How Can I Stop an Affair With My Boss?

Note: This was a very complex situation. We have changed and condensed the question considerably, to protect the identity of the person asking the question. However, we thought our response would be helpful to others.

Question: Several years ago, as a very young employee, I was going through some personal issues and my boss, who is twice my age, helped me work through them. The result was that we became close and have been in an affair since then. Now, however, I want to end it so I can start having a normal life with friends and people my own age. I’m also tired of juggling my schedule to have stolen moments.

He is now in the middle of a divorce, so he wants me to spend even more time with him, but always secretly. I don’t want to have a sexual relationship with him anymore, although I do love him like a dear friend. But I’m afraid I’ll lose my job if I try to break it off with him. When I’ve discussed it in the past he has made things very difficult for me at work.

I’m feeling very afraid about the future and also worried about what I will do if I lose my job. My friends tell me to get professional help, because I’m having anxiety attacks and feel like things are out of control. What should I do?

1. First, Dr. Gorden and I completely agree with your friends who suggested you talk to a professional. There are many facets to your situation and each requires careful consideration and the advice and support of someone closer to you than we can be—and someone who is professionally trained in the complexities of the life-situations in which you have been involved.  You would benefit from talking to a professional over a considerable amount of time so you can be completely open about your life and your challenges.   

Your issues with your boss/paramour, is summarized by the unhappy statement we hear very often: I wish I hadn’t started an affair with my boss. Or, I wish I hadn’t started an affair with my employee. Just last week a woman wrote and said, “Oh God, if only I could do it again, I would have stopped it in the first days we hinted around about it. At first it seemed so exciting and I felt special. Now, I hate every second of the life I’m living because of it.”

It isn’t surprising there are workplace relationships, especially between male bosses and younger female employees. Everyone is usually well-groomed, pleasant acting, and sharing work situations that bring closeness. Bosses seem to have power and status and the young women seem fresh and flatteringly interested, so each has something to attract the other. But unless the feelings mutually drift away, someone nearly always ends up hurt or offended. Rarely is there a happy ending.

But, even if that problem is resolved, you will have other mental and emotional issues that will follow you into other relationships, if you do not deal with them now.  So, you should certainly consult with someone who can help you feel better in many ways. Your health insurance will probably have coverage for such counseling. If not, check for resources at a women’s clinic or with similar centers.

2. Sexual activity between a young woman and older men does not bring psychological maturity for the woman, in fact, usually just the reverse, because of the anxiety and dependence it creates. But it does bring a sense of shrewdness and some practicality about giving something to get something.  Unfortunately, at some point it isn’t worth it—and you have reached that point.

If your boss was as in love with you as he says, he would have divorced his wife a long time ago and married you. He would not keep you a secret. He would not want to monopolize your private life. He would not make you the subject of office gossip—and you can bet there is that. He would realize that you have to do more work and planning to spend time with him, than he has to do to spend time with you. All he has to do is be there, you have to make it happen. He would be aware of the age difference and how that will affect you in the future. He would have thought about how creepy it is for the average man to be sexually involved with a girl half his age anyway. It’s even creepy for movie stars to do it!

The truth is, he’s not thinking of any of that. He wants a young sexual companion and you are already in that role, so he’s not obligated to try to find another one. That is the reality. You have demonstrated far more concern about his welfare than he has demonstrated about yours. He has the money to leave town when he wants, travel where he wants and live well. You don’t. So, he makes you dependent upon him for those things, but expects you to find excuses at work so you can keep him company.

Based on your description, your boss sounds like every older boss involved with a much younger employee. He’s not looking for a relationship with a woman his own age, he wants a young woman to impress and help, so she depends upon him. He’s not looking for a social partner in his own city, where he can proudly have her as an acknowledged companion, he wants to travel out of the area or out of the country, with an escort he knows already. He already had a business years before you came along as a brand new employee, so he doesn’t need you for significant advice about running his company. If he did, he would marry you and let it be known you are partners in the business.

