Love and Confusion

Hi all,

I am new here and have been reading the forum for about a week. Here is my story:

I'm 47 (let's call me D) and the woman about whom I am writing is 32 (let's call her M). We work together in an office of about 45 people. I am the head of the office, and she is a fairly new employee. I do not supervisor her directly; there are two levels of supervisors between us.

Okay, I know what you're thinking: DON"T DO THIS-- work/love doesn't work in these circumstances. I know that. But please indulge me a bit and listen a bit more before you reach any conclusion. Okay? Thanks.

One more bit of background. We are both single and never married. I am unattached, and I'm not entirely sure about her. About 4 years ago I ended a long-term relationship, and since then have primarily laid low as far as dating/relationships are concerned and focused on my career, and sucessfully so, having worked my way up to the head of our office. Lately I have found myself ready to come out of my shell a bit and have felt ready to explore a relationship. I have had what I consider to be a number of healthy relationships. I am also well-educated and personable, making friends relatively easily, and am generally quite confident in myself, though I retain a healthy amount of self-doubt too.

Now, this woman and I have very clearly made a connection with one another (or at least that is my distinct impression, and I don't think this is a case of self-delusion). She is at once very shy at times, especially when I say something that is of a more personal nature, and she has gradually opened up to me about her feelings on various subjects (I'm not talking about deep dark secrets, but rather any area that might call on her to reveal something about herself or her feelings on a matter that is personal as opposed to work). My closest friend in the office has observed that this woman has clearly shown an attraction to me. The elevation in our friendship where all of this became apparent has taken place over the past couple of months. And I am extremely attracted to her-- my reaction to her has been stronger than with anyone I can remember in my past. The butterflies in my stomach have been working overtime.

There's a little more to report in the way of developments, but I've been going on and on, so let me save that for part 2. I seek your advice about how to deal with this situation. Believe me, I understand that a work relationship of this type cannot happen without one of us leaving the organization-- and I would be willing to go elsewhere in the name of love. I am a romantic. But how do I navigate this situation so that we can find out whether there is something truly sustainable here, to get to the point where we will have to decide how to arrange things at work if we find that we want to pursue a relationship?

Even though I go on (and on) I'm sure I've left stuff out, but let me stop here and beg for your feedback. Like I said, something more than "Don't do it period" would be welcome. Any insights on how she might be feeling given the age gap and work situation would help, and things I can do to be sensitive to the circumstances too. Thanks for listening everyone.

Here's part 2:

The other night I invited her out to coffee to talk. We found a night that worked for both of us. My objective: I thought if we talked a bit about our work circumstances it would help clarify things for both of us and maybe clear the path for us to let our relationship develp more. That's usually my approach: if there are issues I like to get them out on the table and discuss them.

Well, it turns out that seems to have been a mistake. She was nervous from the beginning because I think she thought it a bit odd that the big boss wanted to ask her out to talk. Beforehand she even asked me if she was in trouble. It didn't go well. I told her that I very much enjoyed talking with her and enjoyed her company, and that I wanted to keep enjoying her company, and that I wanted to make sure that our work circumstances didn't pose a barrier-- Like I said, I'm the head of the office and rumors tend to fly when you're in that visible a position. She seemed stiff and put up her defenses the entire conversation. I think I really blew it by taking what seemed like the direct approach to me. I feel like if I had just let things develop as they had been we could have continued to make progress. Now I sense that by calling attention to the situation I have scared her back into her shell, maybe for good.

I really, REALLY am attracted to her and think we have a lot going for us that would be worth exploring. Did I blow it? Is there anything to do next? Help.

what is the nature of your company? Are you sure you would have to leave if a relationship developed? I know that the office romance taboo, especially between supervisors and subordinates, is a big cliche, but I've worked in several companies where that is not necessarily the case. The company I currently work for, for example, has a husband/wife who are subordinate/immediate supervisor. Unusual thought it may be, it can happen.

Without knowing more details it's hard to comment further. The thing to say is what everybody usually says in a circumstance like this. Take your time, get to know her as friends and when you feel the time is appropriate then take it to the next level.

Honestly, I would lay low. You might make her feel like you are trying to scare her into liking you. It could be seen as sexual harassment, for all we know. I wouldn't try too hard and I would let things just flow together.
She is new to the office, so naturally she is at unease. She is still trying to figure out who everyone is, and to have the boss man do that, would be a definite shocker. Try not to make her feel at unease in the office.

Matt and I met at work. Although we are in different departments, I do at times have to work under him. We knew each other for 2 years before we started dating. I am also the daughter of the owner. So when my dad, the general manager, and my direct manager found out, all hell broke loose. There were meetings, both professional and personal. He was told to "end it now" and "it's not a good buisness decision" by managment. He was also chewed out on company property in front of other employees by my dad (owner). I would lay low and figure out if this relationship is worth the heartache and trouble. There may be a company policy that states employees cannot have personal relationships and one of you may have to look for another job, or it may be fine. Just make sure it's worth it. In the beginning I remember Matt and I in tears over the company "bullying" but for us, it was well worth it. If your not ready to fight, then you may want to think twice about persuing a relationship at this time.

Good luck to the both of you!

Christina

She was nervous from the beginning because I think she thought it a bit odd that the big boss wanted to ask her out to talk. Beforehand she even asked me if she was in trouble. It didn't go well. I told her that I very much enjoyed talking with her and enjoyed her company, and that I wanted to keep enjoying her company, and that I wanted to make sure that our work circumstances didn't pose a barrier-- Like I said, I'm the head of the office and rumors tend to fly when you're in that visible a position. She seemed stiff and put up her defenses the entire conversation.

You need to take a step back. To be completely honest, the ages here are fairly irrelevant but I am about her age, and if the big boss took an interest in me personally like that and I reacted the way she did... that would be a clear indication that it was making me very uncomfortable and that it needs to STOP. However, if I were interested, I don't really think the guy's position or the age difference would bother me. So from where I'm sitting, it sounds like you are making her uncomfortable and that she's not interested. I'm sorry to be so blunt. You are in a position of authority over her and you need to stop ASAP. Good luck.