Dear John: I Think My Boss Is Having An Affair
Tuesday, May 07, 2013
Dear John,
I am the administrative assistant to a man who’s very powerful within our company. Our relationship is strictly professional, but he relies on me to do a lot of non-work-related things – buying gifts, finding dog-sitters, etc. I truly do not mind doing personal things for him. He works very, very hard, he’s unbelievably good at what he does, and his job and personal life are so intertwined, that in a way, it’s all work related. If not for what I am writing to you about, I would be very happy in my job.
For about a year, he has been asking me to do things that lead me to believe he is having an affair – reserving a hotel room in town for him for a night, purchasing gifts that seem personal but that I know are not for his wife, requesting that I not tell his wife certain things, etc. Over the past twelve months it’s really added up. I cannot think of a remotely plausible explanation except that he has a girlfriend.
In the three years I have been working for him, I have become quite friendly with his wife. I am in my 30s and they are my parents’ age, and whereas her husband is a bit remote, she has always been so warm and kind to me. She was especially thoughtful when I was going through a very difficult time, and I will be forever grateful to her. The thought of collaborating in something that would devastate her is repulsive to me.
I am truly torn. If you knew my boss, you would know that asking him about it is out of the question, and I feel certain I know what’s going on anyway. I just don’t want to be a party to anything that would hurt a woman I respect so much. What would you do?
Sincerely,
Not Going to Assist This
Dear N.G.T.A.T.,
I’m glad you asked what I would do instead of what you should do. I can tell you what I would do, but you’re going to have to decide for yourself what you can live with.
There are a lot of ways you can handle this, but it comes down to a clear choice: Suppress your feelings and continue to do your job well. Or find another job.
There are an awful lot of unknowns here, the foremost of which is that you are not certain your boss is having an affair. Your inability to think of another explanation for the things he asks you to do doesn’t mean there isn’t one.
But let’s face it: his having a girlfriend doesn’t exactly defy belief. If he does, though, so what? His wife may know about it and not care. She may dislike it but accept it as the price of the life he provides. They may both have lovers. You really have no idea what their domestic life is like.
Let’s take it a step further and assume your take on it is precisely right. Again, so what? You’re his assistant, not his conscience. Are you afraid his wife will find out and ask you why you didn’t tell her? It would be completely unreasonable for her to expect that of you. She may have been kind to you, you may be friendly, but you are not friends from what I’ve read here. I think you’ve gotten a little too personally involved in this.
In fact, I think it would be a mistake to talk to either one of them, if that’s a course of action you’re considering. Bringing this up with a remote, powerful boss old enough to be your father would not only undermine your current job, it could threaten your chances of getting another one.
Back to your question: if it were me, I would forget about it and go about my business. If you simply can’t do that, though, look for another one. But don’t weaken your prospects by getting any more deeply ensnared in this. These people’s private lives are really none of your business.
Dear John,
I’m worried about my best friend. We both are recent college graduates and are working in hipster retail until we figure out the next step, most likely grad or law school. While we were in school my friend and I both got tattoos. They are small and in a discreet place. Since then, my friend has started to get tattoos on a regular basis. She has quite a few of them and they are very noticeable. It may be unrelated, but she started to get more after her parents’ recent divorce. Her parents don’t like the tattoos and I think it may be her way of getting back at them. I mentioned that and she got very angry, so now I don’t say a thing. I know it’s her life but I can’t help thinking about all the negative consequences of her tattoos, ranging from how she will look in a wedding dress to future employment potential. I've just been ignoring the new tattoos and not participating in her getting them, but this does not feel right. What can I do?
Thanks,
Ink-credulous
Dear Ink-credulous,
It’s difficult to watch a friend do something you think she’ll regret, but part of being an adult is being free to make mistakes. You’ve made your reservations known, so now you have to accept that this is her choice. Tattoos can be removed (albeit imperfectly, painfully, and expensively), so as mistakes go, there are certainly worse ones.
I think that as her friend, you should worry less about what’s on her skin and more about what’s going on beneath it. It sounds like her parents’ divorce is very painful for her. If that’s not something you’ve talked to her about, you should. Just let her unload. I think a lot of parents who decide to split up think it’s easier on the kids if they’re grown, but that’s like saying a punch in the stomach is better than a punch in the face. It may be, but it still hurts like hell.
Dear John,
My husband and I have been friends with another couple for about ten years. We love this couple dearly and spend a lot of time together. Our friends are empty nesters and about a year ago adopted a dog. I can’t believe how this has changed the nature of our relationship with them. If they drop by they most likely have the dog in the car and can only stay a short while. If we go out, they can only stay out for a specific period of time because they have to be home for the dog. When we visit their home, the dog is ever present, e.g., we are having cocktails and the dog is sitting on my girlfriends lap. Both of our friends seem to infantilize the dog and I find it a little weird and annoying. We are now planning a vacation and they need to find “pet friendly” accommodations. The dog has undoubtedly brought them joy but, honestly, their addition has been a loss to my husband and myself. Do you have any advice as to how I can bring this up without seeming anti-dog or self-centered?
Sincerely,
Petty?
Dear Petty?,
You have to understand that the terms of your friendship have changed. They now have a dog that is apparently filling an emotional need for them, and accommodating the dog (and their indulgence of it) is something you’ll have to do if you want to continue to enjoy their company. I know it’s disappointing, but there’s no sense pining for the way things used to be. I would forget about bringing this up with them because I don’t think it would be productive. (On some level, they probably really do think of the dog as their baby. Imagine lamenting the loss of “the good old days” with new parents!) You’re better off adjusting your expectations since that’s a part of this scenario you can control.
That’s not to say you have to go along with everything they now require. If you don’t like the pet-friendly hotel choices, tell them. Perhaps they would be willing to leave the dog with a professional sitter while you’re away. You might even offer to split the cost of this with them. If they can’t bear the thought of that, though, your days of vacationing together may be over. But there’s no reason you can’t continue to be great friends with this couple – you just have to accept that this couple is now a trio.
John is a middle-aged family man from Providence, Rhode Island. If you learn from your mistakes, he’s brilliant. Write to him at [email protected].
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