him. I don’t believe lines like that at work are truly anonymous, so be prepared for some blowback.

  33. Critter*

    Wow. This is completely awful.

    I would not tell the wife, especially not anonymously, because it would be quite obvious that it was you, and because it’s not your responsibility. Anyone would understand how this guy is abusing his power over you; I don’t think you have an obligation here.

    I’d flatly refuse to do anything that involves you in this awfulness. It’s not work; you’re helping him manage your personal life. If it’s the sort of admin job where that is expected, then I’d start looking, but still refuse to be involved.

    Then again, this is what I’d do; I’m really sorry you have to deal with this.

      1. Christine*

        I wonder about managers that need assistance managing their personnel life. If they have such an issue managing their personnel life & they expect their admin assistants to make up the slack per say; I wonder about their ability to manage anything at work

        If he’s misusing her time, he’s misusing funds. If she’s helping him fudge expense reports, she could be fired as a result of not reporting it.

  34. Purple Jello*

    OP – Does your company have an Ethics policy? Seems to me your boss by asking you to lie for him is requiring you be unethical as part of your job.

    1. HR U of Me*

      Ethics AND Audit folks would be interested, if the infrastructure is there. I’ve had my sister stay with me during conferences because I have the space, so the travel is actually less dicey work-wise unless he’s billing beyond personal meals. If either person is in the industry, it’s even tougher to challenge a comped meal.

      The real point is we have been so conditioned to believe that the protective systems will not work for the whistleblower. We must INSIST that they work for the greater good, and not pillory the person who says – this needs to be reviewed. A presumption of good faith is in order.

  35. RVA Cat*

    Speaking of the risk of STIs here, I’m thinking that not only should the OP go to HR/ethics line for the misappropriation issue, but someone needs to make sure whoever cleans that office is following universal precautions (gloves etc.) for exposure to bodily fluids.

    1. Ann O'Nemity*

      Yes, I wouldn’t be comfortable sitting on or touching any surface in boss’s office. Seriously.

    2. Jamie*

      If that’s the case, then they should be taking the same precautions cleaning every office because sex happens even with people who know how to keep it quiet.

      (Not in my office. Just want to be clear that unless a possum and raccoon are using it for secluded rendezvous’ to revel in their forbidden love then it’s safe to clean my office without bio-hazard protocols in place.)

      And I’m in camp don’t tell the wife, but deal with it as a work issue if possible because being asked to pay off a massage parlor and buy jewelry is probably not the work product the company as a whole is expecting from the OP. Unless he owns the company or tptb are complicit in which case – I’d be brushing up my resume.

        1. Jamie*

          Awww. Elbows deep in major implementation atm but weird office sex will almost always draw me out.

          Reading about it. Here. To clarify.

          Btw I was talking with someone irl about a job they are interviewing for and was able to work in, “You are not in a brothel line-up. You’re in a two-way business discussion.” organically.

          It’s my mission to make that phrase of yours mainstream.

          1. fposte*

            I will do the same for you with a sentence involving the phrases “elbows deep” and “weird office sex.”

  36. Jady*

    Please out this slimebag to his wife. I would want to know. I think most people would want to know. Who-knows what else this man has been doing for who-knows how many years.

    But along with this, still start looking for a new job. Because:
    1 – If outed, the man might assume or figure out it’s you, and you’d probably get fired.
    2 – Refusing to be his slimebag-sidekick will probably get you fired. 100% talk to HR or someone higher up beforehand. But even with HR’s backing, that doesn’t mean he won’t find a way.
    3 – He’s going to keep doing this regardless of what happens with you or his wife. He’s not only lying to his wife, but to all the other women as well.
    4 – Him using company funds or company paid events puts you in a position of helping him do things that would probably get both of you fired.

    If you have the opportunity, I’d out him to all the women you know about. Just think about being in any of their shoes. Would you want to know??

  37. Anon Here*

    I just want to put out there that are some people who would NOT want to know and I count myself among them, at least for in many circumstances, including potentially the wife’s circumstance here. It is possible the boss is a slimeball, but it is possible that he is kind and caring with his wife and doing his best to take care of her while she is sick. Perhaps they can’t have the physical relationship they would like because of her illness, so he seeks that out from other people. He knows it would be embarrassing or upsetting or otherwise difficult for her if he was cavalier about it, so he maintains these relationships discreetly so as not to hurt her. If those were the circumstances I were in, I wouldn’t want to know. I understand that I am in the minority here, but I am not alone.

    1. MuseumChick*

      I think the information we have from the OP points to a very non-discreet cheater. Having his mistresses show up to the office, spending long periods of time with them behind closed doors (on company time), having a child with one of them, sending the flowers and gifts to the mistress but not his wife etc. Assuming all of this is true, he is most likely just a slim ball getting away with whatever he can.

      I’ve read some article online about people who seek sexual gratification outside their primary relationship due to a partners health. They are consistently much more discreet then the behavior described here and certainly don’t involve getting the other person pregnant/getting pregnant by the other person.

  38. Beancounter Eric*

    Your boss is a reprehensible bastard who frankly, deserves to be fed slowly through a wood chipper feet-first. First for cheating on his wife, and second for dragging you into the mess covering for him. You, however, need to take a hard look at your personal ethics for being complicit in covering for your boss.

    You need to have a chat with HR, and come absolutely clean about boss’ actions, and frankly, your role in the cover-up. Depending on the company, you may find yourself unemployed for falsifying expense reports on his behalf.

    Clear your conscience, go to HR, and tell the tale.

    The wife should know – she may already know, and accept the situation. As to the issue of alerting her, much depends on your relationship with the wife.

