“I Slept With My Boss and I Don’t Want to Talk to Her About it!”

I head a department in an organisation (not sure if that matters) and I am separated from my wife but we are trying to work things out. My boss whom I directly report to is extremely beautiful lady and we have always had this harmless flirtatious relationship; I know she is seeing someone but I thought that nothing could come out of our flirts; however, about six weeks ago we were both delivering a lecture in another country and we travelled together and on the third day somehow the flirt led to us sleeping together. It was a good moment that I wasn’t expecting nor planned for and since I am separated, I don’t feel guilty. We returned to work and everything went on normally — a little awkward initially but everything settled until yesterday when after we finished a meeting my boss out of nowhere said: “Are we just going to keep pretending nothing happened or are we going to figure this out?” As I didn’t know what to say, I smiled and walked away. Thankfully, I am off for two weeks starting today but I am dreading going back.My questions: What do I do? Do I discuss it knowing that I don’t want to? If I do discuss it, what do I say? I don’t plan to be with her. — Oops, Flirt Led to Sex

Why on earth would you sleep with your BOSS — who is dating someone else! — when you are trying to work things out with your estranged wife?! And then, as if that wasn’t enough of bonehead move, you literally smiled and walked away when your boss suggested you discuss things? Oh, brother. Now, not only do you have a marriage to try to work out, your job might very well be in jeopardy. Pro tip: when your boss suggests talking about an issue, talk about it. When you have slept with said boss and the issue she wants to discuss is the sleeping together and you know you don’t want to actually have a relationship with her and you want to try to work things out with your wife, you most definitely, absolutely talk to your boss!!

What you do now: as soon as you get back to work, reach out to your boss and apologize profusely for the way you handled things yesterday and the preceding weeks. Tell her that your behavior was a reflection only of you and not the respect you have for her and you are fully aware she deserved a conversation much sooner and you are sorry you didn’t have the wherewithal to give that to her. Explain that you’ve always admired and respected her professionally, and have enjoyed her company personally, too, and that on your trip the lines got blurred and you apologize for any awkwardness or discomfort that may have ensued. Tell her that you’ve been separated from your wife but have recently moved towards trying to reconcile, which means that you are not in a position to pursue any other relationship romantically but you hope that you and your boss can continue to enjoy a respectful and friendly professional relationship, and if there’s any reason you should believe otherwise you hope she will discuss it with you.

Also, not for nothing, but if your instinct is to shrug and walk away – or, in this case, smile and walk away – whenever you are approached about a topic you don’t feel like discussing, you should probably talk to a therapist about this, especially as you and your wife are trying to reconcile.

I’m 21 and lately I’ve been have issues amongst my family. My mother and my step-dad (who raised me in place of my father) got a divorce and she started dating a man whom she called my uncle for 20 years. Talk about confusing? Then, my sister divorced her husband of two months, and started dating my bio-cousin’s dad, another man we’ve called uncle all over our lives. Now my step-dad’s got a girlfriend, and she’s living with him, and now I hardly ever see him, because he’s too busy spending time with her two kids. He cancels almost every time we make plans, and when I do see him, it feels awkward, and it’s hard to talk to him. Yet, he gets upset when I try to communicate this to him.I just feel like my heart is full of storms, and I can’t understand why this is happening to my family. We’ve always been a close family, we even all lived in one house together just a year ago. Why is this happening? What makes everything change in just a year? I’ve been told that I don’t understand because of my autism, but I don’t think that’s it. Please help me understand. — Confused Abut Family Musical Chairs

What if, instead of focusing on understanding, you focus on honoring your own self, your needs, and your boundaries? Whom your mom and your sister date isn’t really any of your business. Is it weird for you that they’re dating men you’ve called “uncle” most of your life? Yes, apparently it is. It may be weird for a while. Eventually, if these relationships continue, you’ll get used to it. You don’t mention anyone feeling hurt or bothered by these relationships, so if it’s just a matter of you feeling confused or weirded out, eh – so be it. There are worst things to be.

As for your stepdad’s behavior, that’s more painful because it actually affects you, is reflective of a relationship you are part of, and he dismisses you when you try to communicate your feelings. My advice would be to try a different means of communicating to him. How have you approached him so far? Is it face-to-face? Maybe that overwhelms him, and he’d be more responsive on the phone or through email, where there’s a layer of filtering that may feel more comfortable to him. Remind him how much you love him and how much he means to you and even though you appreciate he is building a new life for himself now and you are happy for him if he’s happy, you still want him in your life and you hope he makes a space for you in his.

You don’t say how old his girlfriend’s kids are, but if they’re young (younger than you) and they live with him, that would make him pretty busy. Raising young kids is incredibly time-consuming and exhausting, and the truth is, his availability is likely to just not be what it used to be. That doesn’t excuse him from canceling your plans all the time, but if he’d adjusting to a new normal, you need to cut him a little slack for that. Ask him if there’s a time in the week or the month that he can set aside just for you, whether it be a regular lunch date or going to the movies or something else that you might enjoy together than would allow you to catch up a bit and stay connected.

