“I Had an Affair with my Potential Boss”

I’ve recently interviewed for a dream job in another part of the country. My field is very narrow and jobs like this do not come along often. It’s also in a city that has a lot to offer for me and my boyfriend who would be moving with me (he works from home). We’ve been together for one year and are planning to move in together soon, whether it be here or there. Things between us are wonderful and I know that I have found a true partner in him.

Although I researched the employer before applying, it wasn’t until after I was called to interview that I noticed the name of their newly appointed VP (my would-be boss) as a person I know. I met him nine years ago at a work conference while in my mid-20s. Regrettably, we had a brief affair, despite his being married and long distance from me. The affair lasted one summer over maybe 2-3 encounters. I put an end to it but we remained in regular contact by email for another year during which I tried to transition us into a friendship. But because he remained in his marriage, I think I became the “path not taken” and he struggled to move on.

At a conference later that year, I saw him in person and he had a minor meltdown, lamenting that it didn’t work between us and hating that I had moved on to date others. Since then, over the years, he’s occasionally emailed me and has always been friendly and appropriate (if a bit wistful). He remained married and now has children as well.

I emailed him after I discovered the connection to this job and he was friendly and said he was willing to work together. Still, I sense a tone in wistfulness and nostalgia in his email. I have no doubts in my own ability to redefine our relationship as a working one. I have always admired him as a professional. But one’s relationship with one’s boss is a critical one and I have this nagging suspicion that he still holds a torch for me, crazy as it sounds. If I am offered this job, is it reasonable to think that he can put any old feelings aside so that we can work together? Or would I be foolishly placing myself into a difficult working environment? — Water Under the Bridge

This is really a tough situation, and one in which only very careful consideration will lead you to the right choice. I would start, first, with discussing the issue with your boyfriend. If he’s going to move across the country with you as you pursue this job, he deserves to know about whatever romantic/sexual history you have with your boss and your anxiety around that history. Including him as much as you can in your decision is not only appropriate, it’s good practice for sharing a future together. Bottom line: if you don’t tell him about your history with your boss and it comes out later, after you two have moved across the country, there’s potential for a lot of pain and tension. He’ll wonder why you kept it a secret from him and whether he can trust you.

The next thing you’ll want to do is get as much information about your potential work culture as possible. Would you be working in the same office as your boss? Interacting with him on a daily basis? How many other employees does he supervise? If there’s a chance for you to have a follow-up interview in-person, that would be ideal as it would give you not only a chance to ask these questions, but to see your would-be boss/ex-fling (I’m assuming that the reason you didn’t see him at your first in-person interview is because he hadn’t yet started?). If I were you, I’d even request one more in-person meeting before accepting the position so that you can meet with your potential boss and assess the situation.

Your gut will tell you much of what you need to know upon seeing him again. Please do try to make this happen before accepting a job as his subordinate — even if you have to pay your own expenses to fly out there. If your potential employers see no reason to interview/see you again, you can always say that you’ll be in the area looking at homes/apartments and would they mind getting together for a lunch while you’re there (make sure the ex-fling is included!). As much time and money as this may cost you, it will be worth it before making such a crucial decision.

Finally, if you’ve done all of these things and you’re still unsure what the right move is, then consider what the best case scenario versus the worst case scenario would be if you took the job and which one would have the greatest impact — good or bad — in your life. Make a “pro” list of all the things you hope this “dream job” would provide you. Then make a “con” list of all your fears, including the affect it could have on your relationship. Since you can’t possibly look into the future and know what’s going to happen, you have to be wise and decide whether the potential cons are worth the risk of the potential pros. If the answer is “no,” then you’ll know what to do. Good luck!

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


  1. While I generally don’t think its necessary to share ALL past sexual history with a significant other (people are allowed some level of privacy), in this case I agree with Wendy that you need to tell your boyfriend if he doesn’t know already. If he found out he could think that you moved across the country to basically continue an affair with this guy. While this may be an uncomfortable conversation it’s a necessary one. It may even put an end to any question in your mind about taking this job if your boyfriend refuses to move with you. Furthermore, you should meet with your potential boss in person to assess his feelings. For all you know he may moved on to another affair (married men that have affairs often exhibit their infidelity as a pattern of behavior). On a positive note, I think you have handled this situation as best as possible and I hope you are successful with the move and your career. Just don’t sleep with any more married men! (haha…no but seriously.)

    1. lemongrass says:

      I agree. It would raise some serious red flags if she decided to move with him and didn’t let him know.