    1. Helen*

      I don’t think OP has falsified any expense reports. There is nothing in the letter to indicate that.

      1. Beancounter Eric*

        “He also submits expenses from his business trips (where he has traveled alone) and I have to re-calculate everything because he has upgraded the company-provided hotel room to a better one on his personal credit card and bought breakfast for more than one person the next morning. When this happens, he tells me he had “company.” There was also an incident where he came to work panicked because he said he accidentally used his company credit card at a strip club. He sent me to retrieve it and pay his tab with cash, but the address he sent me to was actually a massage parlor.”

        I have spent years reviewing expense reports, and if we found out someone was gaming the system as above, we’d be taking their expense reports apart and doing a very detailed review. I was never asked to look the other way…but I would like to believe that had I, my response would be “this goes to the audit committee – don’t like it, you can hire my replacement. Do it today…..because I will not be here tomorrow.”

        1. Accountant here*

          The credit card at the strip club is problematic, but I’ve been an account for over 20 years and I’ve dealt with company credit cards and expenses for 15 years. It’s never been a problem at any of the companies I worked with for someone to upgrade their company provided hotel room or other things (airline tickets, meals etc) and pay the difference out of their own pocket. It happens often, at least where I have worked. Since OP says she is recalculating to reflect her boss paying the upgrade I don’t see why it would be a problem.

          1. Beancounter Eric*

            My interpretation of OP’s remarks is that the adjustments are hidden. In my 25+ years of accounting experience and in every company I have worked for, finagling expense reports to conceal ANYTHING was considered improper.

        2. Jamie*

          I agree with the massage parlor issue, but the other stuff isn’t gaming the system, imo. If I was travelling for work and wanted to take one of my kids, or a friend I’d use my own card and submit only my allowed expenditures for my travel – there is nothing shady about this from an accounting perspective ime.

          Even the massage parlor thing – which….ewww…but if you inadvertently used a company card and realized it correcting it by making proper payment to rectify also the correct thing to do.

          I did that at a toll once…notices my Ipass was missing once I got there and line of cars honking behind me I pulled out the company card instead of mine by accident. Realized it when I got home and emailed accounting and dropped off the $3 to them the next day. Had it been a larger sum and a place I’d have been able to change the payment, I would have.

          But what’s missing here is the OP paying in cash didn’t remove it from his credit statement. It would just show the charge and then the voided charge…so it kept it from being a financial issue but accounting still would have seen the charge.

        3. Jessie the First (or second)*

          I read that entirely differently – he is entitled to be reimbursed for certain expenses when he uses his personal card. So he used it, but used it for more than he is entitled to – such as breakfast for 2 instead of for 1. He is still entitled for reimbursement for breakfast for 1, so OP has to figure out what that expense actually was. He’s not suddenly unable to be reimbursed for a business expense simply because he spent more.

          It’s not gaming the system. He’s having her submit the business portion of expenses for reimbursements, and leaving the person portion of the business expenses for himself. That’s… what he should do.

          He’s a sleaze, but that part of it reads as normal (again, aside from the ick factor).

          1. Jamie*

            Exactly. If you take out the “who” for the company and the “what” for the massage parlor charge there is nothing shady here.

  39. Karanda Baywood*

    I’m surprised at so many commenters saying “Out him to the mistresses.” What makes you think they don’t already know?

      1. K.*

        They might, but I’ve known more than one woman who only found out her boyfriend was married AFTER the relationship ended. I think it’s just as likely that they don’t know they’re mistresses as it is that they’re willing “other women,” and I would bet in either case, they don’t know that there’s more than one “other woman.”

    2. Jady*

      If they already know, no harm done then.

      If they don’t already know, and don’t care – no harm done then.

      If they don’t already know, and do care – you could save them from a lot of trouble, misery, STDs, embarrassment, (and for the others that don’t have kids like one of them do! being a single parent!)

  40. Katie P*

    My immediate question is how important is your job to you? Are you looking to change jobs anytime soon? And how much is this weighing on your conscience?
    I know for me I would be overrun with thoughts on how to let all three women know.

    1. Jamie*

      Right?! Anyone else really need a shower right about now?

      I know of someone who found out her husband had another family on the side when his youngest child from his mistress was almost 30. My only question was how did she not miss the money being used to support another household for decades? But that may be because I’m lacking a soul.

      1. Temperance*

        I grew up with two kids who were a second family. It was such a farce. Everyone knew who their dad was, their mom openly referred to him as her “boyfriend”, and his wife supposedly had no clue. It was a true shitshow. s far as I know, their dad supported them financially, and was involved.

        1. Jamie*

          Similar situation. It was as if he just had a second wife and kids – idk if the kids believed their parents were married or not but definitely a couple for 30 years.

          I can’t even wrap my head around that level of deception. And it sounds like an absolutely exhausting way to live.

          1. Temperance*

            It was sort of weird, the kids knew that their dad had a wife and that they shouldn’t meet her, or her kids. It’s very strange, but it seemed to work … for at least 25 years. lol

            1. zora*

              gah, just the thought of these situations makes my skin crawl…. And how is the boss in the letter pulling this off in this day and age? This stuff seems so 1950s to me… {{{shudder}}}

              1. Temperance*

                I’m 33, and the “kids” are now 32 and 33. So it’s apparently never ending. Gross people going to keep on grossing, I guess.

            2. Natalie*

              Well, split and recombined families aren’t unusual, so it’s not unheard of that your dad might have a wife for normal, non-secret reason. And (speaking from experience) kids are born blank slates as far as the topic of how a family should work. By the time they understand that they are in a non-normative family, they’re so acclimated to it that it doesn’t seem strange at all.

