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So I've recently started a job and there is this female co-worker that I really like. I would really like to ask her out, sooner rather than later. However there is one big problem: We're going on a business trip, just the two of us, after 3 weeks of starting work and I wouldn't want to ask her out beforehand, potentially get rejected and then just create unnecessary tension during the business trip. Bear in mind that we would have to travel together.

Is it best that I just wait after the business trip to ask her out even if we would have already worked around 4 weeks together?

P.S. I do not care about the outcome, if I get rejected I'll just tell her that'll it'll not compromise our working relationship, but that I'd prefer not to be "just friends" either as I don't tend to be friends with woman that I'm attracted to. (Edit: On further reflection this is in fact a really bad thing to say, instead I would say, "We should keep this relationship strictly professional", if I do in fact get rejected.)

Edit: It's in the UK and her position is temporary (for 1 year), whilst I'm there permanently. Just for some extra context.

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    This could really do with some country information because this is going to vary widly by location and culture. Commented Aug 24, 2022 at 19:03

11 Answers 11

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I met my wife at work. I asked her out at work.

Rule #1: Don't be a creep.

If you are polite and ask for something low-pressure like coffee or an after-work beer it shouldn't be a problem.

Rule #2: Handle rejection with grace.

If she declines or deflects, it's a no. Say you understand and harbor no ill feelings. Move on and treat her like the professionals you both are.

Rule #3: Give her an easy out.

Do not corner her before or during the business trip. If she's interested in you, waiting until you are back won't hurt your chances.

Millions of other married and long-term couples meet at work since it's the place adults spend the majority of their time with other adults. Your workplace isn't a pickup spot, but if you are very sure you are getting positive signals from her, it's generally acceptable in America to ask once and only once.

Edit: There are so many other great answers and perspectives here. Please take the time to read them all, since this is a touchy subject.

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P.S. I do not care about the outcome, if I get rejected I'll just tell her that'll it'll not compromise our working relationship,

That's not how these things work.

Check during the business trip if there's some spark between you two. Don't try to push your luck, and keep the ambiguity up so that both of you have an easy out. If there's a spark and only then, ask her out at the very end of the business trip, just before you part ways. Again, ask in a way that leaves it unclear what exactly you are after. Something like "that was fun. Hey, since we both like Jazz, how about we go to (local Jazz club) on Friday, I saw that (some band) plays there."

Basically, make plausible deniability an option, so that you can both tell yourself that there was nothing romantic and you didn't actually hit on her, just thought about a shared interest with a co-worker and you'd have done the same if she were a man.

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I'm not going to say that dating coworkers is categorically "wrong", but at a minimum it's highly risky behavior; there are lots of ways that this can cause serious problems. For example, I had a friend who got a job at the same company as his then-girlfriend in the same department; they eventually broke up, but their cubicles were still next to each other. Having to be in such close proximity to her every day was quite awkward for both of them. It also made it much more difficult to stick with their decision to break up (which was clearly the correct decision in that case, given that their relationship was becoming increasingly toxic by that point).

Another related potential problem with this arrangement is that work issues can frequently become relationship issues and vice versa, so it complicates both your romantic relationship and your working relationship.

There's also a serious risk that it could be interpreted the wrong way, even if you're otherwise respected at your company and in the field. (See Bill Gates by way of example).

Also:

...I'd prefer not to be "just friends" either as I don't tend to be friends with woman that I'm attracted to.

This point is potentially controversial (so do with it what you will), but many people think that your coworkers should not be your friends, and that doing so intrinsically compromises professional boundaries. Again, not everyone is of that opinion, but you may want to consider whether you agree with view that or not.

In general, I would encourage you to think through what kinds of boundaries you want to have between your professional life and your personal life before you go ahead with asking your coworker out.

Also, please do be sure to check company policy on this matter as some companies forbid it outright (or, at least, forbid it for people that are "directly" working together, and certainly for cases where one person is in a supervisory role over the other; you don't indicate whether that's the case for you, but either way you should check company policy on what is and isn't allowed).

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You've correctly identified that it could be a problem if you ask her out before the conference, and she's then "trapped" with you, without a way to escape the situation. Unfortunately some guys don't take no for an answer, which makes things socially problematic for everyone (due to the very reasonable behaviour of those on the receiving end of creepy advances).

3 weeks might not be long enough for her to be comfortable being alone with you if she's not interested; you don't know whether she's had bad experiences in the past.

I'm pretty clueless myself, but one excellent piece of advice I came across is never hit on someone when they're in a situation they can't leave. (I seem to remember Taliesin Jaffe saying this, but I can't find it again now.) Most especially a waiter or barista who's stuck behind the counter and being paid to be friendly to customers (where the "can't leave" includes short term inability to walk away from a conversation) but the principle generalizes to long term them having to interact with you in future because it's their job to be there. That part is also true for a co-worker, depending on how closely you work together.

(And if you search for advice on how to ask out a barista, some of the advice might be relevant. Such as ask a mutual friend if she's single instead of asking her directly if she wants to go out might or might not be good advice. If it's a mutual friend that will tell her you asked.)

If you work closely together (separate from going to this conference), you need to account for the possibility that she'll be uncomfortable if she's not interested, if she doesn't have a way to keep her distance for at least some time. If that's the case, as other answers suggest, be sure to move slowly, don't just ask her out of the blue if she wants to go out on a date.

