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I have a crush on my boss, should I tell him?

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Question - (23 August 2009) 8 Answers - (Newest, 26 August 2009)
A female United States age 26-29, anonymous writes:

I have had a huge crush on my boss for the past seven months but have not done anything about it. I joke with him as I do with the other employees at work but I don't flirt with him because I know that a relationship with the boss is not appropriate. He may be fired soon for something he did wrong. He actually called me into his office to express his concern about this possibility. Now I don't know how to approach him on how I feel about him. I think if I don't say anything I will regret it. What should I do?

View related questions: at work, crush, crush on my boss, flirt, my boss

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A male reader, Code Warrior United States + , writes (26 August 2009):

Code Warrior agony auntThank you for your kind words. My wife would argue that she is not so lucky sometimes and I would have to agree! I am always a work in progress!

It sounds like you have built a sturdy foundation for your life and have no fantasies about him. I like that you realize that you do not really know him on an intimate level and are looking to proceed cautiously. That is wise.

If you can't bear to think about him not being in your life, that is OK. You don't have to. I even think it is healthy to visualize what you think life would be like with him - as long as you don't fantasize too much about it and start obsessing.

It is easy to start obsessing. Trust me. Had to kick myself a few times.... But I digress...

As fas as trying to go out with him, are you ready to handle rejection from him? I sense that you are more than capable of dealing with rejection from some other guy, but your statement implies that you are still a little fragile with regard to a rejection from him.

I would say that it is OK to ask him to go out to lunch or something harmless like that to see if you have fun doing that. Don't put a whole lot of emphasis on how well it went or anything like that, you are doing it more to get him used to the idea of being out in that kind of setting with you in a no pressure situation and don't worry if the conversation is about work.

Maybe you have already done that - if so continue. Hell, offer to buy. Nobody at work will refuse a free lunch unless they don't have time to go!

I would not advise taking it any further than that until you are ready to accept a rejection from him and can bear the thought of not having him in your life. Not that you will get a rejection or should expect one, but you should still be prepared to deal with one and be able to move on from it without resenting him for it.

If he does reject you - don't press him for a reason. Handle it with grace and know that it is not an indictment of you. People like what they like and they need to be allowed the freedom to say no without having to explain themselves. On the other hand, you need to believe that someone else will come along. They always do.

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A female reader, anonymous, writes (25 August 2009):

This took a while for me to think about. I am actually surprised at how many of the confidence steps I have already conquered. I have made a lot of progress in this area over the past couple of years even if I couldn’t define that it was confidence I was gaining. I have already learned to forgive myself when I make mistakes and to forgive others for their faults as well. I am not naïve. I don’t believe that I can change people nor would I want to. I have accepted that the world is made up of all kinds of people. In the case of my boss, I know he’s not perfect. I have seen some of his negative traits and he has done some things at work that have required me forgiving him, and I have. I have not been a perfect angel either. I have certain habits that I wish to change about myself and have made huge strides towards.

I lack in decision making skills and my direction in life is still fuzzy. I graduated from college with an accounting degree; I went into it for a while and determined I hated it! Now I am in a position that I like but the disadvantage is it does not pay well. One of my biggest struggles right now is finding that career that I love and pays well enough to live comfortably. I am sure this must be an issue for many.

Though I like to believe that I have an attractive appearance, I know that to some I will and to some I won’t and I am fine with that. There are traits in myself that I hope others see and find to be good qualities. I have had issues with depression for a greater portion of my adult life. Sometimes I have trouble seeing the good qualities in myself because of this. I sat down and thought about it a while back when reading on of Dr. Phil’s books and have determined which qualities I want others to see in me. I consider myself to be kind, compassionate, intelligent, humorous, at times, reliable, and trustworthy. I hope that these traits are reflected in my personality.

In thinking about what I want in a mate, I actually bought Dr. Phil’s book Love Smart. This has helped me define what I am looking for in a relationship. In the case of my boss, I don’t know everything about him. He has demonstrated kindness, patience in some very stressful situations, and he has shown me that he has a sense of humor. These are all qualities that I look for. He does not meet every quality I look for but to find this person would be impossible.

