How should I proceed with this confusing crush?
November 1, 2013 7:03 AM Subscribe
What should you do when it would be inappropriate to be romantically involved with someone, yet the attraction between you is so strong it feels like the relationship is gathering momentum and heading towards the inevitable?
I have a professional relationship with a man (let's call him James). He's in his late thirties and I'm a girl in my early-mid twenties. I am almost certain he is romantically interested in me. We email all the time and get on really well. He is always lending me some book/CD/DVD he'll think I'll like, he's always eager to help me with stuff, he sits really close to me and his friends say he speaks very highly of me. The problem is, I think he's quite depressed: he's always extremely emotionally guarded and seems to have very little self-confidence. As a result I don't really know much about his life at all, other than his interests and specific things I've asked him directly. Lately I've found myself thinking about him all the time, wondering what he's thinking and wondering if something could happen between us.
The reason why this crush is especially confusing is that I recently broke up with my long-term boyfriend. My interest in James was sparked before my relationship ended (and probably contributed to my wanting to break-up) and has just intensified now that I'm single and missing the comfort and reassurance of a boyfriend.
I don't want a serious relationship with James for a number of reasons: a) I just got out of one and would like to be independent for a while, b) I don't think I could emotionally support someone who is depressed at this point in my life c) it would end our professional relationship (he is a client of mine, and I receive regular payments from him) and d) I am unsure about my feelings for him and don't want to hurt him by acting on my attraction and then pulling away if/when I change my mind.
I am certainly attracted to him and would like to form some sort of intimate emotional/physical connection with him. I just think there would be a significant disparity between my fantasy and the reality of what it would be like to be with him. Having said all that, I am crushing hard, and I can't stop myself from flirting and teasing and wanting to get physically close to him.
He hasn't asked me out, but I think he's being cautious and is afraid of rejection (I am sort of in a position of power to him). I also think he's intimidated by me, as I appear confident and I seem to have a lot going for me, while he seems incredibly anxious all the time (except for a few moments where I've managed to make him smile/laugh/relax). I generally always encourage his attempts to get closer to me, and I think that if I tried to backpedal now it would seem as if I've been stringing him along.
I definitely want something to happen between us (maybe even just sexually), even though I know it would probably end badly. I find his caginess mysterious and attractive, and part of me wants to be the girl that could bring some more light into his life (without having to deal with all the dark stuff). The fact that he's older and totally not my usual 'type' makes me want him more. I think we could have fun together and I would genuinely like to get to know him better, though sometimes I wonder if I'm just at a weird transitional point in my life where I want to be reckless and irresponsible.
Has anyone else been in this kind of situation before? Is so, how did you proceed?