  2. artsygirl says:

    LW I would also speak with the HR department. That way you will have disclosed your previous relationship with a superior and you will have the ground work done if he starts harassing you. As you said it has been a substantial period of time since you had your affair with this man and it is possible that he has changed just as you have. Best of luck and congratulations on your new job.

    1. I could not disagree more – why start office gossip about an affair from nine years ago that happened before either of you worked for the company? If she is that concerned that it might cause a problem to be working for him, then she should not take the job.

      1. Guy Friday says:

        Agreed. It was 9 years ago. Suggesting that groundwork has to be laid if he starts harassing her is silly; do you really think HR will take it any more seriously because of their past than they would if they’d never met before and he started hitting on her?

        LW, I think enough time has passed that — assuming you and your boyfriend are still on board with taking this job — you just have to approach this with something of a “clean slate” mentality. I don’t mean that you necessarily FORGET everything he did, but you may want to not start reading between the lines on every sentence simply because of where you guys were 9 years ago. I don’t even know that it’s worth confronting him with a “Let’s be clear that we’re not sleeping together” ultimatum, given how long it’s been and how much you both have likely moved on from there. Frankly, though I’m not sure how someone can appear “wistful” in an email, I’d argue that even if he is “wistful” it may be for completely different reasons than what you’re seeing in it. If you had an affair with the guy, it was presumably because there was chemistry between you two that certainly went beyond “His Tab A fits well in my Slot B”, and it’s entirely possible that he’s “wistful” not for the chance to see you naked again, but for the loss of that friendship/connection you had. I have a couple of exes who were honestly my best friends and confidantes even before I dated them, and though I keep in touch with them from time to time, there’s a distance between us. And, yes, such is the cost of doing business many times when relationships end, but when I talk to them I do feel some regret that we’re just never going to be that friendly/close again. It may well be the same situation here.

      2. artsygirl says:

        Ouch – didn’t realize that would go over so badly. When you speak with the HR department it confidential so it would not become inter office gossip. I know for my job I HAD to disclose any entanglements/connections with other members on the staff which included previous relationships with superiors, members of the board, etc.

      3. I’m surprised this is getting so many thumbs down..I wonder where you all work. For offices with over 15 people on staff it’s pretty much standard HR policy to *require* full disclosure of previous relationships with other staff members, bosses, members of the board, basically anyone attached to the company at all. It has all to do with the company covering their ass in terms of legal situations. And in the best of worlds, yes it is all supposed to be confidential.

      4. i agree- im sure that she could actually face some sort of problems if this surfaces and HR didnt know about it…

      5. Unfortunately my co-workers have told “confidential” information to HR – and then their supervisors were notified about it before they could even walk back to their office. I have to imagine that HR sucks that bad elsewhere too.

      6. Agreed, Budjer. The HR at my place is like Project Runway- a bunch of snide bitches and you never know who’s in, who’s out, or why; but it feels very much like the people in charge are forgetting what’s really important in the world.

  3. Not the right job to take, even if it were in your own town.

    1. I agree! No way to turn this into a win-win scenario.
      You know that the guy had a hard time letting go of your brief fling for years and you were unable to maintain a friendship with him because of it. Is this opportunity so incredible, your relationship so secure, your skin so thick that you would risk, at minimum, daily “atmosphere” or at worst, pleas for the return of your sexual favors, at the hands of the person who will be conducting your performance reviews? It would be madness!!

      1. 6napkinburger says:

        Which is exactly why she needs to tell HR. If the office is a reasonably big office, she needs to tell hr that, while she feels ridiculous, she wants to make sure she starts off her job on the right foot, and for it to be ON the record. Confidential, but on the record. It should just go into a file and never come up again unless something bad happens. If, lets say, all is well until one night he, asks for a back massage and then suggests that they do something (i’ve heard this is possible), and she says no, because she’s not that kind of girl, and then her next performance review is markedly different, she isn’t saying, its discrimination, oh and btw we had sex 9 years ago and thats why… she has a documented case and HR will have no choice but to take her grievance seriously.

        But definetly don’t just *not* take the job because of the boss. Bosses get promoted, bosses change. If he is so uncomfortable working with you, he might transfer himself, relieving the problem (as if he transferred you, that’d be discrimination). Not your problem.

        Also, consider that he might not be holding a torch at all and his weirdness can be attributed to him being scared that you’re going to tell his wife — hence keeping on good terms with you, checking in, etc. Not that you are arrogant for thinking that he is, totally plausible, but it may be a non-issue.

      2. does the LW have a right to be unmolested at her new job? yes she does. is she responsible for her former fling’s behavior? no she isn’t. can she predict what he’s going to do? no she can’t. can he make things super uncomfortable for her? yes he can, quite easily.
        why would any woman of sense put herself in such a terrible position?

