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March 22, 2023

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Can an Affair With The Boss Ever Work?

  • On October 5, 2009

Like him or not, David Letterman’s confession that he has slept with various women who work for him on CBS’ Late Show has prompted a flood of water cooler chatter.
It is also raising questions about when – if ever – is it appropriate for the boss to have sex with an employee.
We’ve heard from some of you who say your marriage has been ruined by women cooing to your husband — who just so happens to be the boss. But others have written in to say they met their life partner on the job and have been together happily ever since.
It cuts all ways, but this much is true: workplace romances are very common today. In a recent CareerBuilder poll of more than 8,000 people, 40% owned up to an office romance. A survey revealed that even more people – 58% — see romance as a fringe benefit of their job.
Do we spend so much time at work these days that it’s bound to happen? Is Letterman’s behavior the same as what the guys on the hit 60s drama Mad Men engage in regularly: taking advantage of “defenseless” women in a boy’s club atmosphere? Or with more women in positions of responsibility in the workplace, including in Letterman’s shop, have office romances advanced beyond that in the last half century so that the line between right and wrong is more nuanced and blurred?
Let us know what you think: Can an affair between a boss and a direct report ever be truly consensual, or does that power structure make it impossible? Is it possible to change a culture that accepts office flings as a given – or should we not be bothered by what happens among peers?


  1. MWA

    After losing my job in January 2009, I have been unable to find a new position. I haven’t even been called for an interview, even after sending out hundreds of resumes. I signed up with Workforce One for help finding a job. They still have not sent me on an interview.
    Therefore, it is highly unlikely I will be having an affair with anyone at the work place.
    I wonder if I sleep with the guys at Workforce One, maybe then I can get an interview.

  2. Arnie

    With higher levels of equality in the work place (especially in cities like New York, etc.) and the long hours spent together which reduce the other possibilities of socializing, workplace romances are more common and excepted as the norm. Even between boss and worker you will find the worker going after the boss without the fear of reprisals from the boss because the mechanisms in law to fight back places power in that workers hands. The old rules still hold true however. It is NEVER right to go after those who are in relationships and those in such relationships still shouldn’t try to have the adventure of having something on the side. With that said, throw people together for long peiods of time who share a common interest and work battles you set the stage for such things to happen. This is natural for us humans and it does take a great deal of vigilance and personal moral strength to fight such entanglements under those conditions but it is worth it for everyones sake. It can be like swimming upstream and it’s getting harder. It’s a sign of the times and not such a good one.

  3. T.G

    It may not be common but I think it can. I also think it depends on the industry, type of job and personalities of the people involved. Why personalities? If you are a hound always looking for a bone or a cat on a hot tin roof well, the office affair is just what it is-an affair. Nothing more nothing less. Let’s face it flings happen all the time and unfortunately it may be with the boss and a subordinate. If it’s not consenual it’s sexual harrassment and/or abuse of authority. I believe the two feel completely different. With all the sensationalism we see on TV about office love, a romance with your boss these days are welcomed and embraced. How does that affect the workplace? I’m sure there are pros and cons (I’ll venture to say the cons out weigh the positives). But a true ongoing love affair between mature people is something different,rare, and it does not cause the same problems or hazards that an office fling does. Usually both parties have an interest in making sure the workplace doesn’t become a circus all about them. But again industry, job, position and personalities play an important part. Just think First Lady Michelle and President Obama’s romance started on the job. I bet she’s glad she overlooked a few things to find the love of her life and he too.

  4. The only real issue is power. When you are the boss, you have more power than your employee. Its innate in the position. When a boss has a sexual relationship with an employee there is an imbalance of power. Its inherent in the employee/employer relationship. As a result there is no way the relationship can be balanced an equal. The boss’s position prevents the equal foundation necessary for a healthy interpersonal connection. It’s why ministers, teachers, and parents can’t have sex with their congregants, students and children. Its not an equal relationship. The employee, congregant, student and child are all in a lessor power position and cannot get their needs met equally.

  5. JA

    I think that high level employees can have an affair with their boss that is truly consensual because someone at that level understands the potential consequence of their action and probably is not participating to advance their career. I think an overall renewed commitment to marriage/partners needs to happen throughout this country, however I don’t believe the personal interactions of co-workers is anyone’s business as long as it doesn’t impact their performance on the job.

  6. Becky Smallwood-White

    I can’t even believe that these questions are being asked!!!! If the boss and the woman in the office are both separately married, then NO!! How many families have to be destroyed over taking a poll? It is WRONG and ALWAYS will be!!!! Please DON’T encourage women to have an affair with a married boss!!!!!!!!!!!!!!!!!!!!!!!!

