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Should I cross this risky line?

Tagged as: Crushes<< Previous question   Next question >>
Question - (6 August 2012) 2 Answers - (Newest, 7 August 2012)
A male United States age 36-40, anonymous writes:

So three years ago, I met this co-worker that absolutely blew my mind. She was special in every shape and form. I spent countless days trying to summon the courage to ask her out. When I finally did find the will, I heard she had relocated to another store outside of the state. That was the last time I've heard of her.

Now here I am, still working at the same dead end company. I've met many girls that I have taken out on dates within the last few years. I don't have the same problem in approaching girls as I did back then. I'm not going to say that I didn't meet any special girls within these last three years. Infact, I fell head over heels for one, two years ago. Long story short, we were together up until the beginning of this year.

Ok, here's where the meat of the story begins. Our store just got word we were recieving a new manager. We were all in the meeting when she introduced herself. Can you imagine my suprise/disbelief when that same girl who escaped three years ago was now back in my store. . .AS MY BOSS?

I couldn't believe how much she had accomplished in these short three years. I was impressed. But not only that, I was still deeply infatuated with her. I honestly had forgotten all about her when she wasn't here. Now having her standing right in front of me is bringing back so much emotions that I thought were gone.

Like I said earlier, I have no problems approaching girls now, but this is a totally different situation. The title she carries is something to worry about. She is now my boss and somehow I feel approaching her in a flirtateous manner can lead to disastrous results. I really find she's the perfect girl in every sense. We've talked on friendly terms since she's been back. She doesn't act bossy or anything. Infact, she acts like a regular associate. She works with us, laughs with us and even hangs out with us when we go on breaks.

It's like she doesn't even realize that she's our manager. I think this is how I got closer to her. How I got to know her better and how it was confirmed to me that I am crushing on her more than I ever crushed on a girl in my life. I've been fighting with myself lately to come up with EVERY bad reason NOT to flirt with her. I know that the consequences could be horrible. But it's like my heart doesn't care. It wants her and neglects every single obstacle that's standing in our way. Whether I get rejected or not, it wants an answer at the very least.

Everday I see her, it's like someone is hooking up booster cables to my heart and giving it a jump start. I don't know how much more of this I can take. Someone please help me. What can I do. Give me reasons I SHOULDN'T ask her out. Give me reasons I should?

View related questions: co-worker, crush, flirt, my boss

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A female reader, So_Very_Confused United States +, writes (7 August 2012):

So_Very_Confused agony auntDating someone at work who is a peer is tricky

Dating a boss is often not allowed.

Even here in the federal government spouses cannot work on the same team or in the same office...they are split up...

I can give you a zillion reasons NOT to ask her out

I cannot give you one good one to ask her... she is YOUR BOSS now and if she has made such a meteoric rise she is obviously a. doing something right and b. on the watch list and probably not going to risk her job for a date...

I'd let it go.

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A male reader, Sageoldguy1465 United States +, writes (6 August 2012):

Sageoldguy1465 agony auntYou shouldn't ask her out UNLESS you are OK with ONE OF YOU having to leave his/her job. Most companies simply will not allow dating between bosses and subordinates...

You SHOULD ask her out if you are OK with one of you having to leave his/her job...

Good luck...

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