Should I Stay At A Job Where I Love My Boss?

A question to Ask the Workplace Doctor about
romantic feelings for the boss. 

Should I stay at a workplace where I’m deeply in love with my manager? I’ve been here for 2 years and since I first saw my manager for my first interview, I instantly fell in love.

Obviously, I got the job and have excelled in the position assisting her because I always want her to be happy and because of it will definitely lead to promotions. However, it really seriously bothers me feeling this way and doesn’t seem she’s into me that way and as she usually keeps relationships within the workplace professional as she has a kid and has a mortgage to pay all by herself.


Your decision about staying in your workplace will probably involve considering at least five key questions:
1. How difficult is it for you to keep your feelings to yourself? Most of us can conceal our dislike for someone, but it isn’t as easy to conceal our liking for someone. There are many appropriate ways to show esteem and even affection, without appearing to be romantic or excessively personal. But, the minute you ever say or do something that comes across as an effort to be romantic or personal, you won’t be able to take it back. At the least, your boss will probably never feel comfortable with you again. At the most, she might try to place some distance between you and her in the company.

Or, if she feels some attraction for you, it might open the door to having her say or do something that creates very negative results for both of you. In most companies she will be prohibited from having a relationship with you. You both might lose your jobs and that would be a terrible thing to bring on either of you. Or, she might “counseled” about it and it could cause her to lose her reputation and influence.

The lyrics of the song from the play and movie, Camelot, describes that kind of situation. Guinevere and Lancelot were in love but also loved King Arthur. So, they kept their feelings to themselves—until one fateful day when they broke their silence to each other. Later, Guinevere sings:

The silence at last was broken!
We flung wide our prison door.
Every joyous word of love was spoken.
And now there’s twice as much grief,
Twice the strain for us;
Twice the despair,
Twice the pain for us
As we had known before.

If you think you cannot keep your feelings to yourself any longer, you will be better off finding another place to work, to save both of you a lot of trouble. However, you say you have been able to be around her for two years, enjoying having her confidence and comradeship. So, perhaps you can continue a bit longer to see if things change for either of you.

2. How much do you need and want your job? If you think you could easily find work you enjoy at a similar wage, in a good environment, you may find it better to switch jobs than to continually censor yourself and your feelings. Then, you would be in a situation where you could talk to your current manager as a former employee and perhaps find out if something personal develops.

If you can’t easily find comparable work, you will be better off controlling your impulses and holding on to the job for a while longer—especially if you are doing well, establishing yourself and having the opportunity to move up in the company.

3. How likely it is that you two could have a personal relationship, even if the work situation was different? You say it doesn’t seem she feels toward you in the same way you feel toward her. You also imply that she doesn’t mix personal and professional relationships and seems focused on her work and her family obligations.

Consider the two of you outside of your work situation: Are you close to the same age or at least close enough that there isn’t any obvious disparity? Are your lifestyles away from work similar? (If she has a child and you don’t, there are probably big differences. But what about other aspects of your lifestyle as compared to each other?) Is your education and training about the same? Can you see yourself in her world and her in yours, on a regular basis? How do you think her peers would feel about it and how would she react to their opinions?

If it would be quite a reach to imagine the two of you together in most situations, you may need to just accept you probably will never be with her in the future in a personal way. So, all you have is what you have. Can you deal with that?

If you think you really could have a life together and that she is likely to recognize that as well, maybe it will be worth it to you to work elsewhere so you put it to the test.

4. Is there a chance you could be promoted, so your subordinate role to her will change? If so, why not work toward that goal, so you can interact to her as a peer or close to it, rather than in a boss and employee role? You might then have an opportunity to spend more personal time with her or ask her out or just let her know how much you like her.

5. You obviously admire and respect your manager. Since I’ve quoted Broadway lyrics already, let me remind you of the words from a song in The Man of La Mancha.

To dream the impossible dream,
To fight the unbeatable foe,
To bear with unbearable sorrow,
To run where the brave dare not go.

To right the unrightable wrong,
To love, pure and chaste from afar,
To try, when your arms are too weary
To reach the unreachable star.

It is very difficult to love from afar and not let your feelings show. But, when you know there is a potential for harming the other person or causing them embarrassment or distress, the truest way to demonstrate love is to not express it verbally, just feel it.

The best thing about that approach is that you can still let your love for your manager show in many ways for which she will be grateful, without her being aware of the depth of your affections. You can continue to do excellent work that presents you in the best way professionally and supports her work as well. You can encourage her and be a strong advocate at your own level. You can add fun and enjoyment to work, without being flirtatious or inappropriate. And, you can care for her while not blocking yourself from having relationships with others.

Keep in mind that a big consideration is how you want to live your life as time goes by. If you stay there and love silently but devotedly, you not only do not get the expressions of love in return that you might like, but you may be oblivious to opportunities for relationships with others. Time will pass and you may still be enthralled with someone who will never be yours.

Then one day, your opportunities will dwindle and you may realize what you have missed while you waited, in vain, for a friendship to become something more.

Before you decide whether to quit your job or stay, think instead of how you want to move forward in your life and what you want to do with all you have to offer. Combine that with thoughts about the questions I posed, above, and see if that helps you decide what to do next. It doesn’t seem that you have a timeline pressuring you, so give yourself the time you need.

Best wishes to you. If you want to do so, let us know how things develop.

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.