How do I approach my female boss about a possible relationship?

Question

We are roughly the same age, and in similar situations as far as family. I know she has two daughters, I have two as well about the same age. When I mentioned that I was extemely unhappy in my marriage and planned a divorce in a couple of years, she made a definite point of telling me she was unhappy in hers as well. We just started working together, by the way, but different shifts entirely, unless we have a meeting, I never see her. Well, I was attracted to her, and thought I felt the same from her, though she could have been being nice. Our main way of communicating would be through our work's email, and that is easily read, and saved, so I don't think she would be comfortable with anything personal sent that way. I've thought of sending her my private email, along with the suggestion that if she ever wanted to discuss "family" issues, she'd be more than welcome. Any ideas of that being a good idea, or suggestions would be helpful!

As I suspected, I didn't get an answer to my question. While I appreciated the moral pontificating, I would like an answer closer to my question. Also, there's no point in questioning my mental faculties, these points have been weighed. You don't know me, or my life, or the care I've taken in keeping my wife from the mental hospital's and killing herself with drug and alcohol abuse. Nor do you realize that I have single handedly raised two, well adjusted daughters even with their own suffering. Does anyone actually have an answer to my question?

Answer 1

Do not read anything into what she said you would have to be stupid to think that there may be something there for you. I would need to have met her off the work place and talked in natural way if its meant to happen it will just be patient. Also get your own life into order first if you are to break with your wife your boss will hear of it and just might take action .

Answer 2

Don’t get your meat where you make your bread. That’s what I would usually say to a question like this, but if your boss is reciprocating interest in you. I think you should take her out to lunch one day and take it from there. But I wouldn’t rush into anything because 1) you both appear to be in relationships that are not working and could quite possibly end in divorce. 2) You both have kids, and you don’t want both sets of kids getting familiar; what if the relationship doesn’t work out? I have one question though; does your wife know you’re planning a divorce in a few years? If she doesn’t that’s messed up lol. I would recommend you tie up these loose ends with your wife before you explore new territory.



~Dude calm down. Every body who responded did so with the initial infomation that you provided. No one knew all the extra details that you added because like you said we don't know you! It's clear you're looking for some justification for a mistake that you already made or will make in the future. Well you can get that in person...you don't need yahoo answers for that.

Answer 3

what you are suggesting is a very slippery slope....in most companies...dating is frowned on but it is a major no no for boss and subordinate to have a relationship.....she could actually lose her job because of it. Additionally, you don't say if you are both still married or if you did get your divorces? Be very careful and think twice...what happens if you have an argument or break up and it's nasty...and don't say that will never happen.....don't do it.....good luck

Answer 4

Use your head and get the divorce first. Why would you want to complicate both your lives (and your children's lives) if you can't do anything about it yet? Even if you start this relationship with her, you'll still have to get the divorce.
If she's someone you really want to be with, you should start the relationship right. End your current relationship before pursuing another one.