I’m Afraid I’ll Cross a Line With My Boss!

A question to Ask the Workplace Doctors about
how to get over an attraction for the man who is her boss.

I caught myself staring at my boss and I was smiling about it. Instantly I told myself to stop. He’s married, but not only that, he’s my boss. He’s such a nice man. I’m not exactly sure on the age difference. However he’s one of the youngest bosses I’ve had. I would say he’s in his 20’s possibly he’s 30’s. I myself am in my 20’s. I had one previous relationship with a man I used to work with. But the moment he became a manager, and my supervisor, we put things off. He was offered a transfer to a different location and after that we did date. It was different that time, because he was single.

My current boss, who I believe I’m attracted to, is married. Not only that but his wife and him went through the pain of having a stillborn together. Ever since I began catching myself staring at him, thinking about him, and after finding out what he went through; I make sure I always ask him if there’s anything I can do for him or anything he needs me to get done before I leave. I know the way I feel is completely wrong for multiple reasons. I fear that one day I may cross a line that I hope I will never cross. And usually it would be easier to put a man out of mind but I can’t read for sure how he is. I keep getting mixed signals but at the same time I’m not sure if it’s just in my head. We both have high ranked jobs and the last thing I would want is to cross any line with him. How do I put out of my mind, this attraction I have for him?


If you’ve seen our archives, you know that being attracted to a boss is a frequent question. Among them:

Want to Get Over Loving My Boss

Attracted to My Manager

Romantic Feelings for Boss

Attracted to Boss

Feelings For My Boss

In Love With My Boss

How To End An Affair At Work

What Should I Do About Feelings for My Boss?

When two people work together there often is a feeling of closeness and intimacy. Work colleagues share experiences that spouses or partners do not have. In addition, both men and women are dressed and groomed attractively and, especially at the executive level, they usually show their most polished behavior to the people they want to keep as allies. It isn’t surprising that people become attracted in emotional ways in those situations. The dynamic of having an attractive boss is also part of it. If he was the custodian or mail room clerk, you probably would not feel the same way. All you have to do is read a romance novel about the subject, to realize the fantasies that can be built around it.

I don’t think your goal should be to get over being attracted to your boss. You will probably always find him attractive and will maybe always have a little inward sigh for what might have been if things had been different. But, you need to accept that he is a nice man who is attractive, but unfortunately, off-limits in every way. Once you just say it and move on, you will be able to submerge your feelings and redirect them–and one day it won’t be so difficult to do.

One way to accept the reality of the situation is to consider what you think the outcome would be if he told you he is attracted to you and you could tell him the same thing. Do you think no one would ever notice the new connection? You can bet they would, because they always do. Always! Could you both stay in that job? I don’t think so, because I don’t know of a company that would accept an open affair between a married boss and a subordinate. Would he leave his wife to be with you? I doubt it. But, if he did, would you be transferred to another work area or would he be transferred, so the two of you could be married and not have a work conflict? I don’t think that would happen either.

So, the best you can hope for, if you cross that line, is to tell each other that you’re attracted, maybe grab a kiss now and then, maybe go someplace and have sex, and then what? It would be unpleasant, unromantic and make him just another guy who is unfaithful to his wife, while making you just another woman who was part of an affair with a married man.

I mention all of that to remind you of the reality of the situation.

Here are some ways others have coped with working around someone they feel romantic about:

1. Resolve to take the high road and express your caring by protecting his life and future as much as you’re protecting yours. As the song, “The Impossible Dream” says, “To love, pure and chaste, from afar.” It isn’t easy to do, but it is possible. If you do care for him, the last thing you would want would be to ruin a young man’s career and his marriage and life. You could probably do that, if you set your mind to it—but that is not the kind of person you want to be.

2. Put your focus on the technical and administrative parts of your work and be excellent at that. Stop staring at your boss (that is one of the most common sexual harassment complaints people write to us about—their male colleagues or bosses stare at them). Stop being your boss’s Office Wife or Office Mother, just do your job very well. I know many women who are almost nauseating in their efforts to be caring and helpful for a boss who does not need it and didn’t ask for it. In fact, he may prefer you not do it, but he doesn’t know how to tell you. Courteously asking if there is work to do is one thing, but carrying that to extremes is obvious and can be a source of embarrassment.

I was in an office last year, as part of a meeting with an executive who I had thought well of until then. The executive’s secretary came in to see if we wanted coffee, then to see if he needed something, then to see if he wanted her to return some phone calls, then to see if he would like her to adjust the temperature, etc. etc. When she left the last time, we all were a bit uncomfortable at how intimate she seemed to be with him. She looked at him and talked to him, as if they were involved seriously. He said, “What can I say, she’s crazy about me. You ought to see her hanging onto my legs as I drag her out the door when I leave at night. I have to toss candy on the floor to distract her, so I can escape!”

The men laughed, but I didn’t, because I thought he should either stop her from being like that or not make fun of her behind her back—and I told him so. That most likely is not at all like you or your boss behaves. But, the very fact that you purposely interact with him in a way that says, “I’d do anything for you”, is not the best way to have a boss-employee relationship that stays comfortable for him and appropriate for you. .

3. Find things away from work that will distract you from thinking about your boss. Fitness, a hobby, having a very, very clean house, family, friends, whatever it takes. Occupy your mind with something else. One of the best things is to learn something that requires concentration to do it well. Yoga, a craft, swimming, martial arts, cooking, anything that is more than reading or watching TV.

Right now, thoughts of your boss are like a melody, stuck in your head. The only way to get rid of them is to replace them with something else. Get out of the habit of thinking of him romantically and get very busy thinking of something else.

What you do next will make a big difference in the future. You can continue to day dream about your boss and risk creating an embarrassing or punitive situation. Or, you can just focus on work and let him live his life with his wife and hopefully another baby one day. At the same time, give yourself the chance to be available for someone else—someone who is available to you and who can be completely yours.

Best wishes to you with all of this. I know it is challenging, but you know that it is doable and the best thing to do.

If you have the time and wish to do so, let us know how you are able to handle it effectively.

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.