  42. Mini Snowder*

    I don’t know if this has been suggested anywhere above, but what if OP sent something anonymous to his wife? Maybe on the way out? I do think it is probably safest to leave the role. It sounds toxic and awful.

  43. Cochrane*

    Ethics aside, this guy had better be taking care of the OP financially in exchange for their assistance in keeping all these plates spinning in his oh-so-complicated private life.

    While I would advise to make an exit to a new job ASAP, the thought of outing him would cross my mind if he expected a mob consigliere level of service but paid me chump change.

      1. Cochrane*

        Not a shakedown in exchange for silence, but the fundamental question of “am I getting paid enough for this crap?” that pretty much every working person has asked themselves at some point in their careers.

        If SleezeBoss acknowledges these services that OP is providing above and beyond the admin role with a nice bonus or some other perk, that would make it a little more tolerable than if he expects them the bury his bodies without any extra consideration. Being a slime is one thing; being a cheap slime is even worse.

        That said, OP is in a no-win situation if they stay. Get out while you can.

  44. LawCat*

    OP, can you afford to be unemployed?

    If no, keep your head down and focus your energies on finding another job.

    If yes, I’d follow Alison’s advice,

    It’s a completely crap situation to be in and I’m sorry.

    1. Manager Shmanager*

      I completely agree with this. It’s past time to job hunt.

      Based on your letter, describing all of the work you have done to support this guy, you seem like an exemplary admin that any organization would be lucky to have. Imagine a job where you can use your talents to help a leader you respect!

  45. MWKate*

    This is a tough one, OP. I think I would find it similarly hard to determine what to do. It’s true that you are under no obligation to tell his wife – but I can understand seeing something you know is wrong happening and feeling terrible helping to conceal it.

    What makes this even worse – is that he (presumably) has a child with one of these women. Whatever nonsense your boss is getting into, this poor kid is going to be the one to suffer. The baby doesn’t deserve to grow up as a hidden shame child. Not that this changes your responsibility – but I think is increases the chance that this is going to come out on it’s own at some point.

    I would go to HR if you can, look into the suggestions about whether or not you could be deemed complicit in possible illegal activities, and then decide for yourself which option you can personally deal with having chosen.

    1. Christine*

      The OP could send the wrong flowers, note to the wrong women etc. If she messes that up enough, he might not ask her to do it again. Just a thought. I would be job searching and notify HR.

      Since he is overstepping the boundaries so much, I doubt he’ll be accept OP’s declining to continue providing the service.

  46. One Handed Typist*

    I do not think it is your place to say anything to the wife. You are not a personal friend. You aren’t family. You are connected to this man via business. Your interests are in business matters. More than that, I think it is extremely likely that your boss would tell his wife that you are sour grapes because he shot you down. Then he would make it a point to remove you from your job.

    You should escalate this above your boss. There is absolutely no way you should be spending company time fishing out receipts and charges to strip clubs or massage parlors or going to jewelry stores to make pickups unless the store is donating to a work event. That’s misuse of company time and funds and the longer you let this go on, the more responsibility you are choosing to take on yourself.

    Document everything. Dates and times that you made pickups at stores or ran errands out of the office. The dates and times of visits for women he went on to have sex with in his office. That’s a huge deal – what if his boss needed to talk to him while your boss had a “visitor”? I’m concerned that you saying nothing about this fraud and misuse of resources will open yourself up to being an accessory and will cost you your job as well. You need to bring this to HR and your boss’ boss.

    1. CanCan*

      Absolutely!!!

      If there is an HR department, or a boss above your boss, talk to them. Give them specifics: what you observed, what your boss asked you to do, – specifically where it involves company resources (time, money, office space, your time). Make a point that you do not wish to interfere in the boss’s personal life, but that you are concerned about misappropriation of company funds, inappropriate use of staff time (re. sending you to pick up jewellery or pay for body rubs) and inappropriate activities in the office. You can also mention that you are uncomfortable lying to the wife, and ask if it would be Ok for you to simply say that the boss is “unavailable” without providing any further detail.

      If there is no one above your boss, keep your head down and look for a job. It doesn’t sound like there’s anything you could tell him that could change things.

      But definetly do not tell the wife. It doesn’t matter whether it will be good for her to know. It may or it may not. Your career is not worth that. Even if you decide to tell after you’ve found a new job, give it some time: the new job may not be all you wanted, and you may need a reference from the Cheater to look for the job after. If you tell the wife, anonymously or not, the Cheater may well find out it was you.

  47. Venus Supreme*

    WHAAAAAAAAAAAAAAAAAAAAT

    This situation is so ridiculous. As someone who has been cheated on, I’m sick to my stomach reading this. OP, I do not envy you. This is truly a crappy situation to be a part of. If it’s at all possible, I’d start job searching ASAP. In the meantime, contact your boss’s boss or HR to try to get yourself out of this tangled web. Your sleazy boss especially needs to keep his financials in order. That’s a big deal.

    Personally, if it were me, I’d want someone to tell me if my partner’s cheating on me. (I’m also good friends with the person my ex cheated on me with, so I might be an outlier). But I am not this guy’s wife and there are too many snags in this situation that you cannot simply tell her what’s going on (anonymously or not) and not expect it to turn around on you. I think it’s in your best interest to be as hands-off as possible. My biggest fear for you is anonymously telling the wife what you know, her confronting Boss, him going back to you because “you’re the only one who could possibly know this,” and the wife retaliating by telling any higher-ups and you’re now roped into this whole mess. With the way he’s been handling his credit cards and having you go to in person to rectify the problems and such, there could be legal issues. Not good.

    PLEASE PLEASE keep us updated, and soon!!