Do I love him? I think it would be going a little far to say this. Part of me wants to say yes but there is a voice in the back of my mind that says I have to get to know him on a more intimate level to know this. I think love has varying degrees, and I might be at the early stages of it. I do care about him and his well being. I don’t know whether or not it would be selfish for me to express these feelings for him when he leaves the company. Is it realistic to think that we could be together? Right now, I can’t bare the thought of it not being a possibility.

On another note…In reading your profile and some of the comments you wrote to others, it seems that your wife is a very lucky woman. To have a husband be that devoted in this day and age is a rare quality to find. I never really thought about what love truly means. This is something I will be thinking about for a long time to come. Congratulations on keeping off the weight!!! I know so many people who yoyo because they can’t seem to adopt a lifestyle change.

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A male reader, Code Warrior United States + , writes (24 August 2009):

Code Warrior agony auntIt is good to hear that you deal with your slip-ups and get back on track. It is also good that you are asking yourself the right questions.

I think you need to understand who you are and who you want to become. There was a post today from a teen who wants to know how to get confidence. I posted back a book outlining my 12 step program! Read it and let me know if any of it applies to you. There is also another post from a girl with an alternative look who wonders if she intimidates other men (Is my appearance holding me back?). I posted there too - another book.

There is also a post from a guy who is going though a tough time with his wife(She wants to seperate and I'm shocked and heartbroken). I posted there as well.

Those posts all deal with the fundamental issues: What is attractive, what is confindence, what does it mean to love someone?

The alternative look girl's post is a great read because it illustrates how deep you should go to understand yourself. Her description of her personality is eloquent and beautiful. I think it can help you figure some things out about yourself.

The post from the man who is concered about seperating from his wife is an illustration of how selfish feelings can be misconstrued as love. I talk a lot about what I have gone through in that post and maybe you will find something there worthwhile.

I honestly think that you should not enter into relationships without knowing what it is you are looking for in another person. This gives you the basis to determine if the person to whom you are attracted is right for you. It also helps you undestand exactly why you are with him, or in the sad event that it does not work out, helps you understand why you are leaving him. This knowledge helps you combat urges to return to old bad habits. It is the difference between making a choice and the choice making you.

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A female reader, anonymous, writes (24 August 2009):

I know he likes me as a person but I really don't know if he "likes" me in that way. He likes to joke around with me but as my boss he has never crossed that boundry which is a good thing. Honestly, I would probably lose respect for him if he did. I don't want you to think that every thing we say to each other is happy either. We've both have our days where we argue over one thing or another about the way the company is run. I get so mad at him sometimes. Despite this, I am still attracted to him.

In terms of self confidence, I have social aniexty disorder but at work itself, it doesn't really affect me. I am confident in the work that I do and the guests all seem to like my service. I get along great with the other employees as well. In the environment that he sees me in I am confident in myself. As for the attractiveness, I'm getting there. Most people don't find an overweight woman to be attractive. I still have some weight to lose but I can honestly say I am starting to look more attractive. Men have started hitting on me more. Sometimes it takes a third party to point it out to me though. So I guess you can say I am a little clueless to when men are hitting on me which is why I am not sure if he likes me like that. I know men are usually more direct but in a work environment you have to be careful with how direct you are!

As for the weight loss, I have asked myself that same question. I don't know if I will be able to maintain my weight loss if the relationship does not happen. I would like to say yes because it sounds good but this is a question I have asked myself as well. I know its important to continue down the path I am going and I have truely tried to make this a lifestyle change. Every now and then something happens in my life and I find myself reverting back to old habbits, which scares me. For now though, I concentrate on the fact that when I do find myself slipping I am able to find my way back to the healthier lifestyle that I began developing seven months ago.

Do you think it would be okay to start an out of work friendship with my boss or is this crossing the line as well? If so how to I go about initiating this without sounding to direct. I know a sexual relationship is out of the question, but I know he has been going through a lot lately and it kind of hurts that I can't be there for him. He called me in to his office and expressed his concern for the possibility of being fired. I know he did not call any other employees in to express this concern. (I casually asked some of the employees without revealing any real detail) Was he reaching out to me a little or am I reading to much in to it?

