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Your Call: Should He Hit on a Coworker?

Fri, Aug 5, 2011

Advice, Dear Em & Lo, Your Call

photo via Flickr

We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call by leaving your advice in the comments section below.

Dear Em & Lo,
I like this woman at work (she’s a coworker, not a boss or underling). I’d love to go out with her, I think we might be great together. I know she’s single, but I’m not sure how she feels about me. I don’t want to create any awkwardness at work, especially if she’s not into it, or even worse perhaps if we start dating and then down the road it doesn’t work out. Is it worth going for? And if so, how do I approach it delicately?
– Working Boy
What should WB do?
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7 Responses to “Your Call: Should He Hit on a Coworker?”

  1. Notmything Says:

    Hey Working Boy,

    It is worth pursuing. First of all are you the kind of guy who falls easily for someone? Does your heart go aflutter with any attractive woman that wanders within your personal space? If you feel that you would love to go out with her and you don’t feel that way with every woman, that is all you need to know. The rest of those vacillating/doubting feelings are coming from a place that isn’t going to serve you and only act as a vehicle for you to have similar feelings about the “next girl” and you will just repeat the same pattern of denying yourself or even worse, denying her a chance at getting to know someone great. So you might as well deal with that issue now right? I mean to say that it might not work out down the road is a common fallacy that most of us guys buy in to but it is an excuse and has no bearing on what is going on with her. So cut that out o.k?

    First of all I wouldn’t just ask her out, she might get defensive due to the work environment you are in. I would show an “active disinterest” in her since you are not sure how she feels. I would bring up that you are going to this interesting place. Don’t invite her (yet), just talk about how fun it is and really convey the emotion to her of you really liking it. If she doesn’t hint (on her own) that she would like to go with you, that is o.k. The next day after the event, reiterate to her the good time you had (be truthful and really go to place, because if you don’t she will sense it somehow and not trust you, woman who are worth getting to know are psychic that way). Mention that she popped in your mind while you were there, that you could envision her really liking it and next time you go, “you are definitely bringing her along.”

    What that conveys to her is that you are fun and thoughtful without you directly asking her out. Don’t ask her if she wants to go next time, you will put pressure on her. Just say she IS coming along. It will also show that you are confident and can make decisions. If she is interested in you at all she will go with you. If she declines and is interested in you, she will probably give you a good reason for it and recommend another time you two can hang out. If she hems and haws and declines politely, she probably isn’t interested in you but you will feel good that you honored yourself and broke a pattern of making excuses for not pursuing someone you are really drawn to.

    Good luck, I would love to hear how it went. Again, I wouldn’t recommend just asking her out directly though, since you are having trouble even getting up courage to do it, you will probably come across as awkward and you won’t convey the guy who you really are to her. Make it playful and convey to her she would be missing out on a fun time if she doesn’t come along. Once you are alone with her I am sure you will know what to do.

  2. anon Says:

    Go for it!
    Just don’t be creepy or pushy…
    Actually – a good angle would be to go on a few not-a-dates first, just sandwiches at lunch or something and see if you like hanging out. If you do, then suddenly you have a non-work context in which to ask her out. (And if you don’t, dating would have been awful anyway).

  3. Johnny Says:

    Don’t do it. If there was crazy chemistry and you were really really convinced you could make it happen, maybe. It’d still be a bad idea, but let’s face it – there’s no fighting crazy chemistry.

    But you’re “not sure how she feels” about you, which means you’d be going out on a limb. Work is not the place to go out on a limb.

    There are a bazillion women in the world who you could go for risk-free. Go for one of them instead.

  4. Johnny Says:

    ^ actually, let me modify my advice: if you’re a young person in a summer job, go for it. In fact, go for all the women you work with. Jobs like that are made for getting fired from.

    But if you’re a grown-up who takes his job seriously, or at least depends on the income, then don’t do it. It’s not worth it.

  5. Lily Says:

    It seems like you’re already stuck in some sort of analysis paralysis. If there is chemistry there you feel it. Or at least you would suspect it, even though we have a tendency to make shit up in case we are super hot for the person. I think that unless you are currently in a desperate phase of your life then you just KNOW. So trust your gut and just say the stuff – at the next work event, so you have a valid ‘ man waz I drunk’ excusein case the lady says no.

  6. Mikey Says:

    Approach her fool! To ensure maximum success use the following foolproof methods…
    1. Constantly talk in a loud voice that booms throughout the office about your “world of warcraft” stats.
    2. splash on ALOT of cologne – preferably “old Spice” or an Axe body spray.
    3. look her dead in the eye, and in your deepest, sexiest voice growl “Gurl you know you want dis.”
    4. offer her hard drugs
    5. hit on her friends in the office in order to “up your desirability quotient” in her eyes. Make her jealous, and she’ll come to you.

  7. Al Says:

    Real advice, don’t date co-workers. If she’s not interested at all it will make her feel awkward, and if she is you’ll catch on eventually. If you really think it could be serious one of you should find a new job, it is not worth the hassle and career damage just to date.


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