      1. MWKate*

        Right! To me that says this is all coming out at some point anyway. Mom’s going to figure out he’s not leaving his wife, or that there are multiple mistresses, and presumably sue for some kind of child support or paternity test.

        Poor wife. poor kid.

        1. Venus Supreme*

          Yeah, you would think that when the mistress told him she was pregnant he’d have a reality check and try to sort out this mess. Apparently not. In addition to the wife, I really feel for the mistress and her child.

          And it’s not OP’s responsibility to do what he’s unable to.

        2. Rater Z*

          This reminds me of when I was doing tax returns about ten years ago. The young couple, about age 25, had a weird story.

          The guy told me (in front of his wife) that when he was in school, he had a one night stand with a young lady and she got pregnant as a result. She never never told him about the child and he got married, not knowing he was a father. His wife didn’t know anything about this, including the one night stand. I asked him if there was a paternity test. Yes, it came back positive.

          When the child was about four years old, she filed for welfare. The obvious question they asked was “Who is the father?” She told them. That left him with problems, both huge. First, he is five years behind on child support with all of the attached problems — possible jail, loss of drivers license, probably owing at least ten grand in support, etc. Second, telling his wife about what had happened. I made the comment to her that something like this can blow a marriage right out of the water and she said it almost did.

          He seemed like a nice kid who wasn’t a sleezebag. He just did something that a lot of kids do and it came back to bite him. He was able to work out a deal in regards to paying support but I’m not sure what it was. Personally, I think she was more at fault for not telling him she was pregnant than he was for ther resulting problems.

        1. HR U of Me*

          Agreed. If you do the math, not shocking at all. It will be far less shocking if a wholesale reduction in reproductive freedoms, including access to birth control, happens, as it does NOTHING to deter odious behavior.

          OP has a few options for next steps without bringing too much of the drama front & center. They can ask for a transfer or admin leave while HR investigates and sorts it out, if the boss isn’t placed on leave pending the outcome of investigation.

        2. Venus Supreme*

          I’m not surprised she had the child. I’m surprised that, when told about her pregnancy, OP’s boss didn’t realize the severity of his actions and choose end the infidelity there.

        3. bridget*

          Yes, but I am always surprised that people whose lives could be blown up over the consequences of a pregnancy (much more so than a non-procreative affair) aren’t extra super duper cautious about preventing pregnancy. Obviously this guy isn’t the sharpest (in addition to being a slimebag) but I’m still baffled he didn’t have at least that much common sense.

          1. Zombii*

            Some men don’t consider birth control their responsibility or concern.

            Some women don’t consider birth control their responsibility or concern.

            And sometimes these people find each other.

        1. Venus Supreme*

          When I read that, I interpreted as the mother of the child cares deeply for Boss and possibly intends to have a life together with Boss, maybe even a family? Maybe marriage? Which also means to me she doesn’t know how slimy he truly is.

          Or, maybe, he has a really cool name and she wanted her son to have that name too. Could go either way.

          1. Temperance*

            I honestly took it as her trying to usurp the wife by giving him a namesake. Sad, weird, and kind of gross. I mean, she has to know that he has a wife unless she’s really stupid (like seeing him during the workday and for motel trysts only).

  48. emma2*

    I just read the synopsis of an entire soap opera series!
    Not that I am an expert in these matters, but from the perspective of the OP as an employee, it is probably conventional wisdom that she doesn’t meddle in their marriage, mostly because it might jeopardize her job. However, if she doesn’t care about her job and has the urgency to alert the wife, she could justify doing so on the basis that the boss forced her to get in the middle of this in the first place.
    As for alerting the spouse that is being cheated on – I have heard a 50/50 divide. I imagine that if I were the wife, I would want to know my husband was cheating on me so that I could cease wasting time with what is a horrible sleazebag. But as Alison pointed out, there are a lot of people in the second category.

    1. Jamie*

      Or people who want to know, at least in theory, but wouldn’t immediately react well to the OP.

      If I was not suspicious of my husband of cheating and his assistant brought it to my attention…unless the relationship were such that I would take her at her word my reaction is not going to be gratitude off the bat.

      I’d hope I’d be civil but I’d be side-eyeing both of them to figure out if he was cheating on me or she was messing with my marriage for who knows why. There is danger in being the messenger. I’d risk it for my sister or a personal friend…but that’s it.

      1. emma2*

        Yeah – I agree with the people suggesting that the OP treat this solely as a work issue – so complain to any higher ups/HR in the company, but stay out of the personal stuff. When I read the post, I thought it was very possible that the slimeball was the owner of his own company hence why he was taking so many liberties – but the fact that he is covering up his finances means he has to be accountable to someone.

  49. Katie the Fed*

    Personally, I’d inform HR. He’s misusing company time, company resources (you/credit card) and potentially putting you in hostile environment by sending you to a massage parlor.

    HR can deal with him.

    1. Engineer Girl*

      I agree with this path. Going to HR will help protect her job if HR has any sense at all.
      My concern is that the OP will be accused of
      mischarging and timecard fraud for the time spent covering these activities.

      1. Natalie*

        Although if OP has a nonsensical HR, they’re already at risk should anything come to light in another way. Bringing it up pro-actively at least allows OP to avoid the impression that they’re just covering their ass.

  50. AdAgencyChick*

    Count me in the “go to HR if it exists, AND if you trust them to protect you.” My cynicism is based on a previous company I worked for that took care of higher-ups who were notorious sexual harassers. Don’t ask me how one gets away with it in this day and age — I suppose that HR department just counted on the accusers being so discouraged by the length of time needed to pursue complaints through the legal system that they’d look for another job. Sadly, it worked.