      3. 6napkinburger says:

        Because her “sense” tells her that she can and should refuse to let a (somewhat ill advised) relationship 9 years ago affect her current career prospects. People can act like professionals. And people can act like jerks. Even illegal jerks. Assuming that its a big company and has official sexual harrasment policies, especially good ones if it is big and public enough, she can protect herself by doing everything by the book. Wait til you’ve started, alert someone midlevel at HR so they don’t have to ask a superior and so they aren’t buddy-buddy with management to your past relationship, record (and report) any incidents of sexual discrimination (or harassment) if they occur and make the system work for you.

        If women with “sense” always just chose to avoid instead of embrace/confront tough issues (depending on the necessities of the situation), then we’d all still be secretaries bringing the menfolk coffee. I’m not telling her to be a martyr and to do this out of feminism — I’m telling to do this for her career and her life and herself.

        If women have to avoid all career circumstances that involve people we boned almost decades earlier, rightfully unaware that our paths would ever cross again, then that sounds… unpalatable to me. She did nothing wrong, he did nothing wrong so far (in terms of work appropriateness, i’m sure his wife would disagree), be adults until and unless he does something to mess with that. Then go to HR and cover your ass with a tarp the size of the eastern seaboard that felt the earthquake yesterday. Yes she shouldn’t have to and it might be easier to avoid the whole situation but it depends on how good this job is. This dream job may just be a stepping stone for her next prospect. She’s not joining a union and setting herself up for life; its corporate america and either her or her boss will be gone within 4 years, tops. She was exercising her sexual, womanly freedom when she took up with him a decade ago, and she should exercise her career-minded womanly freedom now. If he’s uncomfortable, he can leave. if he tries to make her life miserable, she goes to the head of hr, reminds them that they hired her independent of this Boss and that HE is out of line. Use the system to your advantage when you’re in the right — and most corporate places don’t put up with overt discrimination, even if only to prevent a lawsuit. and the more she does everything by the book and on the record, the more they will help her, because if not, they will actually have to litigate the lawsuit, which is way more expensive than any contribution Boss-dude had to contribute.

        On that note: Women! Do everything on the record. if crap goes down, follow the sexual harassment/discrimination guidlelines. Read the handbook. Report it. Report it each time. Keep your own record, and then report all of those. The law only protects you if you follow the corporate policy, and they ignore you or if they retaliate. Never report anything “off the record” or “unofficially”. It doesn’t count as reporting it. Never report something, but tell them “not to do anything about it just yet”. It doesn’t count as reporting it. Most companies that get away with bad treatment do so because people don’t report things because they are embarrassed or scared, or they wait too long to take action. so don’t wait — report.

  4. parton_doll says:

    Wendy, sometimes I am simply taken aback at how astute and thorough your answers are to letter writers. There are just some tough situations that I have no clue what I would say and I appreciate the effort you make to really impact someone as opposed to giving a response to grab more web clicks. Thank you for this response. I know it had to have taken a lot of time and effort on your part. Letters and responses like these are why I remain a faithful fan of this site.

  5. This is completely off topic, but Wendy, what happened to your personal blog on citywendy.com? Are you not using that anymore? I enjoyed reading it…

    1. LolaBeans says:

      i was wondering the same thing!!

  6. I agree with Wendy, especially the part about making this known to your current boyfriend. I think that’s important for a lot of reasons.

    “If I am offered this job, is it reasonable to think that he can put any old feelings aside so that we can work together?”

    Of course, it’s reasonable to think he can, but that doesn’t automatically mean he will. You also need to think about his personality and all of the ways he acted during and after your affair to determine if you think this might be something that is going to be the “elephant in the room” every time that you’re together. Nine years ago is a long time for an affair that was only a few encounters, so if you even get a suspicion that he hasn’t gotten over you, seeing you every day is going to be very tough on him. How that translates into the effect on you is going to be a factor of his personality and the nature of your interactions together than you can expect to have in that job.

  7. Great advice, Wendy.

    I can’t help but read into that fact that this guy is so fine with the LW being there….it either means he has moved on….or that he is definitely holding the torch. IF I was this VP(!) I would feel uncomfortable with this situation if in the 9 years since the affair I had become more invested in my family. Having the LW working with me would mean that information from the past affair could re-surface and cause me marital problems in the present…I cringe at the thought of the first company picnic with family.

    1. TheOtherMe says:

      “I cringe at the thought of the first company picnic with family.”


      This was a tough one & Wendy nailed it. Sometimes the LW seems so “together” that I’m confident that there will be a positive outcome to their issue. This is one of these cases. I agree that if she includes her boyfriend in her decision, it will prevent so much agony in the future.

