Your Call: Should He Hit on a Coworker?

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

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Barbara Arthur
Response from a middle-aged female who used to work in career-oriented management positions but now chooses to work “just a regular job” because she thinks management jobs suck (so thinks she can offer various perspectives): Not enough information to make a well considered response, so I’ll respond with questions then answers based on those questions. Does the company where you’re employed have any policy prohibiting dating coworkers? If yes, and you want to keep your job, don’t ask her out. You’ll jeopardize your position–and even, possibly, hers, even though she’s simply an innocent bystander. Management in some companies are real… Read more »

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.


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.


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.


^ 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.


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.


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).