    If there is no HR or you don’t trust them to lay down the law with your boss AND be watching him like a hawk to see whether he retaliates, I’d look for another job, and out him to his wife if you choose after you’ve found one.

  51. Anomyous*

    I have never cheated on my wife. However, she has told me more than once that she did not care if I “ran around” as long as she never found out. So, it is entirely possible that his behavior is perfectly within the arrangement he and his wife have. That alone is reason enough not to tell her.

    As for the expense stuff, it sounds like most of what you are being asked to do is not out-of-bounds for what an administrative assistant might be asked to do. Even the strip club thing is not all that out-of-bounds for some industries. I know of one industry where salespeople (including women) regularly take buyers and potential buyers to strip clubs and pay for it.

    It also sounds like the company is happy with his performance. Perhaps he brings in big accounts. All of the extra “activities” have to be cutting into his time and yet the company continues to keep him so they see more positives in him than negatives.

    My advice: continue to do what your boss tells you to do unless you feel like it is uncritical or against corporate rules, keep your mouth shut, look for another job if all this bothers you too much, and keep your head high because you are doing nothing wrong.

    1. Karanda Baywood*

      It’s already blasted through all corporate norms. And yes, she’s doing something wrong in that she’s covering up for his financial finagling.

  52. Grits McGee*

    OP, it might be useful to think out the courses of action available and potential consequences to help you make a decision. For instance, if you told the wife and she was glad to know, and then you were fired, would it be worth it? Or, if you told the wife and she refuses to believe you/didn’t want to know, and then you get fired, would it be worth it then? Or, if you don’t tell the wife, she finds out and is devastated she didn’t know sooner, but you keep your job, would that be worth it? Ultimately, your boss’s reaction, his wife’s reaction, HR’s reaction, the mistress’ reactions, are all out of your hands- what are the consequences that you can live with?

  53. Merida May*

    OP, I’d consider getting out of this situation entirely. For your boss, lying and manipulation are essential components for him to function on a daily basis, and as long as you work for him you’re probably going to be placed in uncomfortable situations to facilitate this. Honestly, the fact that his dirty laundry hasn’t been aired yet is dumb luck, as he seems to be doing just about everything in his power to get caught. Bringing his girlfriends into the office? Involving his direct report in booking hotel rooms/covering up his tracks? Accidentally using his company credit card at a massage parlor? Fathering a baby with one of his mistresses?! If he uses the free space he’s already filled up a row on his sleaze bag bingo card. I understand the feeling that you have a duty to tell his wife, but your boss is such a mess I’d be concerned about retaliation and what that might look like coming from him.

    1. Karanda Baywood*

      Unfortunately, it may end up looking like OP is complicit with his misdeeds if she continues much longer.

  54. Tex*

    Talk to HR…if they are trying to get rid of your boss this might be the smoking gun. Of course, they won’t tell you directly so try and suss out their intentions by asking what you can do to mitigate not getting yourself in trouble with the company’s policies.

    Second, if you don’t see HR having a problem with his behavior, suggest to your boss that he get an outside Personal Assistant to do his personal shopping, errands like the credit card, dinner reservations, etc. Tell him it’s a liability for the company for you to do this and you don’t feel comfortable but that you will coordinate with this person. Maybe hand him a list of candidates that provide such services. Obviously, discretion isn’t a problem for him so letting another person in the loop may not be embarrassing; he might give you pushback to continue with things as they are because he’s being cheap about the expense or it’s just too convenient to have you mind the details of his professional and personal life.

    But don’t tell the wife. That’s not your burden.

    1. Karanda Baywood*

      Maybe hand him a list of candidates that provide such services.
      ……

      You mean encourage another person in the organization to take over the ick?

      1. Tex*

        No, I mean other services outside the organization. There are people who work as part time PAs on an hourly basis.

  55. Viola Dace*

    Ugh. I was in a similar situation once. Worked in a family business for the husband and wife owners. Their sons worked for them. The husband was having an affair with his son’s admin. It was pretty obvious and I will tell you the wife KNEW. I’m sure the OP’s boss’s wife knows and the OP should stay the hell out of it. The worst of it for me was when everyone outside the family and the business started to catch on. Because boss/husband had super obvious vanity plates (like, his name FFS) and he and the admin used to park in public places and make out. People starting asking me about Joe Schmoe Sr. and whether or not they had actually seen him slobbering all over a woman not Mrs. Schmoe while parked in a Safeway parking lot. They were very well known in our town and it was really, really awkward.

  56. she was a fast machine*

    The only thing that bugs me about all this is the potential STD factor. The wife is already compromised in her health, and there is concrete evidence that the boss is having unprotected sex with these women. An STD could quite literally cause serious health problems for the wife, up to and including death depending on the seriousness of her condition. I completely agree that it’s really not OP’s business, but I have to admit, were it me, my concern over his wife’s health would probably push me over the edge of anonymously telling her.

    Realistically, I see the options as going to HR, if possible, or, as Mike C suggested, informing him that you will no longer be covering for his non-work activities and won’t be running any more errands for him.

  57. Marisol*

    Some questions for the OP to consider as she decides on a course of action:

    How easy is it for you to get another job?

    How much do you like your current job, distasteful situation notwithstanding?

    What sort of relationship do you have with your boss? Can you speak frankly to him? Does he allow you to push back, or is he completely authoritarian?

    How important is it to have a good reference from this employer if you do leave?

    How well do you know the wife? Are you close at all?

    My only counsel to you, OP, is that you not see this as a black-and-white thing moral issue, and be sure to consider well how your actions will affect *you*. I would hate to see you rush off to tell the wife because you think it’s morally right, and shoot yourself in the foot by doing so.