      Good luck LW !

  8. LW, don’t overestimate your own power here. Yes, you ended things and yes, it may have been difficult, but chances are this guy has moved on and is perfectly able to function professionally with you. Nine years is a long time.

    As someone who has been on the “losing” end of some breakups, I think the guys that have hurt me (or ended things but didn’t hurt me!) think that they broke me or wounded me very deeply …when in reality, I’m pretty much fine, especially after the initial pain wears off. People change and move on. He’s not the same guy you knew, in the same way you’re not the same girl.

  9. AndreaMarie says:

    You really need to sit down and think about this. You’re right, the dynamic and relationship between you can your boss is vital. I can speak from experience (which I am not proud of). I was having an affair for about a year with a married man who worked in the same industry as I do. Eventually he offered me a job at the firm he was working at. The position was amazing and the money was significantly more than I was making. So I took the position. Worst desicion I could have ever made. As I tried to pull away from the relationship he would cause stress for me at work. Fighting with me over office IM…taking me off of certain projects, etc. I felt damned if I do damned if I don’t. If I stopped the affair he would retaliate but if I continued and it got out I would lose all the respect of my colleagues.

    Please really think this through. Best of luck.

    1. I see your point, but it sounds like you were still carrying on the affair when you started working with him…she has been out of this guy’s life for at least 8 years.

      1. AndreaMarie says:

        I was and that was my issue. I was kind of trapped once i started working there. If I tried to end the affair he would get crazy…I know it’s different since she hasn’t had any relationship with him in quite some time. But just the nature of his position gives him some level of control. Whose to say he won’t try and use his position against her if he still holds some feelings for her? Ehhh it’s a tough call for LW.

  10. Well, hey, at least you know you’ll get the job, amirite?


      You guys are no fun.

      1. silver_dragon_girl says:

        Ha, isn’t there an Internet Rule that anything ending in “amirite?” is automatically understood to be a joke? Should be…

      2. TheOtherMe says:


      3. Jenna, if it makes you feel better, I’m the LW and I totally cracked up!

    2. My jokes get “thumbs downed” a lot too, so I will help you out. haha.

  11. lemongrass says:

    Not to be snarky but I do wonder if the guy really is still into the LW or if it is her ego talking. We really have no way to know for sure and it doesn’t seem like she does either. I think that after 9 years the guy would have fallen in love with someone else during that time, be it his wife or another lady.

    1. Exactly what I was thinking! How do you pick up on hidden tones in an e-mail? You can only read them how you think they should be read, which in many cases is much different than how the writer intended.

    2. Agreed. Good point. But I think she is drawing that assumption based on how hard it was for him to interact with her in any other way while the LW was trying to break it off in the past rather than because of her potential ego.

  12. Natasia Rose says:

    This economy is so tough that turning the job down because of an affair 9 years ago would really suck. However, it DOES sound like the married guy is still into the LW. Maybe once the LW becomes an everyday reality instead of a fantasy it will actually help him to move on instead of making it worse. Either way, good luck!

  13. I think it would be a big mistake to take this job. It is one thing to work at the same office as a person with whom you’ve had a past affair, quite another for that person to be your boss. Every job assignment, performance review, and salary increase that doesn’t go the way you want will be viewed through the prism of retribution for ending or not restarting the affair. If other employees somehow learn of this past affair, every positive assignment or reward that you receive will be jealousy viewed through the lens of undue favoritism because of this past affair. Most companies would never allow you to work for a boss with whom you’ve had a prior affair. They’d hire you, but keep you in separate managerial chains. Ethically you have to tell HR. It likely is cause for dismissal if you don’t and they later find out.

    Why would you want to have this person as a boss. Putting aside the moral aspect of cheating on his wife with you, he seems to have not handled the end of the affair well, although I guess the phrase ‘minor meltdown’ may just be hype. He likely will look for future affairs and your door may well be one of the first he knocks on. That will be very awkward, when you find that he has the power to damage your career. The negatives just seem way too big to go ahead with this.

    1. AndreaMarie says:

      Exactly!! Everything negative against you in the workplace whether it be taken off an assignment or not getting a raise can be percieved as him retaliating against you because of your unwillingness to continue the affair. And worse, if word gets out that you have had a relationship..no matter how long ago…people will view all positive things towards you has favoritism because you at one point “slept with the boss”.

  14. Wow, thanks so much Wendy and to all the commenters! I was nervous about putting my dilemma out here for your feedback but I am glad I did!