All of that sounds harsh, but it needs to be said. Your boss undoubtedly enjoys your company and conversation, especially since he lives alone now. He likes your travel companionship when he’s traveling on business or on his own for pleasure, but he wants you to be convenient for him. When he was living with his wife, he had a life with her in addition to stolen times with you when it was convenient for him, whether it was convenient for you or not. In years past, a man’s mistress was called a “convenient” for that very reason.

Keep in mind that your boss will get through his upset over your break-up with him, just as you would if the situation was reversed. You will get together and break-up with several more people before you settle down with one person, if that is what you decide to do. He has probably done the same thing in the past. So, you focus on your life and let him deal with his.

You are angry with him for his lack of understanding about your situation, but much of your message made excuses for him. That isn’t good for you OR for him.

3. The blunt answer to your problems is to quit your job and get away from him. If you stay there you will not be able to concentrate on your work, he will make his unhappiness apparent, and you will have to quit anyway. Or, you could wait until he fires you, then claim unemployment compensation while you look for other work. This is not a good time to be looking for a job, but if you have knowledge and skills you will be able to find something, even if it’s not what you will end up with down the line. Only five years ago you got this job, so it is possible to find one now.

You may be able to stay, if he can adjust quickly to the change in relationship, but that remains to be seen.

*****I want to remind you of something: You have been working under a quid pro quo (THIS FOR THAT) environment. You could easily claim sexual harassment under those circumstances and cause him a great deal of problems. The threat of that might be enough to pry him loose from you. It doesn’t matter that it was consensual, the fact is that you would stop the relationship if you weren’t afraid of being fired. I don’t think you will want to do that—and I wouldn’t either, if I were you. But, he may realize it and be more amenable to the change in status than you expect.

4. Until you quit or if instead of quitting you decide to try to make it work with you staying there, change your life schedule to work for you, not him. He doesn’t know what you do or say when you’re not around him, so make up the schedule you need.

You certainly can use your mother’s health for that excuse. Tell him that your mother needs you to help her with some physical therapy she has to do every evening, so you can’t come over any evenings now. Tell him you’re taking her to an exercise class on weekends. You can say you’re attending a faith-based class on Sundays or that you’re taking some adult education class that appeals to you, like cooking or Yoga or stretching or something else.

Then, don’t answer your phone and don’t return text messages during those times. Go out with friends, date the young man you’ve met, or do other things you enjoy doing. He can be angry, but if those things were true, you would have to let him be angry.

After you’ve done that for a couple of weeks, move on to quitting the relationship. Or skip the build-up and just stop the relationship.

5. I often remind people of the Paul Simon song that says, “there must be fifty ways to leave your lover.” Millions of women and men can attest to the truth of that lyric. There is no point in giving a long and rehearsed speech, just blurt out the truth, without weak words to try to soften it. The more you try to make him feel better the less he will believe you.

If you say, “I’ll always love you in a friendship way,” he’ll only hear that you will always love him, so he can keep trying to get you back. If you say something about wanting to be fair to him, he’ll have a reason to argue and say it isn’t fair to make him unhappy. Nothing but a blunt statement will work the way you want it to work. It is also more honest than having him think you are just playing hard to get and will change your mind.

Some people think sending an email is to cruel, but I think it’s the best way. However, I can understand that many people feel they should talk face to face.

Something like, “Greg, this is hard to say, so I’ll say it and get it over with. I’m not going to be in an affair with you anymore. I’ll be a good employee at work, just like always, but I’m not going to have a relationship outside of that.” (Then stop talking and let him say whatever he’s going to say.) He will know what those few sentences mean, so you don’t need to explain that you won’t come to his apartment or meet him or travel with him, or have sex, or the other things that have been part of the affair.

After that, be a broken record if he argues about it. “There’s no point in us discussing it. I’m not going to be in an affair with you anymore. Like I said, I’ll be a good employee at work, but I don’t want to keep having a relationship outside of that.” “I’m sorry you feel that way. But, I’m not going to be in an affair with you anymore.”

