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I really need your advice on this one! How can I get her to open up about her feelings towards me?

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Question - (12 July 2009) 4 Answers - (Newest, 13 July 2009)
A male United States age 51-59, anonymous writes:

I apologize for the long post, but I feel that I’m experiencing a dilemma that requires some sort of a resolution.

About three years ago I became the supervisor of a woman whom I found to be full of contradictions. (Currently I’m 43 and she is 39.) She was easy to deal with in work situations, yet revealed nothing about herself. She also, at least to me, came across as rather sweet, but as someone with a foreboding aura about herself.

We became friendly and starting talking on a regular basis. The conversations, however, seldom veered into personal topics. She must have heard from others that I have a live-in girlfriend, and that our relationship was somewhat on shaky ground. Sometime later I found out that she (my coworker) had started seeing a guy regularly.

While our conversations never delved into our private lives, I thought that my coworker’s body language suggested that she was attracted to me: she continuously ran her fingers through her hair, touched me occasionally, etc.

We had 3 or 4 lunches together and the pattern continued: lots of body language suggesting attraction, but few words indicating any interest. The conversation never exactly flowed and she never asked me anything about my past or interests. She kept on asking on a continuous basis, though, about my weekend plans. On a few occasions, when we both were complaining about our jobs, she commented that we were at least lucky to have met each other. When I told her that I wanted to find another job, she replied that I would be leaving her alone or something to that effect.

I concluded that this woman must have suffered some sort of emotional trauma and didn’t have the willingness or the skills to elevate the flirting to a higher level. As to the body language suggesting attraction, I attributed that either she was doing it subconsciously, or simply was yanking my chain and was craving attention. I also found her contradictory behavior somewhat emotionally taxing.

While I was sexually attracted to her, I wasn’t exactly drawn to her personality: I sensed that there was something neurotic and codependent about her. So I acted warmly but rather aloof. And I was always nice to her and complemented her regularly.

Sometime later I was assigned a new job (I no longer supervise her), in a different department and on a different floor of the building. I decided to not to go to lunches any longer and minimize my contacts with her. She kept visiting me regularly--whenever she had business on my floor-- and on my birthday brought me a slice of cake (with another female coworker). Since I hadn’t told her about my birthday, I can only assume that she must have looked me up in the system.

A couple of months ago we found out that she and I would be attending a 90- day training class together. Before the class started, she visited me twice and suggested that we seat together in the class.

So we started going to this class and seating next to each other. She opened up a little and told me that in her early twenties she had been in a five-year relationship and her boyfriend had unexpectedly left her. She took it so hard that she stopped dating for a long time. Now she is with this guy, they usually meet on weekends, have gone on several trips together, although the topic of marriage has never come up. I assume that the topic of marriage hasn’t been brought up by the boyfriend, since she told me that she wants to try marriage “at least once”, and also sensed that she wants to be on the good side of the boyfriend’s mother (the boyfriend lives with his mother).

I called in sick one day and when I returned she kept repeating how much she had missed me and how lonely she had felt. She also often kept asking me where I had gone to lunch. She demonstrates the same body language, in addition of seating rather close to me.

So I found myself in the same psychically challenging situation as before: is this woman trying to tell me that she cares about me or is this some kind of a dysfunctional/manipulative game on her part?

In short, if her interest in me is genuine, I would like to provide an acknowledgement and appreciation for her feelings. Then I would like to end the tension and tell her that while she and I are currently tied up with someone else, should it so happen that both of us are free, we should get together and give it a go. In essence, I’m looking for a thank-you-maybe-later-when-things-are-more-clear approach. This, I’m hoping, would acknowledge that 1) I’m reciprocating her feelings toward me, 2) boost her self esteem, 3) end the whole thing on a happy note.

I’m not exactly sure how to get her to reveal her true feelings toward me, though. I tried humor and she became very cagey and confessed that she plays it close to the vest. If I ask her straightforwardly whether she is interested in me she might panic, and attribute this to a huge misunderstanding on my part.