    I didn’t want to make my question any longer but to address some of your questions:

    I have not told my current boyfriend yet but I am in complete agreement with Wendy and all of you on that point. I plan to tell him if I am selected for the next round and that would be a fundamental part of my decision, of course.

    The first interview was by phone and he was not involved (there is a hiring committee that does the first round interviews). But I would meet with him in person before accepting the job –absolutely. If I am selected as a finalist, I will fly out there to see the office, co-workers, boss, and HIS bosses. So I agree that the in-person stuff will tell me a lot.

    As for the wistful tone in the email, he referenced how much he had always enjoyed our talks, our intellectual connection, etc. But I’m happy if its just my ego! I very much hope he’s moved on and I would love nothing more than to put water under the bridge and to take that connection and turn it into a great working relationship. One commenter said that seeing me every day might normalize things.

    It never occurred to me that he’d expect to revive our very old affair. For starters, I’ve told him I am in a relationship. I don’t really see this as the problem. I just worry about the things that some of you mentioned –awkwardness, etc.

    I hadn’t thought of the HR angle. I need to think on that some more.

    Of course I may not even get this job but I am SO glad I asked you guys today because if the offer does come in, I want to have all of these things in mind so I don’t make such a critical decision under the gun.

    1. TheOtherMe says:

      Again LW, you really seem to have it together, I am 100% confident you will make the right decision.

      1. Awwh, that means a ton to me! Thanks for saying so. When I found out about this last week, I felt so burned –like this way pay-back for the sin I’d committed 9 years ago. But now I’m lifting my head up and trying to make a clear-headed decision.

      2. Yeah seriously. You seem so put together about everything.
        …what’s wrong with you? 🙂 teasing.

    2. Thanks for the additional comment, LW.

      As far as the HR angle – do not share it with them. Do not share it with anyone at the company because it’s not any of their business to know. Office gossip is worse than high school gossip, and you’re putting not only your job and reputation, but his job, reputation and his marriage in possible jeopardy. Out of respect for what you had with him nine years ago and a desire to keep your work life professional, leave it in the past. If you are comfortable enough to accept the offer, that should be the end of this concern.

      1. TheOtherMe says:

        I completely agree with you, PFG.

      2. I agree too. Its not like the LW just had a relationship with this man one time, she had an affair with a married man. And who knows, the head of HR could be his wife’s best friend. Then confidentiality goes out the window.

      3. when you report something to HR, it is not office gossip unless you have the worst HR department in history.

        i disagree. this really could come back to bite her, and if she has a record of it, as someone said before, and she gets a bad performance review after resisting his sexual advances, she has proof of why he has suddenly changed his tone.

      4. Even if no one outside of HR ever mentions it, it could also lead to scrutiny about his positive reports of her performance, too. If he’s suggested a bonus, good raise, promotion, etc., HR might perceive that they’ve started their affair back up, or that he’s not objective about her performance because of their past. What if they decide that he was biased in hiring her, and she’s fired by HR because they don’t want the perceived drama?

        And seriously – it’s still “he said/she said” about the past affair anyway, so it’s not as if there’s “proof”, as you claim. If she goes in to talk about an affair that started almost a decade ago, HR is going to question her motives anyway. There’s no upside and too much downside.

      5. that is all true and could definitely happen, but i really dont see more downsides to upsides. i feel like if this is indeed the LW’s dream job, she should do everything she can to protect it.

        i think this is similar to her having to tell her boyfriend about this- if you get it out in the open, on the record first, you can avoid the bad things that will happen if it comes out in other, much worse ways. honestly, depending on the way her office works, she could be fired for NOT providing this information… it is just something that needs to be very seriously taken into consideration.

    3. Yes, thanks for the update. I’m sure you’ll come to a good decision.

    4. Anonymous says:

      People who cheat don’t usually cheat with only one person so I’d read his “wistful” tone as keeping a door open personally. My dad was a sleaze and every woman he was ever with thought she was secretly ~his world~ because charismatic people do that.

      I think it is cruel to work together without the knowledge and consent of his wife but given how you know him I doubt that is a priority to you.

  15. When the LW talks to the boyfriend, it might not be a good idea to bring up the idea that she tried to maintain a friendship after the affair. Personally, that would set off a huge, clanging warning bell with me in terms of the LW and boundaries. It is one thing to be friendly with an ex, but this was a guy who cheated on his wife with the LW. The bf might think that the LW was minimizing the wrong she and affair guy did by trying to maintain a friendship, even if she eventually broke off contact. LW isn’t saying, “I made a huge mistake and cut off all ties with the slimy guy when I realized the gravity of my error.” It sounds like she is rationalizing the contact, like, well we have a lovely friendship. Lady, the guy you had an affair with should not be your friend.

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