How Do I Pick Up My Boss?

Discussion in 'Relationships, Discrimination, and Jealousy' started by xHotxSexinessx, Nov 3, 2011.

  1. xHotxSexinessx

    xHotxSexinessx New Member

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    I have this old boss, who I find EXTREMELY attractive, and I am wondering what's the best way to hook up with him. I haven't really had a good conversation with him in at least 2 years, but I have had a "crush on" (more like lust for) him for a long time. I also believe that he is straight.

    I really need help because I am socially awkward and I'd really appreciate some advice as how to approach then proposition him.

    Thanks.
     
  2. Draconis71

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    With all lifting, it's suggested to bend at the knees...

    Not too sure, tho, but, if he's straight... Might not be possible.
     
  3. dolfette

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    if you value your job, don't.
    there's just too many car crash scenarios to list.
    ''don't shit on your own doorstep'' springs to mind.
     
  4. xHotxSexinessx

    xHotxSexinessx New Member

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    I don't work for him anymore.
     
  5. crescendo69

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    Three things against you here:

    1. It's your boss - inappropriate
    2. He's probably straight - again inappropriate
    3. You are socially awkward; this can be overcome, but choose a better target for your affections.

    Oops, just read your last post. Good luck converting him.
     
  6. pinkpineapples

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    I'm not very good at the social thing, but here it goes. You could contact him, or 'bump' into him, wherever he works now... Make small talk, tell him it would be cool to hang out now that you're not in a conflict of interest scenario anymore lol and just kind of feel him out, straight vs gay wise...

    Like I said, I'm not good at this stuff, and I would never follow it myself lol, but its what came to mind. Good luck
     
  7. Cheetoo994

    Cheetoo994 New Member

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    I echo what others have already said... DON'T SHIT ON YOUR DOORSTEP.

    Never a good idea to date or hookup with a coworker, even worse to do it w someone who has the authority to fire you.

    Course you said "old boss." Still...keep that guy as a reference, don't screw up a decent recommendation chance.

    Anyway, good luck :)
     
  8. houtx48

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    something about getting your meat and bread at the same place...................
     
  9. Gamm

    Gamm New Member

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    If you value the friendship as is, then no. If you want to play roulette... well you know how that goes.
     
  10. flawdatiger

    flawdatiger Member

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    You said that you don't work for him anymore. In that case, go for it. Nothing ventured nothing gained. Hopefully he is old enough to have some maturity about it in case he is str8.

    Best case scenario is "flattered but not interested"

    Second best case is that you guys bang each other and it pleases you

    Third best case is that you guys bang each other and start to date, I call this third because the age difference will be a stone in your relationship river.
     
  11. Bbucko

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    Lots of times people say old when they mean former; I know I have.

    To the OP: if you no longer work in a situation where he'd have any jurisdiction over you, proceed with caution. You and he have very few degrees of separation, which means he knows the same people you know. That can lead to an awkward moment (or fifty) should things not go for the best (and really: when do they?).

    No offense to Dolfette, but fuck the doorstep. I first heard the expression as "even a dog knows not to shit where it eats".
     
  12. D_Bob_Crotchitch

    D_Bob_Crotchitch New Member

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    In Texas, it is simply, "Don't shit where ya eat.".
     
  13. helgaleena

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    I would not chance this until you no longer work for the same company! But if you are still in the same industry, it's still a risk! Try to get a crush on somebody in another profession; it's far safer.
     
  14. flawdatiger

    flawdatiger Member

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    I agree here. It's not going to be good if you have any important anything in common. So choose wisely.

    My bad, I knew in my head old boss didn't mean age, then forgot it as I was writing.
     
  15. arktrucker

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    Heres something that might put it in prospective: 'Don't shit where you eat'
     
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