Let’s say he surprises you and says he’ll marry you if that will make a difference. Just rephrase, “No, Greg, that’s not the point. I just am not going to have a relationship with you outside of work anymore.”

The good thing is that once you have said that, there is no easy way to backtrack and you’ll feel an instant load off your mind. After that, it’s just a matter of sticking to it.

A woman once told me that when she said “Mike, I’m not going to be in an affair with you anymore”, she felt a surge of power in her mind and heart that scared her, it was so real feeling. She said she had dreaded it for weeks, then said it and slept better than she had slept in a year.

She still had to deal with the awkwardness at work and his attempts to win her back, but within a month or so, she met someone else and her boss went to the back of her mind very quickly—and he could tell, so he only mentioned their previous relationship occasionally. She said it hurt her feelings a bit when she realized he really wasn’t going to grieve over her, but she moved on and so did he.

6. You mentioned several things you’re afraid of about ending the relationship. Most of them revolve around the financial part of it, understandably. Others, like damage to your car or other things, are not so likely. One thing I can assure you. If your boss creates a problem for you to such an extent that you can’t get employment or feel threatened in some way, I would bet an attorney would take your case on a contingency basis for sexual harassment and coerced sexual activity. It would be one thing if you were an ineffective employee. But, if you are a good employee and your only offense is not having sex with your boss anymore, you have a whole bunch of laws on your side.

7. Dr. Gorden suggested you write a letter to yourself about what you think is best to do in the long run. His thought was that you could do a lot of problem-solving for yourself in that way.

For example, consider answering these questions for your own consideration. They might also come in handy if you discuss this with a professional:

(1.) If you could describe your life the way you would like it to be in three months, what would it be like?
The reason this is valuable, is because I think you will find that you would like to be out from under this burden in three months….probably tomorrow. I sometimes ask people, “If you could wave a magic wand, what would you like to have happen?” Then I ask, “Does it require a magic wand for it to happen?”

(2.) What marketable skills or areas of knowledge do you have? If so, is it possible that another business somewhere in your area could use you? Do you have a network of contacts that might be useful?

(3.) Do you think it is likely you will want to work for this company for another thirty to forty years? If you might leave sometime, now is a good time.

(4.) What good things does this current situation add to your life? Are those so good you can’t give them up?

(5.) What negative things does this current situation add to your life? Is it worth some discomfort to get out of it?  Is there a chance something else will happen to get you out of it, or will it require action on your part? If it will require action on your part, are you prepared to do it? Is there any reason to delay?

There’s a saying about goals: If you don’t know what to do every day, instead of or in addition to what you are now doing, you don’t have a goal, you have a fantasy. You seem to be someone who can set goals and achieve them. Decide what you will need to do instead of what you have been doing.

You have limited available time, and time is life—your life. Why ruin your twenty’s decade this way? You can do better for yourself, even though it will be difficult. However, you have overcome other difficulties and succeeded, so this can be overcome as well. I realize that’s easier for me to say than for you to do, but you have a lot going for you and are not in a hopeless situation.

All of the above are just thoughts and things to consider. I don’t know your precise situation, but you can adapt the concepts. Focus on where you want to be, then plan on how to get there. You know the general path, but you alone can determine the details.

I do believe you will be more successful if you seek counselling from someone in your area. Work with a professional on this immediate situation, then deal with the other things that led you into it and could have an effect on your life in the future.

Best wishes to you. If you have the time and wish to do  so, let us know how you are progressing in your efforts to regain your life and your happiness.

Tina Rowe
Ask the Workplace Doctors

Tina Lewis Rowe

Tina had a thirty-three year career in law enforcement, serving with the Denver Police Department from 1969-1994 and was the Presidential United States Marshal for Colorado from 1994-2002. She provides training to law enforcement organizations and private sector groups and does conference presentations related to leadership, workplace communications and customized topics. Her style is inspirational with humor.