I can directly ask her out, of course, but I’m not ready for a steady relationship with her. It is clear to me that what she is looking for is a steady relationship ultimately resulting in marriage, and I don’t think my entering into her life – without serious commitments on my part – would be emotionally healthy for her.

So there is palpable tension between us and for some reason this is taking a toll on me. I could, of course, move on without broaching the subject. But somehow I feel that I have to talk to her, yet I don’t exactly know how.

View related questions: co-worker, flirt, move on, self esteem

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A reader, anonymous, writes (13 July 2009):

What an interesting question. You seem a good conoisseur of human nature and motives. So you are attracted to this woman but more sexually than otherwise and confused by her behaviour that is somewhat unconsistent. Well, relationships with emotionally troubled people can be quite challenging and mean a lot of work and energy spent, which obviously don't always give the desired results. It does seem she is a difficult person, who knows if she can open up later on...

For now, I think starting a potential relationship is by the wrong leg foremost, when you are not quite attracted to her personality, since she has let little to be seen concretely with all the mixed messages in the way. Try to get her to lower her guard perhaps a little more and reveal herself more as a human with wishes, thoughts on life and relationships etc, maybe you can discuss about these while you are deciding if you have compatible views and/or are fit for one another, if she would handle the challenge?... at your age it would be somewhat ridiculous to prolongue this type of situation forever, deciding whether or not to date. So try to guide her in the areas of conversation that interest you and see how that can help you make up your mind about whether or not it is wise to get involved, and know at once what to do next. Best wishes.

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A male reader, Your friend Australia +, writes (13 July 2009):

Your friend agony auntWhat a story. In your 2nd last paragraph you mentioned that she is looking for a steady relationship and ultimately marriage and that a relationship with her would not be emotionally healthy for her. If you know this is the case and not prepared to be part of such a relationship then you have your answer. There is nothing else for you to do but sit next to her at the course and be nice. Finally you mentioned that you had to talk to her, given my comments above I'm not sure why.

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A reader, anonymous, writes (13 July 2009):

An extremely well written post. This is an extremely exhausting situation and one I have a great deal of experience with. I too worked on a daily basis with a man for 13 years and we regularly had lunch, chatted talked etc etc and I could feel there was an interest but it never really came to the fore. We both were with other partners. I too wanted to say that if things were different I would be interested but I always held back as I felt i might put him off or that I had read the situation wrong. Consequently I did nothing. These lunches and flirting continued for years and years with him enginerring to come to my office over nothing and banging into each other at the coffee machine etc etc. I felt emotionally worn down by it all. Eventually I left the company and he regularly called on his mobile and we still met for lunch. I turned into his confidante but with this underlying feeling of more hidden behind the facade. It is still like this so I have no answers and being old school female I felt unable to take the lead.

Without fail this woman is extremely interested in you and is looking for more. She is obviously totally unable to express her emotions but really wants to take it further. I think if you are interested that you are going to have to be the dominant party here and take the lead asking her if she would like to go out even if she rebuffs you or behaves strangely. This is the only way you are going to get any closure on this. To continue as you are is just too mentally exhausting and I think you need to accept that you have to do something and get a result one way or the other. My gut reaction is that she will be keen to go out with you. If she isn't just put it down to experience and behave as normally as you can when you see her or she seeks you out. She clearly has deep seated insecurities but I am sure she is very keen as this wouldn't have gone on for so long if she wasn't.

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A female reader, newbern United Kingdom +, writes (13 July 2009):

Quite an interesting situation, I don't deny.

I feel for you because there is a category of people who are incredibly difficult to read and send mixed signals.

It could be that she's just a 'natural flirt' and she enjoys your company as a friend.

Or, on the other side, she may be gagging for you to make a move. Trouble is, if you do and it turns out you misread the whole thing then it's going to be double embarrassing.

Maybe you could try an out-of-work evening, like a work do with other colleagues and see how she acts outside a work context, maybe with a drink or two?

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