Your Call: Should He Hit on a Coworker?

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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 Comments on "Your Call: Should He Hit on a Coworker?"

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4 years 5 months ago

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.

4 years 5 months ago

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.

4 years 6 months ago

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.

4 years 6 months ago

^ 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.

4 years 6 months ago

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 years 6 months ago

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).

4 years 6 months ago

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… Read more »