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I have a lesbian crush on my boss. Should I tell her?

Tagged as: Crushes, Gay relationships<< Previous question   Next question >>
Question - (23 November 2015) 4 Answers - (Newest, 24 November 2015)
A female United States age 26-29, anonymous writes:

I have a lesbian crush on my boss. I recently broke up with my boyfriend of three years after coming out as gay, so she does know I'm into women. I have a feeling she may be into women as well, she has never spoken of a boyfriend and in past conversations has admitted that she used to "mess around", but I've never actually asked her if she is. I have been working with her for over two years and we are definitely closer than just manager-employee. My only hang ups are the fact that she is my manager, and she is ten years older than me. Since I came out she is touchy-feely with me and I seem to notice us making a lot of eye contact. She also smiles at me a lot more than others and we are always together and talking at work. I've never been out with her outside of work. She is not the kind of person who is close to many people and actually seems unapproachable to most, so I know it's not just "her being her". But on the other hand she has said she doesn't like hanging out with employees outside of work because she feels like they may not respect her (granted, that was said before I came out to her, but this is the reason I've never actually suggested we grab dinner or anything). I'm terrified of ever telling her about how I feel, even though I really want to, purely because of the fact that she is my boss. However, these feelings are not going anywhere and I'm driving myself crazy over analyzing this. I'm looking for an unbiased opinion as to whether or not she seems interested. Any advice on how to handle this is greatly appreciated.

View related questions: at work, broke up, crush, crush on my boss, lesbian, my boss

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A female reader, Ivyblue Australia +, writes (24 November 2015):

Ivyblue agony auntMy advice would be don't go there sister! Reason 1: intimate relationships between bosses and employees don't always end well, usually for the employee and Reason 2: making a move without knowing for sure what her sexual preference could make for some rather uncomfortable tension. There are far more relationship opportunities than there are good jobs.

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A male reader, Garbo United States +, writes (23 November 2015):

Garbo agony auntYour job is not a place for romance. Many companies have rules on job romance and even if they don't, they can invent them in order to quell such behavior if they deem it detrimental to performance s d that can get you both removed. People have crushes on all sorts of people, but in general, if you don't see any future with a person, down a long line, then there is no point in engaging in a relationship. I would personally stay away from this one.

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A female reader, YouWish United States +, writes (23 November 2015):

YouWish agony auntI think work is where you keep things professional. Gay or straight, your job is your livelihood, and you do your job and that's that. I wouldn't have even suggested getting so personal with your boss about your sexuality with the long story about coming out after your breakup or asking her about "messing around". Work is work, and getting into experimentation or a relationship with your boss can certainly jeopardize your job AND HERS!

Keep things professional from now on.

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A male reader, Been there Now over it United States +, writes (23 November 2015):

You know you shouldn't be intimate with your boss and just to hear that is not why you've come here seeking advice.

If you have to move ahead with this: Find out first if she is bi or lesbian. You don't want to make a move under wrong assumptions. Second, make sure you have plans for other employment should this blow up. She seems like the kind of girlfriend who could get strange on you and be big trouble.

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