As for the less about him and more about me thing...This has definately been a life altering experience for me. I seriously have not had feelings for anyone in nearly 10 years. Late teens to early twenties was the last time I truely had feelings for someone. I have had a lot happen in my life that has made life unbearable at times. Sex and relationships were not my top priority mostly because acting happy around people really sucked. People want to be around happy people and I was not happy. Now I don't know what to do with these feelings I have for him. I spent several months trying to deny that I had feelings for him. I spent more time asking myself why him??? When I first met him, I hated him. I got along very well with the former owners/boss so when the change happened it took me by surprise.( I did not take to the change very well. The best answer I came up with, was he makes me laugh which not many people do, and I can relate to some of his goals for life. Sometimes he says things that I have not fully understood about myself. When he says it, it clicks in to place. This is the first time I fell for my boss though. I was never the type to have crushes on the teacher, boss etc.

I realize I just wrote you a book but I appreciate the advice if you have anymore. On a final note, I have had other men hit on me but I have a one track mind (dangerous, I know) but I am fixed on him for now despite how complicated this has made my life. Thank you in advance.

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A male reader, Code Warrior United States + , writes (24 August 2009):

Code Warrior agony auntI am puzzled why you don't have a clue whether or not he is attracted to you. Do you think that you are attrative? Are you confident? I believe that people are attractive to others when they have confidence in themselves.

I congratulate you on your wieght loss. I know how hard that can be - I lost 120 lbs a few years ago and have kept it off because I changed my lifestyle. My question to you is will the weight come back if this relationship never happens for you?

Using a potential relationship with him as motivation for losing the weight is as good as any other motivation. However, at some point you need to be doing this for yourself if you want to sustain your new look over the long term.

Perhaps this is less about him and more about you. Maybe you are just ready for a more serious relationship in your life?

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A female reader, anonymous, writes (24 August 2009):

I of course do not hope that he is dismissed from the company and the reason he may be let go has more to do with the downturn in the economy then his performance directly. This is the first man I have felt this way about in over ten years. I actually decided to lose weight in hopes of attracting him. (so far over fifty pounds) He is about ten years older than me, but my motivation comes from the fact that he will eventually not be my boss. I knew this from the beginning. The company I work for changes ownership and bosses every two years without fail. My job isn't that great. I like it alot but the fact is I would be willing to change jobs if I thought I had a future with him. I would not express my feelings while he is my boss, but I don't know how to approach him if something does happen to him. I fear that I will not get to him in time if he is fired. I do like the idea of asking for his personal number just in case I find a new job for him. The fact remains that I have no real clue if he likes me. He jokes with me and makes me laugh but that is a part of his personality. I refuse to give him any real signs that I like him because I don't believe in the work relationship. I know it spells disaster. I just need to know how to set it up for the period in time when he is no longer my boss. I could settle on friendship first. This isn't just sexual, I have found that I have real feelings for him.

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A male reader, Code Warrior United States + , writes (24 August 2009):

Code Warrior agony auntThis has disaster written all over it. You need a policy. NO DATING THE BOSS!

Reading between the lines, and please forgive me if I'm wrong about this, is part of you thinking that if he gets fired the conflict is resolved and you can pursue your romatic interest in him? I mean, I don't think that you want to see him fired for real, but maybe you wonder about the possibilities for you and him if that happens?

If so, realize that you would then be dating an out-of-work potential loser who may become a leach. I guess it depends on why they are considering firing him. You know why, and you also know if it is reason to doubt his character and reliability.

The likelyhood is that the relationship with the boss will not last and then you will be stuck working for a boss that is hostile to you. Even if the relationship is good, your co-workers are likely to assume the worst about you and you will likely be alienated from them. Then you will be stuck between him and your co-workers and your only options would be transfer somewhere else or quit.

Stifle your feelings for him until he is fired. If he gets fired, get his personal phone number under the guise of calling him if you find out about any job opportunities. Keep in touch by calling him from your work phone (never use your personal phone) and maybe even see him occasionally for lunch just to keep tabs. You need to see if he is a man of character and bounces back, or if he is a loser. If you see a man of character, then you can pursue him romantically with little repurcussions should it fizzle. If you see a loser, then you can just bail and never see him again.

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A female reader, starfairy United Kingdom + , writes (23 August 2009):

starfairy agony auntDo you think he feels the same way?

Tell him, what's the point in having regrets x

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