How Can I End a Relationship With My Boss But Still Work Well With Him?

Question: My Boss and I started dating this year for about 9 months. As normal or should I say as expected, some of the feelings are going away. I feel hurt because some of the things he normally does, he stopped. Calls, special attention, stealing kisses.. especially the morning calls and show of affection. It sometimes makes me brood at work as well. I forgot to add he is married. The last months have been so wonderful, too good to be true even though I know it was just for a matter of time. These days, I feel and know it’s coming to an end.

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What About Just A Hook-Up With My Boss?

A question to Ask the Workplace Doctors about sex with the boss.

Question: I really like my boss, but I just want a hook up. No dating, no relationship, no commitments, nothing like that.

Answer: We’re a site about workplace communication issues, rather than an advice column about romance and/or sexual activity. However, you may benefit from a reasonable and practical response to your question.

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How Should I Handle Having Romantic Feelings For My Supervisor?

Question: I’m 29 years old, in a long term relationship. My supervisor is a few years older than me, also in a relationship. We’ve worked together for quite a while now. Over time, after working directly with him on my shift, and slowly getting to know him, I’ve found myself caring about him more than I would normally care. Also, I found myself slowly attracted to him because we share many similar interests and get along well. I noticed my feelings for him after realizing I blush around him and get shy.

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Crush Leave Me Tortured Where I Work

Question to Ask the Workplace Doctors about being attracted to one’s boss:

Hey so I don’t typically do this but I could really use advice and I hope I won’t be judged for feeling the way I do..

SO.. a couple months ago I started a new job. I am a openly gay male btw. So I was hired and I loved the job ( I’m a restaurant server). I’ve been doing everything that has been asked of me and not to toot my own horn but I’m a GREAT server. So to speed things up My GM at my store is gay as well but more discreet about it. I had my eye on him when I first saw him (my second interview), but assumed he was straight and of course my potential boss so i didn’t think anything more. a couple days later I saw him on jack’d. Once i got the confirmation he was gay. I started crushing on him. Noo.. I didn’t bring it up at work that I saw him or even message him. As I worked with him more though the interest i had in him started to grow.

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I Like My Boss A Lot! What Should I Do?

Question: I really like my boss. He is super nice and funny and when he is around me, he makes me laugh like crazy! He makes me smile 24/7. I really care about him and his feelings.

He recently broke up with his girlfriend after they had a huge fight. I asked him if everything was okay and he seemed really down, so I tried to talk to him and he seemed a little bit better. I wanted him to be happy, so I asked him what he wanted most and he answered ”A K-Bar”. It’s a type of knife. So, one day I looked on Amazon and bought it for him. When I went to work and gave him the gift he was the happiest Man Alive! I had never seen so much joy and happiness on his face!!

But, I really don’t know what to do. I really like him. Sometimes he will play around and act like he will smack my butt. Does that indicate that maybe he feels something for me? Every time I go to work he always gives me a BIG smile when I walk in the room. I need some advice because I don’t know what to do.

Response: You don’t say if your boss owns the business or if both of you are employed by an organization that has managers above your boss. If you are both employed by a company, be aware of the restrictions on relationships between bosses and employees. There are so many problems caused by such relationships, that most companies forbid anything that could even seem to be personal rather than professional. Your boss could be fired over what has already happened (taking a gift from an employee). You could be fired too, for giving him the gift. He could also be fired for encouraging your affectionate feelings for him.

So, one of the first things you should do, to protect your job and his, is to take a realistic look at what would happen if he was seen touching you, swatting you, taking gifts from you or behaving in a way that seemed romantic and personal, rather than focused on getting work done. If he owns the company and it is only you and him there, maybe you can continue your current behavior. If not, think about what you are risking.

Also, think about the reasonableness of a man who makes probably twice or three times as much as you do, taking an expensive gift from you. You shouldn’t have bought it, but he could have refused to take it. If he wanted a KA-BAR (K-Bar) knife so much, he could have bought it himself. I’m sure it did make him happy to get it, but that isn’t the point. The point is that buying your boss a gift to help him get over his bad feelings after breaking up with a girlfriend, isn’t a reasonable way to build a good relationship—personal or business. And it isn’t a very mature way for a male boss to behave toward a younger female employee.

