What Should I Do About My Feelings For My Boss?

A Question to Ask the Workplace Doctors about having a crush on a boss:
How can I know if he feels the same way about me? 


I’ve not worked in a place where my male boss has been so nice to me. He’s a sales person and talks the right way all the time. I know, as I was a gamer before. But then I felt his sincerity when he compliments me. He often compliments me and notices a lot about me. From my eyelashes that he said was nice, he even mentioned that my black eye liner looks better on me than the silver. He says my curled hair looks good. And I caught him gazing at me. When I smile while we talk or when I look him in the eye, he would look away. When we are alone for work, we always have good times. I feel so comfortable around him and in fact I enjoy very much being around him.

Lately, he touched me professionally, in a non-sexual way like tapping my shoulder to usher me out of the room and he does lean-in comfortably in a non- sexual way when we talk. He’s a very professional man and I know he’s a wise and kind person. So I don’t know if he’s just being nice to me or is he having some feelings too? He often says I’m very pretty and charismatic. I developed a crush for him and I’ve really been suffering because of it.

He’s married. Lately, he also spoke of his wife briefly. But at the same time, my instincts tell me he feels something too. I’ve been working hard and he’s impressed as compared to the rest of the team, I think more like him. We click and we are at the same level of thinking. He gives me some benefits of authority although I’m new in the industry. He allows me more benefit than others. He sometimes compares me with my colleagues and has said I’m so much better than them etc. He didn’t really like the idea of another male colleague praising me too much and he seems protective of me. Is it just a common thing a male superior would do for a female subordinate?

He also said I’m the best he’s ever hired and the best he can ever hope for. I feel empowered and protected by him actually. But how will I know if he’s into or not that into me? And what should I do? I can’t stop thinking about him. Actually, he’s very much of the dream man I’d want to be with. But I’m not that type of sleazy girl who does funny things. I respect myself enough. But I don’t know what to do… it’s tearing me apart.

He also mentioned to me about a story about a beauty and a CEO. I can’t find the answer to it. I’m probably just over analyzing everything he says.

Out of My Mind


Dear Out of My Mind

Hello and thank you for sharing your concern with us. To summarize your question, you wonder how to figure out if your boss has personal feelings about you—and what you should do about the feelings you have for him.

Your boss’s comments and actions certainly sound much more personal than they would be if you were a man–or if you were a woman he found unattractive. I think he is probably attracted to you in some ways, maybe many ways, and probably he is also aware he could ruin his life and career if he does anything about it. For one thing, there is almost certainly an organizational rule prohibiting relationships between bosses and subordinates. For another, he’s married. He risks losing both his job and his marriage if he does more than daydream about you.

I don’t think it hurts to feel a special connection to your boss, even to have a crush on him. The challenge, as you have discovered, is keeping your feelings to yourself. There is a tremendous temptation to want to know if he feels the same way–but knowing nearly always has a negative result. If he feels the same way, it makes it doubly difficult for the two of you to stay out of trouble and for him to do the honorable thing as a married person. If he doesn’t feel the same way, it will be embarrassing for both of you and he will regret treating you in a way you misunderstood.

Your boss should have known—and probably did know—how you would interpret his words and actions. He is obviously not shy or lacking in confidence, so if he wants to take the relationship to another level, he will let you know. Unfortunately, the only other level is a secret sexual one, unless he leaves his wife for you.

There is a song from the musical, “Camelot”, entitled, “I Loved You Once, In Silence”, sung by Guinevere to Lancelot. Look up the lyrics and you’ll get an idea of how much worse it can be to know than to not know. At the same time, look up the lyrics for “To Dream the Impossible Dream”. One phrase especially applies: “To love, pure and chaste from afar.” You may not want to be the heroine of this story, concealing your feelings to avoid causing heartache or creating harm, but that is what you will need to be if you really do admire your boss and want the best for him. On the other hand, if you think his motives may not be so admirable, you will be better off if you don’t put yourself in a vulnerable situation by letting him know his strategy worked.

My advice is to use this time of closeness with your boss to energize your work and help you gain more knowledge and skills. Make him continue to feel proud of his good judgment in hiring you. Make it a good feeling time, rather than one of unhappy longing or wishing. At the same time, realize that closeness between a boss and employee is noticed by others and may cause you problems, whether or not it goes further. Don’t let yourself be in situations where people could criticize either of you for what you know to be innocent actions. Keep this just a special friendship and relationship and you’ll have some wonderful memories of this time in your life and career.

Best wishes to you. If you have the time and wish to do so, let us know if something changes and what happens.

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.