Finally, try not to take all of this too personally. Change can be difficult for any of us. If you have autism and you thrive on routine, a disruption to that routine or to what you’ve always known and expected can feel especially jarring. Honor your feelings while also appreciating that not everyone experiences the same feelings or with the same level of intensity that you do. Do things for yourself that make you feel good – exercise, get plenty of rest, eat healthfully, pay attention to your own needs. You are growing up, and while your family will always be important to you and those relationships should continue to be fostered, your dependence on your family to have your needs met should start easing up a bit and you should look inward or towards other relationships to meet some of the needs formerly met by your parents and other family members. Them being less available to you doesn’t mean they love you less – it simply means they are honoring their own needs, too. While specific details are different for everyone, this is a normal part of growing up.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. Avatar photo Prognosti-gator says:

    LW1: “somehow the flirt led to our sleeping together.”

    *Somehow* it just happened, huh? You were working on your presentation, trying to copy a block of text and instead of hitting Ctrl-C, you accidentally hit ALT-Ctrl-C which resulted in finding yourself in mid-coitus. I mean, it happens.

    The way you’ve handled this is so childish. You don’t take any responsibility for any of your actions. You act as if you had no part in sleeping with your boss (it just *happened*) – and when she brings it up, you just smile and walk away like she’s a T-rex who might not see you if you just stand really still. I’m not saying anything even needs to come of this (sleeping with the boss is stupid, especially when trying to work through a separation) but you at least owe it to her to discuss it.

    1. Really. The whole narrative is very immature and unaccountable. I’d hate to be either the boss or the wife.

  2. I’m at a loss why you felt the need to tell us that your boss is an “extremely beautiful lady”. Regardless of how good looking she is or isn’t, if I were you I wouldn’t jump to the conclusion that she wants to be with you, she just realises that what she/you did was inappropriate and wants to make sure you and she can work together in the future without awkwardness. And possibly, as she is above you in the power structure, that you don’t feel that she pressured you or anything. So discuss it with her and sort it out when you get back.

  3. Flirting somehow led to sleeping together? You were not in a middle of a lecture and then all of a sudden like a magic trick, you woke up in bed with your boss. What the hell. And the smile and the walking away is not the answer when someone wants to know where this relationship after sleeping together. Just why? If you want things to work with your wife, then focus on that. If you want to fix your marriage, don’t chase after other women, especially your boss.

  4. Bittergaymark says:

    LW1) Eh… I can honestly say I actually can see how flirting unexpectedly led to sleeping with somebody. If I had slept with everybody I ever flirted with —- damn. Woowee! Would I have had a wild time. Hmmmm. Still one more thing to regret maybe. EVERYBODY! Listen up! Trust me! Go sleep with MORE people in your youth!!! Okay, public service message over. That said, LW. You handled this very poorly. Wendy already read you a letter perfect riot act. Why follow perfection? Heed her advice. Smiling dumbly is usually a pretty dumb strategy. Unless you’re Ivanka Trump,
    LW2) Yikes — your family sound like a slutty exotic foreign film. MUCH ADO ABOUT UNCLES. Or maybe TODOS LOCOS DE LOS TIOS. Yeah, your stepfather is not doing right by you. But all you can do right now is focus on yourself and getting yourself eventually away from all this madness. PS — Your autism has nothing to do with your confusion here. You are in a mighty confusing situation .

  5. You smiled and walked away… this… what… no. Put your big boy pants on and have a conversation with her. I wouldn’t wait til you get back in the office either. Arrange to meet her for lunch or something and get that awkward conversation out of the way IMMEDIATELY.

    1. And what’s with the “do i discuss it even though i don’t want to?” LW1 you’re an adult (presumably) and adults have conversations even when they don’t want to. I can’t understand why you felt you could completely ignore your boss and “smile and walk away.” It doesn’t bode well for your career if you routinely ignore your boss when she asks you a direct question and think you can smile and walk away without addressing her.

      1. The Boss isn’t being paid to bang her subordinates and he enjoys the same rights to walk away from unwanted conversations as anyone else.

  6. In the USA at least, many mid size and up organizations ban relationships with direct subordinates. In my company the boss would be immediately fired if this came to light. The subordinate would typically be held harmless due to their perceived lack of power in the relationship, but the reality is that person would be better off moving to a new company for a fresh start unless there was a clearly abusive situation.

    In your case, it was a clearly consensual encounter, and you have no desire to continue the relationship. Your best option if you want to remain at the company is to meet with your boss and suggest that the best thing to do from both a professional and personal perspective is to forget anything happened on the trip, and then commit to acting that way.