  58. LadyPhoenix*

    1. Go to HR/Company CEO with a list of all the expenses, traveling, purchases, and dates and times of the women’s visits. You can ask for protecton from retaliation, but it is not a gurantee. Ask that in case you are fired, that they can provide you a positive reference and unemployment
    2. Go job searching. If this place burns, then you need to be outta there
    3. Once you are out and you know the wife is ok, you decide whether to tell her or not. Just realize that if you do, don’t expect thanks or even belief.
    4. Be careful of your boss trying to sue you if they divorce, I heard that is a thing (though I think it only applies if YOU were the mistress). Whether it applies or not, the court case will be a pain

    1. LadyPhoenix*

      Oh, and a step between #1 and #2, tell your piece of garbage of a boss that you refuse to cover for his affairs anymore. That is not in your job deacription and most of his duties for you border between sketchy to illegal.

  59. Jill*

    I wouldn’t tell the wife. You never know what goes on in a marriage or how the wife will react.

    I would discuss the matter with HR (like AAM said, in case he threatens her job). And then I would set some serious boundaries. OP sounds like a atypical assistant that often runs personal errands in with the work related ones. But that doesn’t mean you have to do anything shady. Tell him you will no longer run errands or do tasks that involve booking nooners at motels, or picking up trinkets, and certainly nothing involving going to strip bars or massage parlors. Just refuse to do any task that has nothing to do with the actual business you work for. If he protests, go to HR. This isn’t sexual harassment, per se, but asking your assistant to help you facilitate and cover up an affair comes up pretty close to it.

  60. Anonymoose*

    Anybody else totally blush when they read this? Dear lord, that man has brass calls. You sent your assistant to a MASSAGE PARLOR to pay your bill in cash?

    Dude is insane. Either that or this is actually from the 1960’s or a Mad Men episode.

  61. SoSad*

    Please, please tell the wife. She’s being gaslighted and most likely financially abused. She is absolutely entitled to full information about her own life so that she can make decisions that are right for her. Right now she doesn’t have the complete picture. The excellent Chumplady covered a situation similar to this (vulnerable wife, although for different reasons) and the overwhelming commentary from other betrayed spouses was that they wanted to know. See https://www.chumplady.com/2017/01/dear-chump-lady-tell-pregnant-sil-husband-cheating/.

    If you are going to tell her anonymously, give her as much evidence as you can so she takes it seriously. This guy is a total scumbag and she needs to get far, far away from him.

    1. not a nonnie*

      +100, I know this goes against everything everyone else is saying, but holy hell, yes. STDs have serious health consequences, especially for people who are experiencing other health complications.

  62. AnonMinion*

    Have we already met the Worst Boss of 2017?!

    OP, I am so sorry you are going through this! How awful! Run, don’t walk, from this job!

  63. Greg*

    This is an extreme example, but here are some guidelines to follow any time you’re asked to engage in unethical and/or illegal behavior at work:

    * The most important thing you can do is leave the situation as quickly as possible. The longer you stay, the more likely you are to be ensnared by whatever is going on.
    * Document everything. Don’t use company resources to do it, and keep everything offsite/in the cloud so that your access can’t be restricted.
    * You probably don’t want to be a whistleblower. Yes, there are scenarios where your obligation to the greater good will supersede everything else, but the fact is, things almost never turn out well for whistleblowers, even in cases where there was clear malfeasance and the whistleblower was completely in the right. A single person taking on a large institution is like a bicyclist taking on a Mack truck. If you get in their way, they will run you over. If you feel it is important to blow the whistle, know ahead of time exactly what you’re getting into.

  64. NotMe*

    I have not read all the comments so forgive me if what I say is similar to others’ comments.

    I have dealt with a very similar situation in the past, only as HR that an assistant came to. My advice to the OP is to tell your manager know that you are not comfortable with the current situation. “Boss, this has been bothering me for some time, but some of the tasks you ask me to handle that are related to your personal life make me uncomfortable. Specifically, when you ask me to lie to your wife, make personal hotel accommodations or buy personal gifts for your “friends”. As of today, I ask that you no longer put me in these situations.”

    If you are afraid of repercussions from your manager and/or have a good HR department, report this situation to them immediately. As I said, I have dealt with this before and have intervened which resolved these issues for the staff member.

    1. NotMe*

      Oh, and no you should not tell the wife. Your goal is to not be involved in your boss’s affairs. By telling the wife, you are getting more involved. You need to ask yourself what your goal is. Is it to out/punish your boss or is it to not be involved in this slimy behavior.

      3. Not So NewReader*

        Thirding. It’s not up to you to save the world, OP. First get yourself to a better place. Figure out what it will take to do that.

    2. Rocky*

      I was hoping someone would say this! Thanks NotMe. It’s so important for OP to be strategic about what will bring her the best outcome. That is a separate issue from any moral/personal concerns.

  65. Jeanne*

    I usually don’t like to say this. I think you need to put all your energies into finding a new job. This guy is icky. You obviously can’t change him. I don’t think you should be involved in telling his wife. The thought of my boss having sex in his office while I have to lie for him just completely weirds me out. Keep on doing your regular job duties like reconciling the credit card or holding his calls. I think if he asks you anything like going to the strip club to sort out his messes, you should calmly say “I don’t feel comfortable doing that. I think it would be better if I don’t get involved.” But you need to get out of there. Get a job, get transferred, anything.

  66. A Bag of Jedi Mind Tricks*

    Wow! I feel bad for the OP and shame on her boss for dragging her into his “shenanigans.” What he does in his personal life is his business, but he’s bringing his personal life to work (having the other women meet him in his office; having his employee go shopping for gifts for them, etc). He has no right getting OP involved. I think OP should definitely get HR involved and as best she can, remove herself from this bad situation.