I want you to also think about this: You knew he had a big fight with his girlfriend. You knew he was upset and depressed. Why would you want to give someone in that condition a military-style survival knife? I get the impression you don’t know your boss in any way except at work. You don’t know his girlfriend either—or what led to the fight and the break-up (except what he might have told you.) You don’t know his medical condition, his psychological condition or anything else about his personal life. You should not have gotten involved with any aspect of his feelings. Remind yourself that you are an employee, you are not a counselor. I also get the impression you are still of a youthful age, so you don’t have years and years of experience to guide you or to help you guide him. You can hurt someone rather than help them, by getting involved in a situation you don’t know about.

However, I realize that if you feel a lot of affection for your boss, you probably wish you could know for sure how he feels about you and if there is any future for the two of you. One way to know for sure is to quit your job and see if he still wants to spend time with you, when he can do it without any risk of getting in trouble. Instead of a few minutes of having fun at work, you might be able to spend a lot more time together. If you quit and find another job, then call him and ask if he’d like to have lunch or coffee, you’ll find out right away how interested he is in a relationship. I expect you don’t want to risk your job to find out, but that is one way to do it.

Or, if your job is not the one you intend to have for the rest of your working life, you could mention to your boss that you’ll have to find another job one day. Let him think about the time when you won’t be there. If he wants to have a personal relationship with you, he may say something about it then. If he says he’ll miss you at work, you could remind him that the two of you could still get together for coffee or just to talk. You might be able to tell by his reactions to that comment, whether or not it’s something he’s interested in.

You could mention a movie you’ve seen or a concert you’ve attended and you could say that you thought he would have liked it too. Then, you could say, “If you weren’t my boss, we could go to something like that.” See what he says. Or, after the two of you have laughed about something, you could say, “I think we could have a lot of fun away from work. If you weren’t my boss, is that something you’d like to do?” (If he says no, it will be very embarrassing. But, if he says yes, at least you will know where he stands.)

The risk of asking him or hinting strongly to him, is that he might feel pressured about it and look for ways to remove you from your job. That wouldn’t be good!

Another risk is that he will think you are available for a sexual relationship, without having a real dating relationship. If he has been sexually active with his former girlfriend, he will be looking for sexual activity elsewhere and may think that is what you’re interested in too. That could be disastrous for you in many ways, so be very, very careful about suggestions he makes that might involve more than you intended.

So, that brings us back to your question: What should you do? The answer to that will depend upon your ultimate goal for the relationship. If you just want to be able to laugh and enjoy your boss’s company, you can keep doing what you’re doing right now. Be a good employee and help both of you be successful in the company. If your goal is to date him and maybe to eventually be married to him, you will probably need to leave your job so the two of you can be free to know each other away from work.

Another question could be: What should you NOT do? My comments already have pointed out that you should not get involved with your boss’s personal life. You certainly should not buy any more gifts for him. You should not do anything that could cause gossip and speculation among other employees. You should not settle for only a sexual relationship. You also should not assume your boss is interested in you romantically, just because he likes you personally. Maybe he feels romantic, maybe he doesn’t. The old adage that “time will tell” is true here. For right now, focus on work and on being a valuable employee and coworker and give it a bit more time.

If you have a trusted friend or relative who has had successful relationships in his or her life, perhaps you could talk to them about the situation. They would know you and be better able to provide personalized advice.

Best wishes to you! If you have the time and want to do so, let us know what you decide to do and what happens.

Tina Rowe
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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: read more

Why Do Women Flirt???

Question: Why do women flirt???

Response: Your question was brief.  The three question marks you placed after your question, appear to indicate frustration over the subject! Our focus is on workplace communication issues. However, on the chance that you are perplexed about the behavior of women (or one specific woman) where you work, I’ll share a few thoughts. If you have a specific work situation in mind and want to provide further details, let us know.

Flirting is behaving toward another person in a way that could be interpreted as indicating attraction. Like a bird ruffling its feathers in the direction of a potential mate. However, with people—men or women—flirting comments or behavior may not indicate serious interest at all. Often it is intended only to get a similarly flirtatious response, usually for short-term amusement and sometimes to see if anything more serious develops. read more

How Can I Keep From Working Near the “Other Woman”?

I recently found out my husband was having an affair with a “friend” and coworker of mine. All three of us work for the same company in different departments and different buildings. However, this week, the other woman shows up in my office and is now working in my department. Is there anything I can do to get moved to a new department with out jeopardizing anyone’s employment? I don’t want to bring this painful personal issue to my work place but I cannot go to the office every day and see her.

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Will My Husband be Fired if I Tell About His Office Affair?

A question to Ask the Workplace Doctors about whether or not an employer would fire two people who are having an affair. 

