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Can an Affair With The Boss Ever Work? What Happens When You Have an Affair with Your Boss: A Down-to-Earth Guide

Editorial Team | On October 5, 2009

Updated on 15 July, 2023

Like him or not, David Letterman’s confession that he has slept with various women who work for him 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.

Handling Personal Relationships at Work

Navigating relationships at work can be a real minefield, and when you throw an affair with your boss into the mix, things get even more complicated. Workplace romance statistics reveal that more than 60% of adults have been involved in a workplace romance at some point, so you’re not alone in this. But it’s a situation that can go either way – it could turn out to be a good thing, or you might run into some serious problems.

You’ll have to think about a bunch of stuff like how power is distributed in your relationship because your boss is, well, your boss.

You’ll also have to consider the possibility of people thinking you’re getting special treatment just because you’re seeing the boss. And don’t forget about what could happen if things don’t end well.

Plus, you have to remember that your affair could affect how you interact with your coworkers. Your relationship with your boss might change the way they see you or how willing they are to work with you. It’s a tricky situation, but with some careful thinking and planning, you can navigate it.

Spotting the Hazards: Job Challenges You Could Face

You’ve got to be clear about the potential problems when you’re thinking about having an affair with your boss. People might start thinking you’re being favored, which could mess up the vibe in your team. If things end badly, it could make things pretty uncomfortable at work and might even put your job at risk. It’s not just about your current job either – it could also affect how others in your field view you, and impact your future job prospects.

Power Play: A Closer Look at Affairs with the Boss

When you’re having an affair with your boss, there’s a power game at play, and that can make things messy. Your boss plays a big role in how your career goes, and that could affect your personal relationship.

This imbalance of power could lead to situations where you feel pressured, and that’s not great for your job or your personal life. This stress could make it tough for you to do your best at work and might affect how much you enjoy your job.

Company Rules and Repercussions: What Your Workplace Says About Affairs

Before jumping into an affair with your boss, it’s really important to understand what your company’s stance is on workplace relationships. Some companies might have strict rules against it, while others may be cool with it as long as you’re honest and open about it. Ignoring these rules, though, could lead to some serious problems, including losing your job or even facing legal issues.

This is because while not all workplace romances end up in disaster, when they do, it can create problems not just for you, but also for your employer. It can stir up drama, create awkwardness, and even lead to productivity issues. Plus, let’s not forget about the fact that breaking these rules might also change how your coworkers view you.

They might start seeing you differently or might feel that you’re getting special treatment. So, before you decide to go ahead with your affair, make sure you know exactly what you’re getting into and what the potential consequences might be.

Keeping it Professional: Balancing Work and Personal Life

If you’re having an affair with your boss, you’ve got to know how to keep your personal and professional life separate. It’s important to stay professional at work, no matter what’s going on personally. Set clear boundaries so your personal life doesn’t start messing with your work. This might be tough to do, but it’s crucial for handling an affair at work.

Lessons from Experience: What Others Have Learnt From Workplace Affairs

Stories from people who’ve had an affair with their boss can teach you a lot. They give you a peek into what challenges you might face and how to deal with them. These stories can be helpful, but remember, your experience might not be the same as theirs.

Conclusion: Thinking it Through

Choosing to have an affair with your boss is a big decision and one that needs a lot of thought. Make sure you consider all the ways it could affect your job and your personal life. Every situation is unique, and just because something worked out (or didn’t) for someone else, doesn’t mean it’ll be the same for you. Always keep your well-being and career in mind when making this kind of decision.

FAQs: Understanding the Realities of an Affair with Your Boss

1. What problems might I run into?

If you start seeing your boss, a few things might go wrong.

First, people at work might think you’re getting special treatment. This could be anything from easier work to better projects. Even if this isn’t happening, just the talk could make work a lot less fun.

Next, there’s the issue of who’s in charge. When your boss is also your partner, it can mix up your work and personal life. This can make things really confusing and stressful. It’s hard to know where work ends and your personal life begins, and this could cause arguments or make it hard to focus on your job.

Lastly, if things end badly with your boss, it could make work really difficult. You might feel like you need to leave your job or your boss might treat you differently. This could lead to problems with your work, like missed promotions or even losing your job. Plus, it could make every day at work awkward and uncomfortable.

2. How might my coworkers feel if they find out?

If your coworkers find out about your affair, they might not take it well. They might start to feel upset or annoyed if they believe you’re getting the easy ride because you’re seeing the boss. This could change the way they interact with you, maybe they’ll be less friendly or less willing to help out in team projects.

The best way to handle this is to keep it professional when you’re at work. You need to show that your personal life isn’t affecting your job. This means not letting your relationship with your boss change how you do your job or how you treat others at work. It’s about drawing a line and keeping your work life and personal life separate. But remember, even with the best intentions, people might still feel upset.

3. What does ‘power play’ mean when having an affair with a boss?

‘Power play’ in this case means that your boss, because they’re your boss, naturally has more control or power in your relationship. They’re the one who’s in charge at work, right? This could end up making you feel stressed or under pressure, not just at work but also in your personal life.

For instance, you might feel like you always have to please them or that you can’t say no to them, even when you’re off work. This could mess up both your work and your personal life, making it hard to relax or feel comfortable. It’s like you’re always at work, even when you’re not.

4. How might my company’s rules affect my decision to have an affair with my boss?

Your company’s rules could play a big part in your decision to have an affair with your boss. Every company has different rules about dating in the workplace. Some companies don’t allow it at all, while others are okay with it as long as you’re honest and open about it.

If your company is against it and you decide to go ahead with the affair, you could end up in hot water. Worst case scenario, you might lose your job. Or if you’re trying to keep the affair a secret and people find out, that could also lead to trouble. There might even be legal problems if your company decides to take action. So, before making any decisions, it’s really important to know and understand what your company’s rules are.

