A Remote Work Relationship Has Become Awkward.

Question: Unintentionally, I developed feelings for a supervisor, not my direct supervisor but a supervisor that assists me if I need help and even can hold me accountable if required. I work from home and just one day struck up a conversation which continued for months. I had no idea that feelings would develop and was mortified when I realized it.

I remained professional as did he, although he was a bit more forthcoming with mentioning that he missed me. I fully understood because we had great conversations. Now, he’s not communicating with me and when I ask for assistance he never responds; I solely get help from other supervisors.

I wanted to just normalize it by still saying hi, but he does not respond. Now, I feel just by me reaching out to say hi that I’m running the risk of be labeled a harasser; it’s quite embarrassing. So now, I’m in an environment where this supervisor is off-limits because I developed feelings which I never admitted.

He told me that I had space in my heart for him but, I would never admit it. I added my telephone number to an email and when he didn’t use my number that told me what I needed to know but, I still wanted to make small talk with him and let the feelings dissipate. They way that he has gone about it hurts. I’m going to be seeking another job.


Hello and thank you for sharing your concerns with us. I followed up with an email to ask you a few additional questions, but you may not have wished to answer those. Thus, I’ll respond to your question as you originally sent it.

What I’m confused about is that you apparently never encouraged the attempts of one of your supervisors to have a closer relationship. You essentially rejected his comments that you might have “a space in your heart for him.” However you worry that you might be viewed as a harasser if you try to communicate with him further. It seems to me the reverse is true and that may be why he’s not responding to your emails.

According to whether you or he is married or in a relationship or how your company might react if they found out a supervisor and an employee had a personal relationship rather than only a business one, he may feel guilty, afraid of getting in trouble, or afraid he said more than he intended and wishes he hadn’t.

I don’t think he is handling the situation the right way, but I don’t know how far the conversations went. If he really spilled his feelings for you, he may think the only way to deal with it is to cut off all conversations. You had some of the same feelings of mortification and embarrassment, so you can perhaps understand how he feels. (Keep in mind that you two wouldn’t be the first to become emotionally attracted through emails, phone calls and zoom meetings.)

He may also feel so strongly about you and his attraction to you in an emotional way, that he doesn’t think he can ever go back to a work relationship. If you keep an open and friendly attitude, maybe he can see that it is possible for him to have feelings for you but not do anything about it. If you work in different cities or if you will  never be working together in an office there won’t be a chance for anything else anyway.

He may feel if he calls you, you will think he is being pushy even though you have not encouraged him. If you want to normalize things, why don’t you be the one to make the call and get the awkwardness out in the open and over with?

For example, “Hi Greg, it’s Kim. Can I have a few minutes of your time?” Whether or not he encourages you, if he doesn’t hang up, just say a few sentences and let him know you’d like to have a comfortable friendship with him, as you did at the beginning.

Like, “I’m calling to let you know that I’ve appreciated your support and help about work and I don’t want us to lose the great conversations we’ve had over the last year. So, if I send you work emails, can we start communicating again?”

You don’t have to give a big speech, just something brief like that example. If you give a breathless speech you will be uncomfortable and make him uncomfortable while he’s waiting for you to finish. Leave emotions out of it and focus on wanting to continue having a great work friendship.

He may not feel he can have a supervisory/employee relationship with you because of how far he let things go. Maybe you can improve the situation by communicating with him about something where he will have to give you guidance, direction or information. It sounds as though your recent communications haven’t been so important that he absolutely has to respond, so change that.

He may feel offended that you seemed to reject his emotional advances. It may be that you are not the only one he has flirted with or acted romantic about and he resents that you, an employee, weren’t impressed enough to respond to him. That may not be the way he is, but it has happened before so I thought I should mention it.

If that is the case, the suggestions to call him and see if you can return to a former level of communication might help him feel better about it.

Since I don’t know how far the conversations went or what options you have for getting back to better communications, my suggestions may need to be adapted for your situation. But the bottom line is that you will probably need to be the one to improve things.

If you can easily find another job and think that is the only way to deal with this, your decision about quitting may be correct. But if you like your job and are getting paid sufficiently—and if you can continue to work from home, which is a great benefit—it doesn’t seem to me you have a strong reason to quit. There is nothing about this situation which can’t be overcome if you accept that it isn’t unusual and that others have been able to keep friendships while calming down the romantic or emotional part.

If you have the time and wish to do so, let us know how you handle it and the outcome. Some of our readers may find your situation to be like theirs and they can learn from you.  Best wishes to you.

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.