My husband was recently promoted to a high level manager’s position in an industrial plant. He was placed on what is called a hiring panel with the HR manager to recruit and hire new employees. The HR manager is also married.

Shortly after working together and her sending many inappropriate text messages to him all hours of the day/night, he began the affair with her. She recently put him in for a company recognition award which he got.

My question is, if I let corporate management and the plant manager and general manager of the plant know, will they be fired? I have evidence to prove the affair.

I feel this is unethical and a conflict of interest on the HR managers role in this, not taking sides with my husband, for I am pursuing a divorce.

Our Response: I’m very sorry about this situation. I can well understand the sorrow and anger that you have felt and will continue to feel for some time. (It may be that there was some other conflict or problem before the affair, so this was just the last straw.)

I realize you didn’t ask us for counseling about your marriage, but I hope before you finalize your divorce, you will consider whether you and your husband could work together to rebuild your relationship and move forward. That would be especially true if you have children, no matter what their ages. Once the parents are divorced, life is never the same for the rest of the family.

However, whether or not you stay married, there is still the question of should you or should you not tell higher levels of management about the affair between your husband and the HR manager. There are things to consider about both options.

If you decide to notify higher level management, they may or may not think of the situation as a firing offense or even a reason for a sanction of any kind. Your husband and the HR manager worked together, so one was not subordinate to the other. A relationship with a subordinate employee would be viewed more negatively in most businesses and might be considered a firing issue, to avoid later accusations of harassment or intimidation by the senior person over the subordinate.

More than likely, many people already suspect or know that your husband and the HR manager are in a relationship. Some of the people higher up may have such relationships themselves and will not be inclined to risk accusations of hypocrisy if they make a big issue about this situation. (Although, in most businesses, the number one rule is to be discreet—which apparently the HR manager and your husband were not.)

They certainly couldn’t fire one of the two without firing both, so it would be a big decision. I think it is more likely that there would be some reassignments, but even that would be difficult to achieve within the framework of most large companies. The HR manager most likely can’t work anywhere except HR and your husband’s area of work would stay the same. And, from the business viewpoint, the company would lose two managers over something that is not illegal or unethical (since no harassment or intimidation issues are involved.)

On the other hand, higher level managers may decide the two were so indiscreet as to be a risk for other concerns about the business. There may be a viewpoint that they have failed in their leadership for their teams, if everyone is talking about the affair. Further, if they’re meeting in secret at work or engaging in emails, phone calls and texting, while they should be working, their responsibilities may be being neglected.

If there have already been concerns about the work of HR under the manager’s leadership–or about your husband’s effectiveness in his managerial role—higher management could put the blame on the affair and use that as a reason to remove them from their roles or remove them from the business.

Those views are all based on the “ifs” I stated. If both are doing great work and things are going well in their areas of leadership, the views of higher level managers would be much different.  Also, there tends to be a feeling of distaste on the part of managers and executives, about being drawn into such situations, even though they may feel sympathetic to the person notifying them.

As another option, you may want to discuss another approach with your attorney or with some other attorney. According to what state you live in, you may have legal options related to alienation of affections. (It’s an old law, but still used in civil suits on occasion.)

You should also consider if the HR manager could sue you, if she loses her job over a relationship which she could allege was started or encouraged by your husband. Or, she could say she was getting out of the relationship, but your actions ended up causing her husband to divorce her and thus harming her emotionally and financially. If she has children, she could include that in the reasons your actions created harm.

If something you intend to do could end up damaging someone financially or emotionally, it’s always wise to get a legal opinion about what the person on the receiving end could do back to you.

The final thing to consider is the more personal aspects of the decision to tell or not tell. If you hoped to have an amicable divorce, with fair division of property and child support (if any), you will reduce the chances of that happening. Or, you could wait until after all of that has been settled before notifying the workplace. You would probably lose any relationship with your ex-husband (and maybe even with his family), but it might be worth it to you, from the viewpoint of at least temporary emotional satisfaction.

The bottom line is that alerting your husband’s managers to the affair he and the HR manager are having may or may not result in their being fired or sanctioned. I can see reasons why you would feel justified in doing it, but I think you should consider the potential reactions and possible harm to your best interests.

If you have the time and wish to do so, let us know what action you take and what were the results. I wish you the very best through all of this and hope you will take care of yourself mentally, emotionally and physically, as you move through this and find a better situation for yourself in the future.

Tina Rowe
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