  7. vanessa

    i think that for the most part it is consensual everyone has their own decisions to make so take responsibility for them. The women could easily said no.

  8. JT

    An affair is an Affair, it’s just wrong no matter where it happens.

  9. Kay

    Unfortuntately this is quite common and my Husband the VP of IT in a fotune 500 company was terminated in 2007 for crossing that very line. Employees noticed that a particular woman was clearly receiving opportunities that she was not entitled to, and therefore an investigation was launched and so was he.

  10. Laura

    The glass ceiling is still firmly in place! Powerful men, by definition, can not put that aside and rule out the chemestry that occurs when projects, money and world commerce are affected by their very wim….The women who are attracted to this, also by definition, are climbing the ladder literally…..I am so glad I am no longer in the game!

  11. Martha

    It still takes 2 to tango. As I understand Letterman was not married at the time. But who cares. Many a woman has worked her way to the top on her back. As my sister’s husband told me…let’s keep it in the FAMILY. He was rich and powerful. His Daddy did it in his time and Sonny followed in his Daddy’s footsteps!!!! The answer is YES or NO. Morals of a skunk…you betcha!!!!

  12. WLF

    All too often a ‘slippery slope’. Who gets hurt? The spouse(s) – Significanot other(s) – Children, etc.. Is the risk truly worth it in terms of your professional career (reputation, job retention, job advancement, etc)? What about damage to your own self-image? Regrets, recriminations, etc..
    What price dalliance, given all else at stake?

  13. Goldenintl

    During an interview, in which I was highly qualified for, I had instant chemistry with the hiring manager, who later became my boss and the two weeks before my first day on the job, we started a relationship. However, when he began acting extremely obsessive, I decided it wasn’t a good idea and tried to end it, the situation turned very sour and I was mistreated beyond belief. In the end HR stepped in and terminated him. I was shocked and thought I was going to get my walking papers, especially since he had been with the firm for many years, but in a professional corporate world there is behavior called non tolerance and HR will do whatever necessary to avoid potential lawsuits. Their policy being, if you’re in a role managing others, you are responsible to set the appropriate example. I would not recommend anyone in a supervisor or high level management role to become romantically involved with an employee. I was given legal advice to sue, but I loved my job and just wanted to be treated fairly, however, I’ve known others who wanted pay backs and a big pay check, either way, nobody wins.

  14. Jan McQuarrie

    Having an affair with a married man is always tricky–moreso when he’s your boss. For starters–he may claim that he’s married in name only; however reality states that he may not leave his wife. As Goldenintl stated, there is the potential of a law suit–the possibility of being fired and jeprodise your job/career/promotions. If it goes south, then the potential of a tense working situation is there. As for dating co-workers—-procede with extreme caution.

  15. You talk about two very different kinds of circumstances in your opening article. There’s a world of difference between becoming involved with someone at work and becoming involved with a boss or direct report. A relationship with a colleague or peer is less problematic and no doubt does happen more now with longer work days. But a relationship with someone who works directly for you, or to whom you directly report, is, has always been, and will always be a serious problem for both parties as well as anyone else in your organization. It’s just a bad idea and is likely end badly.

  16. JJ

    What about moral commitment! What about the vows you took before God? What about marriage do people not understand? I know we are all human and we sin however a constant reminder can take place. Go to church and worship weekly. Read Gods word daily. It is okay to do this and respectable even in this day and age. Give up a night of working late. Feel good about yourself. Get reassurance that there is always someone there watching out for you. HE strengthens you through all things!

  17. NF

    Adultery is NEVER right!

  18. lerato

    it really takes two to tango but at the same time the boss should now better as the the big guy,if one is married then that is cheating and is wrong but if not enjoy it while it last.

  19. Susan

    I never date anyone at work. Not co-workers or supervisor’s. All this new hiring for chemistry makes me uncomfortable. I think it is a little weird and inappropriate at work. I really prefer business to be business.

  20. Charlean

    I work for a fortune 500 company and my married assistant manager at work likes me. He has made sexual comments about hooking up with him. He constantly stays in my area talking to me about his wife, no.2..others have noticed the way he is with me and have mentioned him spending too much time with me so lately he’s backed off but he calls and texts my phone. I don’t want any drama or complications even though I enjoy all the attention. But it’s not worth it

  21. Kris

    The question is, can an affair with boss, works? The answer is, Yes. If both parties knows how to take care of each other’s work, reputation and the secret affair.

  22. These action are not normal in the old world but people think it’s ok in the new times but it’s adulty it will feel good for a little while then the new person will be like the one you’re with now trust me it’s fun for little while very little while…..

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