    If you want to remain at the company, you also need to stay on the boss’s good side by saying how much you like and respect her, but that you are committed to reconciliation with your wife. You can apologize for being awkward during the first follow up conversation and say you needed time to process what happened and what to do. The boss needs a comfort level that you will not expose her and if she understands that you both have a reason for discretion, that will go a long way. If you don’t get a warm fuzzy feeling that she is willing to forget the whole thing happened, I would move on to another company.


  7. LW 1 – you are an idiot.

    LW2- try to find someone to talk to about all this. It is confusing & messy. Wendy is right, take care of yourself first. You may need help navigating all this.

  8. I try not to harp on these things too much, but it’s impossible for me to imagine you giving a woman who slept with her boss the advice that she’d better continue talking about her romantic relationship even if she didn’t want to, or risk getting fired (with the the chortling implication that she’d kind of have it coming). Among the reasons that it’s grossly immoral for bosses to sleep with their subordinates is that it puts the subordinates in a position of having to continue to engage unwillingly out of fear of losing their jobs.

    LW, speak to an employment lawyer immediately. You need to figure out what your rights and risks are, This will probably be followed up by a trip to HR to advise them of the encounter. Do NOT handle this yourself or have off the cuff discussions with your boss about it. You are in a professionally perilous territory and need the advice of a professional, not a bunch of strangers on the Internet.

    1. Just to clarify, going to HR is contingent on the advice of your lawyer. He/she may advise otherwise and you should follow whatever the lawyer tells you.

      1. Agree. I would never try to navigate a workplace situation like this without talking to my employment lawyer. I did this when I was being sexually harassed by a guy from another department, because it was so important to handle it correctly. Her rates are not exorbitant and it’s worth a few hundred bucks in consulting fees to do things correctly and make sure I’m protected.

        This guy used horrible judgment in sleeping with his boss, but yeah, she’s the superior here and the power dynamic is in her favor.

      2. I mean, yes, it was really dopey to smile and walk away from the boss when she wanted to talk. He would have been a lot smarter to have already consulted someone and figured out a strategy for how to handle it if she wanted to talk, whether that be sitting down with her and making certain statements about how it was a mistake and he doesn’t intend to continue a relationship with her, or saying he can’t discuss it, or SOMETHING. But I guess in the absence of having a strategy to protect himself (maybe men don’t think they need one), walking away maaaaayyy have been better than saying a bunch of off-the-cuff probably dumb stuff to her that may have made the situation worse. What I might do in that situation is stall her and tell her yeah, definitely, let’s discuss this, but right now I really need to do XYZ, and then go out in the parking lot and CALL MY LAWYER.

      3. Yeah, everyone is mocking him for it, but in many cases , saying nothing is often the best policy.

        And he was at his place of work and was put on the spot by his boss to discuss their illicit romantic encounter. The idea that he’s somehow the bad guy for not having some kind of ready and appropriate response to someone who is in a position fire him if he rejects her is wildly unfair.

      4. To be clear, it’s incredibly dumb to sleep with your boss and even dumber not to think about the peril your career could be in or come up with a self-preservation strategy, but yeah, she put him on the spot and he wasn’t prepared. The best stall tactic might have been, “yes, let’s talk about this but not at work.” And then instead of writing an advice columnist, call a lawyer as his next move.

    2. You’re right. I was wrong. Thank you for chiming in with much better advice!

  9. I am going to say this again since several of the posters have repeated the terrible advice to have a heart to heart with your boss. Anything you say going forward could be evidence in an employment or legal dispute and your personal impulse control and judgment has been, shall we say less than exemplary. Speak to a lawyer, follow his or her advice, and don’t have sex with other coworkers going forward.

    1. Bittergaymark says:

      Interesting points, Fyodor. Yeah, I blew it on this one…

    2. Avatar photo Prognosti-gator says:

      I agree that he should talk to a lawyer, because this situation could get ugly, quickly.

      But, nowhere in the letter did he say: “because of the possible legal ramifications, I thought it best to walk away so that I could first determine a course of action with my lawyer.”

      It’s pretty apparent his reaction was just because he just didn’t want to do anything difficult. If he was the kind of person who had foresight and judgement, he wouldn’t have slept with his boss to begin with.

  10. “Pro tip: when your boss suggests talking about an issue, talk about it.”

    Pro-tip, f*cking you on business trips is not part of your boss’s professional purview and you absolutely don’t have to discuss it with her if you don’t want to.

    1. Fyodor, seeing your responses i can see how the right course of action is speaking to an employment attorney like you suggested. I was looking at the situation has him being dopey and not considering the power dynamics at play like i would’ve if the genders had been switched. LW listen to Fyodor.

  11. dinoceros says:

    LW1: Yeah, I’m sure that sleeping with your boss and then trying to ghost her in real-life is going to work out well.

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