Dating My Boss: Can This Work?

 By Nina Atwood

Steve writes: I have a dilemma. I recently bumped into my boss at an engagement party. We drank wine, talked, flirted, and kissed a little afterwards. I asked her out the following week and she accepted. We went out, drank some wine, had a great time, flirted and kissed again. When I dropped her off, she said we couldn’t date because of our professional relationship, saying she didn’t want to get in trouble at work. Since then, she will talk but won’t initiate a call back to me. I feel like I’m getting mixed signals. I’d like to date her but I’m confused. What should I do?

Dear Steve: First you must gain clarity about some things. One, if you didn’t work together, would she want to date you? Two, is she available? Maybe she’s dating someone else. Three, what are the consequences at work if you do date (i.e., someone loses their job)?

Mixed signals are usually a result of ambivalence, meaning that she feels one way about dating you but she also feels another way. Half of her is attracted to you and wants to see where it could go, the other half doesn’t want to lose her job/status/current boyfriend or whatever it is that she fears losing. Your job is to ferret out the real issue in a non-threatening way. Here’s what I suggest.

Call her again and lead into the conversation with something like this: “I just want you to know that I really had a good time when we met at the party and later when we went out together. I would really like to go out with you more and see where our relationship could lead, but I’m not sure it’s a good idea based on how much you’ve backed off. It would really help me if you could just tell me straight out what the issue is. You won’t hurt my feelings, I’m a big boy. But I need to know if our work circumstance is the only thing in the way, or if you’re dating someone else, or just not interested.”

Once you raise it like this, the next step is to close your mouth and listen. If she has it in her to be forthcoming, she will. You then have the opportunity to hear what she says, maybe ask a clarifying question or two, and then accept what you hear. If she says it’s really work, then ask this question: “If I were to change the situation, such as by asking for a transfer to another department, would that open the door for us to date?” If she tells you not to do that, you have your answer: it’s not about work, it’s about her low level of interest. I know it’s confusing, but people sometimes enjoy a little flirting and kissing because it makes them feel attractive and desirable, but it doesn’t necessarily mean they want a relationship.

If she refuses to open up and clear the air, you also have an answer: this relationship isn’t worth it to her to bother to be honest and open. What you are looking for, Steve, is evidence that she’s geunuinely interested in you. If you find that evidence, great! The way is now clear for you to move forward, pursue, and see how far this relationship can go.

If you don’t find that evidence, let go and move on. The worst thing you can do is continue to pursue a woman who doesn’t want to be pursued, espcially when she’s your boss.

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1 Comment

  • 1. Steve Flores  |  July 5th, 2007 at 11:36 pm

    Dear Nina,

    Thank you for the awesome advice. As luck would have it, I went out of town for two weeks to attend mantadory work training. I just got back to the office on July 5th. I will take your advice and have the conversation next Monday or Tuesday. Thank you again, what you suggest makes so much sense!



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