Stuck on my work crush

Another long letter ... and a holiday party ...

Hi Meredith,

I started working at my current job over three years ago. When I arrived, I met Sue. The attraction (on my end) was instantaneous. While I don't think it's all that important to this story or advice, I'm a bit older than Sue (I'm in my late 30s, she's in her late 20s). What is probably more relevant is that when we met, we were both in relationships. However, my relationship (of a few years) ended several months ago.

Over the past few years I've had the opportunity to get to know Sue as both a co-worker and a friend. My physical attraction to her has not gone away. She has all the qualities I look for in a partner -- from a great sense of humor to being intelligent, caring, selfless, generous, and kind. We've also shared some similar life experiences, some of which others cannot understand or empathize with.

After a holiday party two years ago, and after having some drinks with no food, both of us left and I asked if she wanted to grab some dinner before heading home. She acted awkward and said she couldn't. I felt it was strange, and after some prodding, I later learned that her bf was not all that high on me and for lack of a better word "forbade" her from hanging out with me outside of work. To this day I've never met him.

Sue and I went the next year with our work routine, and while I at times felt that maybe she had feelings for me, I would often dismiss the notion. So, at last year's holiday party, we again left together since we take the same T line. While the exact manner in which it was brought up is still cloudy, Sue started talking about why she couldn't hang out with me outside of work. While I had been operating under the assumption that it was because of her controlling bf, I learned it was partly because Sue had feelings for me. I was completely floored to learn this, and I know that she regretted letting the cat out of the bag.

Over the past year, I've learned more about her relationship and how unhappy she is. I know most readers would assume that I'm rooting for her relationship to fail so I have a shot with her, but I can honestly say that's not the case. If she was in a healthy, happy relationship, I'd be ecstatic for her as she truly deserves it. But she isn't.

Recently, I started going out on some dates and talked to her about one of the girls. She got weird and when I pressed her on it the next day, she conceded that it made her jealous (though she also said she had no right to be that way and apologized). So, clearly her feelings extend beyond friendship, as well.
Over the years, there have been times where we've come to the conclusion we cannot be friends. For example, she sat me down at lunch awhile back and told me she had to end our friendship because she felt she needed to try and salvage her relationship, and part of that was respecting her bf's wish/order that she not be friends with me. That lasted about three days before she came and told me she couldn't do it. Likewise, I've tried to end the friendship because I couldn't deal with how strong my feelings were. However, as many times as we've tried that route, we keep going back to being friends because I think there's an undeniable bond between us.

I'm lost as to how to handle this situation. We've tried to pull back from our friendship to more of the typical co-worker scene, but that has not worked for either of us. While I know it's more complicated, sometimes I just see it as a simple equation: she's unhappy, she has feelings for me, I have feelings for her, break up with him and let's see where things lead. But I'm a realist and I don’t think that’s going to happen (and I guess there's no guarantee that even if she was single that she'd want to date me). Since I wasn't in the happiest of relationships previously, I thought that perhaps dating again would take my mind off my feelings and allow me to move on. However, I end up comparing these new girls to her and I still find myself thinking about her constantly. The prospect of losing her in my life is a miserable one, but since we've tried most options, is the only solution for me to find another job and cut all ties with her?

– PossibleJobSeeker, Waltham

If you're open to finding a new job, apply elsewhere. It sounds like you could use some new scenery in more ways than one.

But if you love your job, don't quit because of her. Just make sure that you're being honest -- with her and yourself. You mention that you ended your relationship a few months ago ... but you've had feelings for Sue for years. Does Sue understand that your feelings are legit?

If Sue does understand how you feel, you need to focus on reality and allow yourself to get annoyed. You say that she has all of the qualities you look for in a partner, but I'd argue that she's missing a few. She's not single, she doesn't sound very self-aware, and she's not supporting your efforts to be happy. When you mentioned dating, she couldn't get behind it. All she did was remind you that she wants you for herself. That's annoying.

My advice is the advice you've already given yourself. Be clear about your intentions, set boundaries, limit the interaction, and date as much as you can. I know you've already tried all of this, but try harder.

I assume that you're about to attend another epic holiday party. When you get home from this year's event, think about how you feel. If you're sad and irritated that you wound up by yourself at the end of the night, focus on those feelings. Use them to help you enforce the rules. Think about what's possible, not what you hope will eventually happen.

Readers? Should the LW get a new job? What about the recent breakup? Should he be honest with her about what he wants? Should the LW be with anyone right now? Should he just let this go? Help.

– Meredith