  67. Greg*

    Oh, one other thing: Stick to documenting facts, with no conjecture. So even though your boss is almost certainly having sex with his mistresses in his office, don’t say that. Just say, “He brings women into his office, closes and locks the door, and asks not to be disturbed.” First of all, anyone with a brain will draw the correct conclusion. Second, you avoid getting yourself into trouble by saying something you don’t know for a fact (and if you did ever, um, walk in on them, just say that as well: “I entered the office and found both of them in a state of undress.”)

  69. Robbenmel*

    1. The Wife may be entirely clueless, or so in the know Boss shares details with her, or anywhere in between. It doesn’t matter. Their circus, their monkeys.
    2. OP should absolutely not say a word, because #1, and because Shoot the Messenger is a real (metaphorical) thing. Also, Shoot the Spouse is a real (literal) thing, as I discovered when I found myself facing a shotgun after someone sent an email to my now-ex. Thank God he didn’t pull the trigger.
    3. OP should be getting the heck outta Dodge, either within the company if s/he can and wants to stay, or outside (which would be my preference) because #1 and #2. Just get away from Boss.

  70. BTW*

    I think people are missing a very important point in the letter …

    “I know a way I can out him to his wife ANONYMOUSLY.”

    IMO, that changes the game. It’s tough. I’ve been there. DH told me that one of his friends was cheating on his then fiancee, now wife. I wasn’t exactly friends with the wife, actually I’m not at all, but I would want to know. The only reason why I didn’t say anything was because DH asked me not to. He didn’t want his friend to not trust him. And so I didn’t. DH made a decision to share that information with me when he didn’t have to. And he was sharing because he too, didn’t think it was right. But by out-ing the friend I would be betraying my husband’s trust and I wasn’t about to do that. On the same hand, this friend has cheated on almost every gf he’s had. He’s not the brightest crayon in the box and any woman who actually agreed to marry him has got to be pretty dull either.

    In this case, I wouldn’t feel any moral obligation to the boss. I would stop doing his dirty work for him (actually I wouldn’t have started in the first place) and if I could truly do it anonymously, I would out him in a heartbeat. But … that’s just me. At the end of the day OP even if it IS anonymous, he might figure it out. I would …
    1) Tell him you’re not doing it anymore
    2) If he puts up a stink about it, contact HR
    3) If no one does anything, find a new job

    My old boss cheated on his then gf, now wife, all the time. I didn’t know specifics but it was common knowledge. Everyone knew. They’re married and have a kid and I’ve heard he’s still at it. I feel like she knows though and just turns a blind eye to it.

    1. Not So NewReader*

      I am afraid that the OP would out herself with the anonymous tip by accidentally letting a piece of info fly that only OP would know. All it takes is one slip up, OP. You have weigh out which is more important, saving the wife or saving yourself.

  71. JennyFair*

    I am not sure if I would tell the wife (I’ve been the wife), but I would sure as heck look for another position, because if he’s that brazen with his behavior, there’s a fair chance people would assume I was sleeping with him (assuming here that the OP is also female) and that’s a difficult rumor to overcome.

  72. AcademiaNut*

    When it comes to the telling the wife discussion, I tend to use two questions to determine if it’s a good idea.

    1) How likely is it that they will believe you?
    2) What is the likely fallout for telling?

    Anonymous letters are not believable. The chances that someone is going to upend their life and kick out their spouse based on the claims of an unsigned letter are very small. So for the OP to have any chance of being believed, she has to do it under her own name and position. It doesn’t sound like the OP has a close personal relationship with the wife, so the wife doesn’t know how trustworthy the OP is, and what her motives are (genuine concern, causing trouble, a vengeful ex herself). And the OP doesn’t know the wife well enough to know if she knows about the situation and has accepted it, or is totally in the dark, or kind of suspects but is not ready to admit it to herself, or is this close to kicking him out, or hates it but is staying for the health insurance.

    For the fallout – if the OP tells the wife, the likely fallout is to be fired and possibly other retribution (badmouthing her to reference checkers, trying to deny UI).

    So to me, that adds up to telling the wife being a lot of risk for little chance of success.

    For the rest – what it mostly comes down to is the OP being asked to do stuff by her boss that is legal but morally repugnant. If the upper management is likely to be sympathetic and supportive, then she can go to them to see what to do next. If they are likely to back up her boss (and there are definitely work cultures like that), then her best option is to find a new job.

  73. Narise*

    Out him to your employer first and see how it goes. Having to go to strip club or massage parlor seems borderline in an office setting. Either way update your resume and get out or transfer as fast as possible.

  75. Christmas Carol*

    Here in Michigan two of our “honorable” state legislators (both married to other people, and both self-avowed conservative members of the “family values” party) decided to have an affair a couple back in 2015. Sadly, much hilarity ensued, including one “fake blackmail” plot, in an effort to hide the recreational activities….and at least two legislative aides were fired for failing to help with the cover up. Karma being what it is, they were found out. I don’t have the time to look up the details right now, but by the time it was over (but I don’t think the legal wrangling is done yet) one representative resigned and the state House of Representative kicked the other one out. (They both swore “the people” would return them to their former seats in the next election. The people did not) The aides got their day in court, plus at least 15 minutes of fame, people were charged with misuse of public funds, and everybody is still threatening to take everybody else to court. You can’t make this stuff up.

  76. Robbenmel*

    I’ve thought and thought about this, and I referenced this thought above, but I feel the need to reiterate.

