Is my boss into me? How can I get him to ask me out?
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Thread: Is my boss into me? How can I get him to ask me out?

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    Is my boss into me? How can I get him to ask me out?

    I've been infatuated with my super hot manager at work for the past few months after I started my new job. He is in his mid 30s and I'm in my late 20s. He is my direct supervisor but we work on different floors, so we don't interact everyday. He seems to be single, or at least not married as no ring is present and there was no mention of a wife from him or other coworkers, but I'm not 100% sure. I am single. Anyway, it began with subtle hints of attraction. In the beginning, he would go out of his way to bump into me on my floor, which I knew because he would come down for trivial reasons like getting supplies or talking to a worker that is in a different department, and look for me to wave and smile. Whenever I did happen to sit down and have a conversation with him about work relates issues, he always paid attention to every little thing I said and he would remember all the details the next time I spoke to him. Also, I generally thank him and show my appreciation for everything he does to help me and compliment him, and he seems extremely flattered and moved every time, with smiles. Sometimes, when I bump into him, he seems startled and speaks in a lower voice. Other times, he tries to act cool and casual but I can tell his mood changes after he sees me. We've never went out for lunch or anything yet, because of our different work shifts and the overall office environment is extremely formal and nobody goes out to eat together. But outside of work, he always finds a reason to call me about some work related issue.

    I thought he was just being friendly because he's generally nice to everyone (but not flirty. He is very professional) but recently he had been calling me into his office on his floor more often for one on one meetings, and he would offer me certain projects saying that he could've given them to other workers but he chose to give them to me first because he wanted to help me. He also said I can call him anytime even if it's late at night if I need to ask for any further help. Our meetings have progressed to where he was just polite and professional to him trying to crack a small joke here and there and asking me about my personal/career life. He has yet to tell me much about his own personal life, but then again, he is the slightly guarded type and we are in a very professional corporate environment. He does, however, drop little things here and there about himself.

    My gut feeling tells me he is into me too or at least somewhat attracted to me, but I'm just not 100% sure. I'm quite the blunt and honest type, so though I do speak formally because of my work environment, I also talk a lot about my life or whatever issue at work freely. He seems to enjoy listening to me talk, because he always says I should stop by his office to talk whenever I want, but I'm not sure if he was just being friendly or he truly wants me to be around.

    From these actions, does it seem like he is into me?
    I would really like for him to ask me out, or to at least become closer and know more about his personal life, but I don't know how to progress. We are in an industry where it takes a lot of time and experience to move up the ranks, so I know he wouldn't want to risk losing his job, nor do I, though I do not plan on staying at this company long term. I'm finding it difficult to let go of the infatuation. What should I do?

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  3. #2
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    Office relationship is a slippery slope, especially if it's a boss. If you guys do end up dating, his supervisor would most likely reorganize the org chart. I would advise against starting a relationship with your boss if at all possible.

    As far as getting closer to him: Take up his offer and give him a call at night. You can begin it with project conversation, but see what progresses from there.

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    Would it be tolerable to keep doing what you two are doing to not put your jobs in jeopardy and to gather more information to see what he's up to?
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