Single male boss flirts with me but then turns cold whenever I show that I am clearly interested. What do I do?

This has been going on for nearly 2 years now. We are both single (Well I'm divorced and he says it's been over). We share a small office. It's obvious to every one that we really like each other a lot. We've felt each other out about the age difference (we have a good 20 year age difference). We are constantly flirting and joking around or showing off for each other. I've dropped a few hints of my serious interest, But when my co-workers ask him why he won't ask me out he says that he doesn't date the people he works with... Even though he has brought up married working couples running a business.

How do I get him to stop flirting without hurting his feelings or ruining our work relationship since I have to share a small office and work directly with him? Or am I just doomed to needing to find a different job? (not necessarily with the aim to date, but because this situation is emotionally draining and agonizing the way that it is).


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What Guys Said 2

  • You should tell him, "I need to talk to you seriously. We have BOTH been flirting back and forth for a long time now, to the point that everyone is aware of it. I find you attractive and I'd like you to take me out. The problem is, if you don't want to take me out, then you need to stop leading me on because its making me miserable to the point that I'm thinking of leaving"

  • This is a common subject. People always ask questions about getting together with co-workers, or even worse, Bosses.

    This is a terrible idea.


    Because, everyone will talk about this. No, you cannot keep it a secret. Everyone knows "who's doing who". People can see the subtle looks, body language, etc. People will talk about you, in some cases, negatively, because they know it isn't cool.

    If the 2 parties are overt in their relationship, it creates a nonprofessional environment, which can lead to difficulties with the bosses.

    If it IS a boss, then problems with the next level of management may occur. Rumors are worse. "Look who's sleeping themselves upward".. on and on.

    THEN, if the relationship fails. What then? Well, the talk gets worse. The two parties themselves may talk poorly about the other person. Rumors are started. True or false, a bad environment ensues.

    Nothing good becomes of this.

    • I think the whole "How do I get him to stop flirting..." bit denotes I'm past that part.

What Girls Said 1

  • I can understand his reaction especially as he is the boss. I would ask him directly and get it from the horses's mouth so to speak. I would stop flirting with him, being playful with him and just keep it a strictly professional relationship. The reason, you need to see if you can tempt him into doing something to get a relationship going. Also, it may be enough for him to flirt with you so as long as he has that he does not need to proceed into starting a relationship. I would find the courage and speak to him directly.