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How should I handle the crush I have on my boss?

Tagged as: Troubled relationships<< Previous question   Next question >>
Question - (22 December 2010) 4 Answers - (Newest, 23 December 2010)
A female United States age 30-35, anonymous writes:

Short story: I have a crush on my boss. How should I handle it?

Long story: I have been working with a new boss for some time now, about 2 months. We work in retail together and I always have a lot of fun working with him. We joke around and make up inside jokes and laugh, and it makes work less stressful for me. Now, I'll admit, at first I wasn't attracted to him at all. He's not really the type I usually go for. But as I got to know him better, he grew more attractive to me. He's single, so there's a plus. But he is 9 years older than me (I'm 21, he's 29 and about to turn 30). He flirts with me a lot in an innocent way, and I flirt back. I have a feeling that he may feel the same way about me, but I don't know if I'm mistaking friendliness for flirtation. I don't want to say anything too specific, but I will say that he finds reasons to touch my arm or tickle me and he has told me a few times that he thinks I'm very pretty. So I know he is at least attracted to me.

My problem is, like all workplaces, fraternizing with supervisors is strictly forbidden. Even a casual relationship could result in both parties losing their jobs. I don't want to put him (or myself for that matter) in jeopardy, but I also don't want to throw away my feelings for him. What do I do?

View related questions: crush, crush on my boss, flirt, my boss, workplace

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A male reader, anonymous, writes (23 December 2010):

I'm a boss, and doing this with the help is not kosher.

In one of our businesses, we had a business partner who did this, what you describe, with one of the staff members. He was asked to leave, losing a very, very, very nice job and a partnership. The female employee was not asked to leave.

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A male reader, dirtball United States +, writes (22 December 2010):

dirtball agony auntYeah, I think you should go for it. You like each other. Just make sure it doesn't carry over into the workplace. You need to be good at keeping those aspects of your life separate.

How involved is the upper management at your retail location? If it's like most places I've worked at or known, they would likely never find out because they are never there.

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A female reader, SirenaBlusera Mexico +, writes (22 December 2010):

SirenaBlusera agony auntI can understand why workplaces have those rules (because the employee dating the boss could easily get preferential treatment). However I think it`s stupid for companies to tell people what they can and can`t do in their private lives.

You don`t get many chances in life to be happy. I can attest to this because I have been in unrequited love so many times. FRATERNIZING could result in both of you being sacked, but it`s clear he`s attracted to you. Furthermore, you`re between 18 and 21, and you`re both adults. He doesn`t have a girlfriend or wife, so you wouldn`t be doing anything immoral by getting involved with him.

He certainly wouldn`t go to jail if you got involved. In my situation, I would feel horrible about putting his job in jeopardy.

If you have a chance to talk to him privately about your feelings, you should go for it. Talking to him isn`t fraternizing, it`s free speech. You don`t get many chances to be happy. He doesn`t like someone else, he doesn`t have a girlfriend, he isn`t married, he doesn`t live in a foreign country, he isn`t gay (every man I`ve had feelings for has at least one of these characteristics). Meeting someone you like who reciprocates your feelings doesn`t happen every day, retail jobs are a dime a dozen. Would you be willing to work in a different place or at least another department, if you guys decided to date? I knopw that it`s not super easy to find jobs, but if you are sure about your feelings for him, you shouldn`t miss your chance... but be responsible.

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A female reader, dersita Ireland +, writes (22 December 2010):

dersita agony auntOooh girl crush crush! ;P You're in the twist of love :D

I totally understand what you mean. But it is true. You gotta make sure your feelings for him stay within you or both of you are BOUND to LOSE your jobs.

You like him + He likes you = Both like each other.

But think about it. If you do tell him you and you start seeing each other, sooner or later your love affair will BUST. You CANT let that happen. Dont lose your job on a person thats nearly turning THIRTY!

He's probably nice and attractive but I bet if you hide your feelings for a long time and dont make it obvious then trust me, he will LET YOU GO. He wont LIKE you LIKE you anymore. He'll just LIKE you as a friend.

THEN you can get a person your own AGE!!

TRY HARD AND SUCCEED!!!

Xxo

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