I Am In Love With My Boss But He Doesn’t Feel the Same Way. Should I Quit or Stay?

A Question for the Workplace Doctors: Should I quit my job
or should I stay and hope for a closer relationship with my boss?


I have been working in my business for more than 3 years now. I started as a part time worker and now my boss is willing to give me a certain percentage of the company shares, due to my hard work. We both have a good relationship at work, despite having a few arguments and disagreements about work. In fact, his mother and I get along well and she is my main support whenever we have issues at work, since she is also a part of the company.

I have come to realize that I have feelings for my boss and it is not just a ‘crush’.  Unfortunately, he is currently dating a foreign model. He has no idea if they are going to marry each other as they both practice different religions.

A few months ago I had issues with a colleague and it made me want to quit my job, even though the job means a lot to me. It was extremely hard for me to say I would quit, especially when my boss has future plans for me here. He is not a perfect employer when it comes to management, but I know I will never, ever find an employer like him and his mother. However,  I finally had the courage to send him my resignation letter. As I expected, he refused to read it, since he believed we had solved the problems.

He even refused to discuss and listen to my words on why I wanted to quit and what the things are that are really bothering me. His mother wanted me to re-consider my decision because she loves me like her own daughter.  Because of my boss’s mother, I changed my mind.  I didn’t have the heart to do this to them, especially when he told me that he might sell the company if I can’t solve the issues that I have with his friend (my colleague).

I could see from his behavior that he was very disappointed with my talk about quitting. He avoided me and pretended not to listen or to understand, whenever I raised the resignation issue. I know he will have a lot of trouble finding a replacement, because he can’t pay a salary that would be appropriate for the amount of work I’ve been doing. Perhaps that is the main reason why he wants to make me his partner, so that I will stay.

After all of this happened, I thought I could move on and focus on my job, even though it crushes me to see my boss with somebody else. However, I can’t just move on. Deep down, I hope I have the chance to have something with him, even though I know I have to be realistic. I am aware of all his flaws and issues as a boss and also as a man. He rarely tells me about his life but I have learned more from his mother. She keeps advising me to be more patient with her son and the relationships he has with women. In fact, she knows that I care about her son very much. She has told me that she is happy to have me there to help her son, especially when he has problems.

I know he will never want me to leave, which is the reason why I think it is the best for me to tell them my feelings and find a new job. I can’t imagine myself working at another place, but maybe it is the best for me as I can’t just simply sit and do nothing when he is in a relationship with another woman. He is the kind of guy who has lots of female friends and many of them are models and celebrities who are always flirting with him. But, that is not the reason why I fell for him, because he never flirts with me. Our relationship is completely professional and I can openly tell him what I like or dislike when it comes to work.

Last year, they hired a new female staff member and started giving her some of my work and I was happy about it. My boss told me they were doing it, “because you are important to me”. He said he didn’t want them to ‘touch’ me as he needed me for other things. He then, rephrased the sentence when he realized that it could have a double meaning. I know he just sees me as an employee and doesn’t want to give a false impression.

One of the things I appreciate about him is his willingness to listen to me and acknowledge my presence at work, especially when his friends don’t really like me. However,  I keep asking myself what I see in him, as he has too many flaws as a human being. He is not perfect. But I’m willing to deal with all that for the rest of my life, because I love him.

So, should I quit and move on or stay and try my luck with him? I know I have a slight chance to win his heart, but I refuse to make a fool of myself. I want to tell his mother about my feelings, so she can help me to convince her son to let me go, if leaving ends up being my only option.

We provide advice about workplace communication issues and about effectively dealing with various workplace challenges. However, as you may have seen, we receive quite a few letters about office love affairs. The reason we respond to those is that such situations inevitably have an effect on the entire workplace.  Even those who are not directly involved can’t help but be distracted by it. In your situation, the tension created by you having a stronger personal feeling for your boss than he apparently has for you, has had an effect on you, your boss, his mother and probably others.

A popular theme in modern romance novels is about the boss who has many beautiful girlfriends but one day realizes the woman he really loves is working right next to him–and they get married and live happily ever after. Even the titles can lead a hopeful young female employee to dream: “Courted By The CEO”, “When Love Is Blind”, “Elevator to Love”, “Beauty and the Boss”, “Loving Overtime”, “Forbidden Flirt, Lasting Love”, “Love Is The Bonus”. (I took those from a list of Boss-Employee romance novels.)

In real life, often an employee (usually a female) becomes emotionally involved with the boss (usually a male), because they share many of the emotional issues of work and become allies, friends and partners, almost like mates at work. If one or both are married, it can lead to broken marriages and ruined careers. You and your boss are both single, so there would be no moral barrier for you to be together. But, it doesn’t appear he is as obsessed with you as you are with him.

Here are some things to consider as you plan what you want to do:

1.) Could you get a job elsewhere that would pay you about the same amount of money, maybe for less work? Would your benefits be better elsewhere? If you could reasonably easily find a good job somewhere else, maybe leaving would not only give you a better work environment, you would also give your boss a chance to miss you and to realize what you mean to him. There is also the chance that “out of sight, out of mind”. But, at least you should consider your financial well-being when making your decision.

2.) Has this  business “partnership” your boss has mentioned, been scheduled? Is it more than “maybe”? If you are so indispensable that you can go from being a part time employee to having a financial share in the business in three years, congratulations. But, if I were you, I’d wait to see the money in my paycheck or the stocks in my portfolio, before I believed it. Consider pushing a bit to get a commitment about when you will begin getting a share in the profits of the business–and if the business is likely to be very profitable for years to come. If you are close enough to be considered for partnership, surely you can talk about the financial future.

3.) Are you the next level to your boss organizationally or are there others who have higher rank than you? Or, is the business just a three or four person office and there is a limited upward career path for you to develop? You mention other employees, so apparently you are one of a few. Where do you fit into the bigger work group? What kind of advice do you think your boss would get from others, if they thought he was considering a personal relationship with you?

4.)  Do you like the work and the other people there so much, that even if the boss gets married and the mother retires, you can stay and work happily for quite a while or even the rest of your career? Or, is your enjoyment of the work dependent upon the boss having you as a special person in his life and the mother loving you like a daughter? Those are certainly positive things, but things change.

5.) How long do you think you can go on as it is now, with you wishing and hoping your boss will have a romantic feeling towards you and your boss apparently only interacting with you at work and about work?  If he is intelligent and aware, he must surely suspect you have personal feelings toward him, but he apparently hasn’t indicated that he is interested in you romantically, sexually or for a date to social events. If he has hinted about those things, maybe something will change. If not, you may find that the window of opportunity for you to be more than an employee has closed.

You mentioned that you might tell your boss’s mother how you feel, with the idea that she will convince him not to try to keep you there if you want to leave. You don’t need your boss’s permission to leave, just leave. But if your boss is like most strong adults, he will resent you using his mother as a messenger. If you must tell someone how you feel, tell your boss. At least you will know where you stand with him after that.

If you think you can be an effective employee no matter what your boss does with his private life and you like the work and are being paid very well, you might as well stay. If you will only be miserable and end up quitting anyway, if he doesn’t finally become involved with you romantically, you should be  be looking around for a better job–and a life with someone who cares about you enough that he wants to be with you, not with others.

Best wishes to you with this. If you have the time and want to do so, let us know your decision and how it works out.

Tina Lewis 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.