The New Intimacy

Should He Hit on a Coworker? - from Em and Lo

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Contributor: Em & Lo Em & Lo
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?
08/10/2011
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Contributor: Ansley Ansley
I think he should invite her out to lunch and see how things go. Lunch is kind of a no pressure situation and maybe he shouldn't even hint at his romantic interest in her, but just see how they get along outside of the office just the two of them.
08/10/2011
Contributor: Peggi Peggi
Quote:
Originally posted by Em & Lo
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 ... more
I think he should try talking to her in the work setting first, feel the situation out a bit and see if he can figure out how she feels based on conversation. Casual conversation for a few days, followed by things such as "so, do you have any plans for this weekend?" or on a monday, "what did you do this weekend" can be good indicators based on her reactions. It would also give him a chance to see if she seems interested in talking to him, or just blows him off.

I agree, he could invite her out for coffee, or find a reason to meet up with her somewhere and just see how it goes
08/17/2011
Contributor: K101 K101
If youre both single I say go for it! To pass up the chance of an awesome relationship wouldnt be worth it. I say take it slow, make subtle hints to see if she probably returns the feelings. Try bringing her coffee, thats always a good hint. Just give her a little extra attention and youll more than likely get some sort of vibe, body language that says green light or red light or maybe uncomfortable yellow light! Its absolutely worth a shot.
08/31/2011
Contributor: Haiku Haiku
Generally speaking I think it is better not to date someone you work with, on the other hand, I've been there when the chemistry between us was too much to ignore.

Start with something light that could be taken either way: you want to get to know her better, take her to coffee or out to lunch. That way you can both assess teh chemistry and either flirt if it looks promising or keep it friendly and professional if the spark isn't there. Working with someone you have no interest in, knowing they wanted to date you, is a lot more awkward than working with someone you are seeing.

And for heavens sake, check your HR policy and make sure you aren't risking your jobs or promotions if you do decide to date!
08/31/2011