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?


  1. 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 assholes and don’t listen to reason, no matter how clear reason is. If no policy prohibiting–well, it depends. Let’s keep going…

    Are you a job person or a career person? In either case, is it a permanent job you’re attached to or a career-oriented position that you are either attached to or could lead to even better positions? If so, don’t ask her out. Now, if it’s “just a job,” you’re not that attached to it–well, it depends. Let’s keep going…

    Just how attracted to/into her *are* you? Other commenters are right–there are “other fish in the sea.” Sorta. Frankly, your odds relate to what kind of catch you are, and we don’t know you. Plus, even if you’re the greatest catch, those fish aren’t always so easy to find if you’re working all the time! That’s a big reason why there are so many workplace romances. Thing is–what you said about making things awkward if she says no–or things being even more awkward if she says yes and things don’t work out…well, totally correct. Stuff of workplace legend there. Granted, you’re into her enough to ask the question here. But how seriously have you thought about this *yourself*? You’d better be interested in her enough to be wanting a pretty serious relationship if you’re considering asking a coworker out–or just forget it.

    Tired of reading yet? Then you’re not serious enough about her. Don’t ask her out. Wanna keep reading? OK–here we go!

    Now, if you *are* serious about your intentions–what about the you-can’t-tell-if-she’s-into-*you* thing. There’s a couple of ways to find out. Subtly. That’s key. You need to do your groundwork. You can do it yourself, but not recommended. If you have to do it yourself, it’s pretty simple. Talk to her. Does she ask you questions about yourself? Your interests, what you’re doing over the weekend, about your family, your dog, anything? Those are all signs of interest and possible attraction. If, after striking up a couple of conversations, does she approach you to talk about anything, ask you for help with anything? That’s a good sign. Does she flip her hair when talking with you? Or–a biggie–does she touch you in any way…a tap on the shoulder, slapping your arm when laughing–any kind of touching is a sign of attraction. Nothing’s guaranteed, but positive feedback with those things ups your odds and gives more assurance of a “yes” when being asked out.

    But what you really need is a wing man/gal. Have someone else talk to her about you. ***Do NOT have them ask her if she likes you!**** NO!!! Simply have them talk to her–starting to talk about something *completely* different, then casually bring you into the conversation–and see what her reaction is. First, simply have them note her reaction to your name being mentioned. Have them pay *close* attention to that. Does she seem to have a positive reaction, neutral, flat, negative? Even no reaction is a reaction (although not a good sign). Then, have the person say something positive about you–and have them pay attention to her reaction about that (same thing–positive, neutral, flat, negative). Then–maybe–this takes talent…and is only necessary if the person hasn’t been able to figure anything out yet…have them mention something just a tiny bit negative. But do it in a really offhanded, and best of all, humorous way. (For instance: “Did you see when he bumped into the wall and spilled his coffee? Cracked me up!” Does she seem surprised or even possibly defend you? (For instance: surprised: “Gee, anyone could do that.” or, even better, defending: “I’ve done that before; it hurt!” or “That’s kinda mean; anyone could do that.”) That’s a really good sign. But if she agrees or even shares her own negativity, well, that’s a big red flag–but it’s good to know right off the bat than continue to wonder or to pursue something that’s a no-go. Anyway, I think you get the idea. Understand: this all needs to be done subtly, all woven into a very casual conversation, not at all like an interrogation! But a good wing man/gal can be your greatest asset in a situation such as this, and not to be sexist, but a woman works particularly well. Women dish about guys all the time. So, while a guy can do this for ya, if you can get a gal pal to, she may well be able to get a lot further…she may even get to the like/dont like territory…but *only* if the object of your interest goes there *first.* If she finds out that your wing guy/gal has been scoping her out for you, she may be flattered–or she may be creeped out.

    People warn about workplace romances all the time. Thing is, people meet at work all the time, too–and many a happy relationships spring from that! One of my favorite stories from the place I’ve worked the last couple of decades is that my friend laughing–a lot–that people keep gossiping, often not very nicely, about how (names changed) “Sally and Dave sure seem to go out to lunch together a lot.” My friend is “Sally.” Sally and Dave met at work–years before I started there. They got married. People don’t even seem to notice they have the same last name!

    So, here’s the bottom line: just how important is this woman to you, and what’s your priority–your life or your job? You leave your job and go home–and home is where your relationship is. Companies will have policies. Dating within the workplace will have pitfalls–and possibilities. Other employees will have attitudes (and will gossip; it comes with the territory). So–how important *is* this woman to you? Once you know that, you’ll know whether to ask her out.

    And once you figure that out, ask her or another woman out, she says yes, and a relationship develops, just don’t be a self-absorbed dick. And don’t tolerate a self-absorbed bitch. But that’s a whole different topic.

    Good luck!

  2. 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.

  3. 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. 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.

  5. ^ 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.

  6. 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.

  7. 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).

  8. 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.

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