5. How do I keep my personal life and work life separate when having an affair with my boss?

Keeping your personal life separate from work can be tough when you’re seeing your boss. You need to make sure there’s a clear line between what happens at work and what happens outside of it. You gotta stay professional when you’re at work. This means not letting your relationship get in the way of doing your job.

You also need to avoid situations that might be uncomfortable. For example, you shouldn’t discuss personal matters during work hours or at the workplace. You also have to make sure not to show any favoritism or act differently at work just because you’re seeing your boss. It’s all about balance and not letting one part of your life mess up the other.

6. Could I face legal issues?

Yes, it’s possible that you could run into some legal trouble. This really depends on your company’s rules and the laws in your area. If your company has strict rules against office affairs, or if people believe your boss is giving you special treatment, there might be some legal consequences.

Worse case, if your affair with your boss turns sour and it becomes a case of harassment, that’s a serious legal issue. If you’re not sure about all this legal stuff, it’s always a good idea to talk to a lawyer. They can explain everything to you and help you understand what risks you might be taking.

7. How can I stay professional at work when having an affair with my boss?

Staying professional at work when you’re seeing your boss means you have to be careful about a few things. First, you have to respect boundaries. This means understanding that work is for work, not for personal stuff.

You also need to make sure that your relationship with your boss doesn’t change how you do your job or how you treat your coworkers. It’s really important that you’re fair to everyone at work. Don’t let what’s going on in your personal life affect your behavior at work.

For example, don’t let your boss give you easy work because you’re dating. And don’t be mean or unfair to your coworkers because of your relationship. You have to treat everyone the same way you would if you weren’t seeing your boss. It’s all about keeping things fair and balanced.

8. Could an affair with my boss affect my future job chances?

Yes, having an affair with your boss could definitely affect your chances of getting a job in the future. If people at work or in your industry hear about your affair and see it in a negative light, it could harm your reputation.

And let’s face it, when you’re looking for a job, your reputation matters. Potential employers might hear about your affair and worry about possible issues in their own workplace. Or they might just see you as unprofessional. Either way, it could make it harder for you to land a new job or move up in your career.

9. How could others’ experiences help me navigate an affair with my boss?

Listening to other people’s stories can be really helpful if you’re thinking about having an affair with your boss. They can give you a heads up about the kind of issues you might run into and how they handled them.

This could be anything from how they managed to keep things professional at work, to how they dealt with rumors, or even how they handled a bad breakup.

But remember, just because something worked or didn’t work for someone else, doesn’t mean it’ll be the same for you. Your situation is unique, so while it’s good to learn from others, you’ll also need to think about what’s best for you and your specific circumstances.

10. What should I think about before deciding to have an affair with my boss?

Before deciding to start seeing your boss, there’s a bunch of stuff you need to think about.

First, you have to think about what could go wrong. This could be anything from getting treated differently at work to feeling under pressure all the time.

Next, you need to know what your company’s rules are. Are they okay with office relationships? What happens if you break these rules?

You also have to think about your coworkers. How will they feel if they find out? Will it change how they see you or treat you?

Legal issues are another thing to consider. Could you get into trouble if people think your boss is favoring you because you’re seeing each other?

Another big thing to think about is how this could affect your career. Will it help you move up or could it hurt your chances of getting a good job in the future?

You also have to think about how you’re going to keep things professional at work. How will you keep your personal life separate from your work life?

Last but not least, you need to think about whether this decision matches up with your personal values and goals. Is this something you really want to do or are you just getting caught up in the moment? Taking the time to think about all these things can help you make a decision that you’re comfortable with.

Check out other articles by best-selling authors:

Dawn Rasmussen – Top Five Questions About Resumes Answered

Sunny Lurie – Eight Proven Strategies to Open the Door to a Vibrant New Career

Stacia Pierce – How to Search for a Job During the Holidays

Dawn Quesnel- Helpful Hints for Job Seekers

Stacia Pierce – Conceit vs. Confidence


  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. B.tru

    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…..

  23. Hazeena

    I have experienced this myself with my ex-boss at work! We had an affair, when his family was away from him. We both knew this would never work, and hence moved on!

  24. M

    A legitimate relationship and an extra-marital affair are two very different things that I feel some of those commenting have confused here. Of course cheating is not okay… duh. That said, I caved and ended up in an intimate relationship with my boss (I am his PA) but it took SIX YEARS for him to win me over and in that time we had become very close friends. We have been together for a year now and our colleagues still do not know. Given that he has a child and I don’t date, this was not a decision either of us took lightly but I am looking forward to our future together. It really depends all on personal circumstances and comes down to the individuals themselves. It’s also a different situation because this happened in a small director-run business without HR or middle management.

    It’s possible that starting a relationship in the workplace has a higher chance of success as after getting to know each other for years, the relationship already has a strong foundation of friendship and trust… I suspect it is much harder to find that on tinder 😉

  25. Rich

    My wife and I had three children all girls, ages 3,5,13. I was in the hospital after a serious motorcycle accident. My wife came to hospital and told me she didn’t love me anymore and prayed for me to die and wanted a divorce. I found out that she was having an affair with her Boss. Due to their affair the married Boss was caught and the wife filed for divorce. The Boss and my wife were both high level Government employees. The Boss for fearing of losing his job had the divorce papers sealed. My wife left me and the children and moved in in with her Boss. After several years the Boss booted her butt out and told her not to come back. My children were mentally affected by the divorce and hated said Boss. The ex-wife still made them to go with her to Bosses home to stay the weekend. My ex-wife told told her friends that didn’t status or money being Police Officer.

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