    OP, if you’re still reading, please don’t try to out anybody. People go crazy and get killed over this kind of stuff all the time. It’s not worth it.

    Please don’t.

  77. Greg*

    One more reason not to drop a dime on your boss: These types of serial philanderers tend to be very good at manipulating people; that’s what they count on to bail them out of their reckless behavior. If you take this guy on (even anonymously), unless you have him absolutely dead to rights, he may be able to wriggle out of it, and possibly even shift the blame onto you. That’s why the best thing you can do is remove yourself from this toxic situation as soon as possible.

  78. 2horseygirls*

    Is “No” not a complete sentence anymore?

    OP: “No, I will not go pick up your mistress’s jewelry.”

    Sleazy Boss: “I will write you up for failure to complete job duties.”

    OP: “Really? Let’s mosey down to HR, and see if “picking up jewelry for Boss’s pregnant piece on the side” is in my job description. I might have missed it. We can probably ask VP of HR to have List of Demeaning and Immoral Duties added to my job description at the same time.”

    I acknowledge that it’s very easy to be flip and sarcastic behind a keyboard, but honestly? I can’t think of another response.

    I’m sorry, OP. Good luck on your job search! Getting out of there is the only way to extract yourself from this, it seems.

  79. Jamie*

    Most of the comments seem to be focused on the boss’s affairs (not surprising) but I’m wondering about the OP re-calculating business trip expenses. What does that entail? Is OP including ‘business expenses’ that shouldn’t be included?

  80. Johnny*

    My good friend who’s gay has an uncle who’s a pervert. The uncle wanted nothing to do with him, never called to wish him happy birthday or happy Christmas, etc. Basically took no interest in him whatsoever. I feel for him because the mum’s a total bitch, coming to grips with the fact he was gay was the least of his worries. When he told his mum he was gay she asked why did you choose to be gay? Then she goes and blabs to the entire family and somehow the uncle finds out and now all of the sudden wants to play nice and be all buddy budy. Turns out the uncle wants to get into his pants. The uncle tells him not to mention any of these conversations to anyone, at first I thought it was odd because why would he want to keep it a secret about two guys talking, come to find out that the uncle wanted to keep secret the fact he was going to cheat on the wife with another man, and that man was none other than his own nephiew. My friend comes to me and asks what he should do, whether or not he should keep the secret or tell the wife, aka his aunt. Needless to say the relationship with the aunt is shot because she’s a bitch pretending to be all nice and caring, didn’t wish him happy birthday, etc. The relationship with the uncle is done. I told him listen, leave the pervert alone, if he can’t be honest with himself or his wife, it’s gonna blow up in his face. Be prepared to find a new job, you don’t need that dirtbag around.

  82. Indie*

    So I agree that women are not society’s caretakers and therefore an escort is allowed to be business like and uncaring about a female stranger.

    But by the same token so is the wife! She doesn’t owe the escort any caring or considerations either. No silence owed. No sleepless nights either.

    If a man found out that a gigolo had been given large sums of his marital funds behind his back, do you really think he would not consult a lawyer or do everything in his power to make the gigolo think ‘not worth it’ and back off? But because this betrayed spouse is a woman there is a sickening expectation of demure lady like forgiveness. “Oh don’t worry about the money dear. Keep on billing! Otherwise your pimp may get violent”. Why she would be ‘bitter and vengeful’ if she failed to be a caretaker for her husbands sex workers.

    Come on. A violent man’s actions are his fault, not the responsibility of a woman outside the transaction! Also there is a LOT of patronising and paternalism going on toward the escort. I’m sure she knows the pitfalls of her own profession and if she does not then she’s relying on Goodwives being seen and not heard.

  83. partgypsy*

    this is from the perspective of a wife who was cheated on. I didn’t know, in part because he separated me from his activities, and was good at lying. However what was really upsetting, is I reached out to a couple of mutual friends and one of his family members. One of the friends didn’t know (he didn’t tell him) and said he couldn’t imagine he do something like that, one friend simply didn’t get back to me, which should have been a red flag (this friend knew and this was their response), and the family member bald faced lied to me about that and other things. Yeah my ex lied to me, but the fact that the family member lied and covered up for him, was really despicable and a mind f*ck.
    My advice. You can’t control what your boss does, but you can decide what YOU do. I would keep in mind yes whatever you do can have job consequences but you sound like a very competent person and should land on your feet. Let HR know about the boss using your time for non-work activities. Clarify with them about uses of expenses and corrections. You can frame it you want to make sure you are following procedures. Most of all, tell your boss that you are uncomfortable doing these activities for them, they are not part of your job, and you are no longer going to do them. If he fires you, then let everyone know what you were fired.

  84. partgypsy*

    Oh, FYI in case it wasn’t clear, yes I would have want to know. Not saying the OP has a moral obligation being a stranger, but there may be a moral obligation if you know or are friends with the person being cheated on. In this kind of situation, some piece of evidence to pass on, like a receipt of purchase of jewelry, copy of birth announcement, etc is useful while “I think your husband is cheating” note can just add wonderful and on cheater’s part to plausible deniability. It was only when I found proof I was able to move on after being in limbo for a long long time. For the person who does pass on information, don’t concern yourself what that person does with the information. that’s their business. You just need to decide what you need to do based on your own moral conscience.

  85. Rising Above*

    Poor OP. She needs to run, not walk, from this toxic job. Her boss is a pile of steaming excrement and the longer she remains with him, the more she will be emotionally disfigured by him. I would not inform the boss’ wife. She will eventually learn the truth, and I can only hope she will engage a good divorce attorney who will insist upon production of his credit card bills. I can only hope that OP’s name is not on anything obtained under discovery.

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