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'My boss enlists me in hiding his multiple affairs from his wife. Should I say something?' UPDATED 2X

'My boss enlists me in hiding his multiple affairs from his wife. Should I say something?' UPDATED 2X


Is it better to call someone out and potentially lose your job, or let someone ruin their marriage in front of your eyes?

"My boss enlists me in hiding his multiple affairs from his wife."

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 st#$p 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?

The internet had a lot to say.

Violetta wrote:

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

WorkingMom wrote:

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.

Mreasy wrote:

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?

NotSoNewReader wrote:

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.

A few months later, OP shared an update.

Two days after you published my letter, my boss was served with divorce papers here at work. His wife publicly outed his affairs, and she sent copies of emails and text messages sent between him and the two women he was having affairs with, as well as one of the escorts he was seeing regularly, to some people here at our office (including me), his relatives, and some of their friends.

She also sent these to the two women and the escort, and some of their relatives and colleagues at work. The texts and emails prove that all three of them not only knew he was married but that he was seeing other women besides each one of them.

They also include his acknowledgement he fathered a child outside of his marriage and evidence he used funds from the joint account and his wife’s pay to spend money on them, as well as for the random women he cheated with when he was out of town on business. His wife has filed alienation of affection lawsuits against the two women and the escort he was cheating with regularly.

All of three of them kept calling and coming to see him here at work to confront him after they were outed to people and served with the lawsuit papers, and I heard them talking (sometimes yelling) about it each time and him saying his wife moved out the day he was served with divorce papers and he has no way to contact except through her lawyer (they have no children and she has cut all contact).

I played dumb the entire time and no one, including his wife, has accused me of knowing anything or asked me if I did. Before all of this happened, after reading your response and the responses in the comments, I decided to seriously start looking for another job.

The same week my letter was published, there was an opening inside my company for a receptionist in a different division. The company usually posts jobs internally before they look externally, and since I’m classified as admin and the posting is for an administrative position, I didn’t have to apply and could just put in for a transfer.

They gave it to me, and I have been in my new job for two weeks now. I love it so far. I spend all day on the phone with people or talking with people who have come in to see or meet with my colleagues. The division has over 100 people, so while I have a screen where I can search for people by name and receive memos and things through email, I don’t have a computer that I am stuck staring at for hours a day.

It’s definitely not for everyone but I love dealing with people all day and having no other responsibilities or a mountain of tasks or paperwork to do. My new colleagues have been welcoming and while everyone is talking about what is going on with my boss, no one has brought me into the drama and it only gets talked about around me the same as it would any other person.

I don’t engage in any gossip and I certainly don’t talk about what I know, even though no one has asked. I now have set hours, don’t ever have to work outside of those hours (no overtime or weekends or holidays) and no company cell phone. Since all my work involves dealing with people during working hours at work, I couldn’t do work at home even if I wanted to.

Work is now separate from home, and overall I am much more relaxed because I have a clear line between working and not working and I don’t have to deal with my boss and his drama any more. Thank you for your response to my question and to all the people who were supportive in the comments. I felt better knowing my feelings were valid and I wasn’t overreacting or wrong to be upset.

(Also there was some speculation in the comments about whether my boss could be engaging in some kind of emb**zlement or falsifying because he had me separating expenses. There was nothing like that going on. The company has a policy where they will reimburse business expenses put on personal debit or credit cards. Non-work expenses are not allowed to be on company cards.

So if the company paid for a hotel room when my boss traveled on business and he upgraded to a better room, the company would only reimburse or pay the original room price and he would have to pay for the rest of the upgrade. I would separate personal and work expenses before submitting them. This is in line with the company handbook and everyone always does it this way.

There were no issues with him or me because of it. As for him using the company credit card at the massage parlor, they are legal where we are and since he had the charges reversed the same day and submitted proof of the reversal, the company never had an issue because he followed policy and hadn’t used the card for anything ill*gal.)

People were so glad to hear an update.

Spoonie wrote:

I’m so happy to hear things worked out so well for you! Congratulations on finding a position that suits your needs so well and also for getting away from a situation that was…unhealthy.

JMegan wrote:

That is quite the update. Thanks for sharing, OP, and congratulations on your new drama-free job!

Nan wrote:

I’m happy he got busted, but feel bad for his wife.

I’m glad you found another role at the company and now have work/life separation. And that your job doesn’t deal with other people’s dirty laundry anymore.

animaniactoo wrote:

Well I guess that takes care of whether or not to out him to his wife…

She might have gone a bit scorched earth, but it works for me. Glad your new situation works out better for you regardless of getting away from this situation!

Months later, OP jumped on with yet another update.

My former boss was fired. His wife outed a fourth woman for sleeping with him, same as the others. She works here. Having an affair with a subordinate and the multiple yelling matches with the other three women here at the office was enough to get him fired. The fourth woman was married (unlike the other three) and her husband filed for divorce after she was outed.

She took job somewhere else but left amicably and was not fired like my former boss was. At least two of the women his wife was suing are settling with her to avoid it going to trial. The yelling matches he was having made it clear she wasn’t using the lawsuits as a bargaining chip and would not drop them in exchange for stuff from him.

Now that both he and the woman from here that he was having an affair with are gone, things have calmed down. No one has mentioned the affair in weeks and everything here is boring again.

I don’t mind the lack of gossip and am still enjoying my new job and great colleagues. I got a small bonus at my yearly review because my boss was so happy with my work. I love my new colleagues and they have been nothing but welcoming to me.

(Also there was speculation in the comments in my first update about whether his wife outed the escort for her affair or being an escort. The answer is both. I don’t agree with her actions but I empathize with how much pain the affairs have caused her.)

The comments kept coming.

greymoria wrote:

That's one hell of a wife, executing a plan of social execution so well! She probably had her eyes on OP as well, but kindly understood that OP was stuck in an uncomfortable position with her tasks, as the husband was the boss.

TheDoorDoesntWork wrote:

How the hell does a man balance 4 affairs on top of having a full time job and a wife? Sounds exhausting as f#$k.

Sunflower-and-Dream wrote:

It was a positive update for OP who avoided getting caught up in the shitshow and moved to a better-suited position for her. It was a less positive one for the wife who got to see what a scumbag her husband was and divorce him. But she would have been hurt when she learned the truth about her husband, and I hope she heals and finds a better partner for her.

Bored-Viking wrote:

In my workplace, asking your assistant to handle your personal credit card expenses (not even mentioning to assist in hiding your affair) would be enough for termination. Not even mentioning asking her to go to a st**pclub to refund the business card payment and pay the bill with his personal card...

Sources: Reddit
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