Guys, I Need Help?

ok so i just started this new job and I kinda like my boss. He is new to the state and doesn't have anyone to really hang out with. He is hard for me to read. I am just getting back into the dating world after 7 years. Ok so one of our co workers lives right across the street from him and our boss wants to hang out with me, our co worker and her husband. I dont know what it is but I think he likes me and I want to make the first move but I dont know I just am not sure yet. He will flirt with me and come up behind me and play with me hair or like when we have meetings i always catch him looking at me. Its funny and kinda cute how he like flirts with me because its kinda like the little things that guys do when you're in grade school. He caught me off gaurd one day when he said something to me, i didn't hear what he said, and then he winked at me and the whole wink threw me off gaurd. Today he was leaving work early and before he left he blew me a kiss goodbye. Any guys out there who may act like that when you like a girl?


Most Helpful Guy

  • It sounds like he is head over heels. Especially our agegroup. We don't act like that towards girls we are not interested in, especially in a professional environment.

    You could safely ask him out, I think, without really worrying about rejection. If he says he is busy, he probably really is, so have a few time slots to choose from.

    I might also warn about the dangers of in-office relationships. I am sure you know all about that. But I'm just answering the question here :)

    • Yea I am aware of the dangers of in-office relationships. I know how to keep my personal business my personal business

    • Hopefully he'll keep your personal business as your personal business as well.

      You hope you two have an amazing experience together.

    • *I hope you two

      bleah typos. You go girl!

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What Guys Said 4

  • Are you willing to risk your job?
    if you are
    Yeah make a move on him after you meet up with your friends/coworkers and when you guys split up after dinner pull him aside lol

    • If I keep my business to myself than i wouldn't have to risk anything..
      I dont even know how he truly feels but even if he didn't like me i wouldn't lose a nights sleep over it.
      and of course i would pull him aside... I am not new to this Thank you

  • message me, I can give a good example of why you don't date your boss...

  • Of course it is up to you... but I own my company and would never date a co-worker.

    There are just too many potential legal issues, if it ever went wrong.

    You mentioned a co-worker above... my worry would be if I allowed a girl at the office to become my gf... how would that affect my relationship with my other employees? Would they be constantly thinking behind my back that I am favouring the staff member that I am seeing.

    Even though you two may not have an issue with it... it puts him in a terrible position that could backfire regardless of how happy the two of you are.

    So I guess what I am saying is you have to look at it from all perspectives.

    People can become petty... so you have to consider that some of the other co-workers may think that you flirt with the boss for advancement. Even though there is no word of truth to it... people will be people!

    To me it is just not worth the risk.

  • Never date your boss...


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