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So I've recently started a job and

Full stop right there.

While I very strongly advise against any workplace relationships, being a recent hire makes this 1000x more so. You don't fully know the culture or HR's tolerance for this, PLUS you're likely under watch for just this kind of situation.

"Don't fish off the company pier" applies especially here.

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When should I ask my female co-worker out?

I'm going to agree with sf02, with a different explanation.

P.S. I do not care about the outcome, if I get rejected I'll just tell her that'll it'll not compromise our working relationship, but that I'd prefer not to be "just friends" either as I don't tend to be friends with woman that I'm attracted to.

That you said this shows that you're not thinking of your co-worker as a human being with her own thoughts and opinions and desires. It seems to be all about what you think and what you want.

Look at this situation from her point of view.

If you ask her out, and get rejected, either--the most likely case--she's merely uninterested because she's not even thinking about you in that way at all because you're just another new guy and she doesn't even know you, or--worst case--she's noticed you and she's anti-you for some reason. Either way, you have just deteriorated her work environment.

She's probably already had n other guys at the company ask her out, you're number n+1, and she's going to spend the rest of her time there wondering whether every new guy is going to try to ask her out. Plus she's going to have to worry whether you're going to be one of those persistent guys that can't take no for an answer.

For the next days or weeks after you ask her out and get rejected, she's going to be looking over her shoulder to see whether you're coming, and going out of her way to avoid you, which may mean missing out on gatherings and activities that she enjoys so she doesn't accidentally run into you and give you ideas.

Just don't, for her sake, not because you don't want to cause trouble with HR. If you actually cared about her, you'd think about the possible effects your advances could have on her.

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  • Now I don't know about you but I in the past I have been friends with people that I have found attractive and all I can say is that it hurts. You see them as a potential partner whilst they only see you as a friend. Not really a good combination for a friendship either. Maybe I worded myself wrong, maybe instead of saying "I'd prefer not to be just friends", instead I should say "I would like to keep this relationship strictly professional". P.S. By friends I mean hanging out outside of the workplace as friends, not as in being friendly in the workplace. Commented Aug 27, 2022 at 9:01
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... if I get rejected I'll just tell her that'll it'll not compromise our working relationship, but that I'd prefer not to be "just friends" either as I don't tend to be friends with woman that I'm attracted to.

WOW. What you are basically saying is that you only care about her looks. I'm guessing that you don't really have any chemistry with her, you just find her attractive and want to get busy. 'Asking her out' at this point is probably a bad idea. This is the absolute wrong mindset if you are looking for a relationship. Besides, openly declaring you are attracted to her and don't want to be friends is heading towards creating a hostile work environment. You should at least be 'friendly' with your coworkers.

Take it slow. Talk to her. The business trip where you are traveling with her would be a great time for this. After the trip, try to get her to go out for group activities where there's zero pressure. Find out her likes and dislikes. Let's say you share a taste in music. Go out on a date with someone else and talk to her about it. If the date goes well, great! If the date doesn't go well you might be able to tell her something (truthful) like "It wasn't great. She didn't even know who [a shared band we like] is. Oh, well. There's plenty of other fish in the sea..." Now she's thinking about you going out with other women so you seem more desirable, and she knows she meets at least some of your criteria for a partner. If you're at all attractive to her she will be thinking about how you two would be as a couple and wondering why you don't ask her out. You'll be set when after one of those group activities you two are having such a good time that you are the only ones left after everyone else goes home.

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    This makes a good point (although other answers are better) - if you're not interested in friendship in a relationship, you're not interested in a lasting relationship at all. So the OP just wants sex - it's just about him. It would be better for her if he didn't waste her time. I doubt he cares what's better for her. Commented Aug 24, 2022 at 16:04
  • Let's not kid ourselves, initial attraction is always born out out of physical attraction and then is built by emotional attraction. The whole point of the date is to realise whether you have this emotional attraction. Now I don't know about you but I in the past I have been friends with people that I have found attractive and all I can say is that it hurts. You see them as a potential partner whilst they only see you as a friend. Not really a good combination for a friendship either. Maybe I worded myself wrong, maybe I should say we should keep this relationship strictly professional instead Commented Aug 27, 2022 at 8:41
  • It doesn't have to be about sex at all. Just being interested in someone romantically, and they don't reciprocate, is clearly emotionally painful for that person. I completely understand why OP would prefer to not be friends at all rather than deal with that.
    – rjh
    Commented Aug 28, 2022 at 9:32
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When should I ask my female co-worker out?

Never.

The workplace is not a bar or club where such behavior is acceptable or encouraged. Asking out a coworker is at best unprofessional, at worst harassment and could cost you your job. If you value your job, you should forget about dating coworkers.

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    Literally this. Don't use work as a dating pool ever. Commented Aug 23, 2022 at 20:59
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    "Coworkers can't date" seems to be an American thing; when Walmart tried to expand to Germany and implemented the same policy, unions sued and easily won at court. And the workplace has the advantage you can actually chat and learn about each other before making any move that hints at dating. The important message is not "don't ask a coworker out", it's "If the coworker isn't interested, don't let that affect your professional relationship". Commented Aug 24, 2022 at 6:39
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    Sorry, but millions of married couples would strongly disagree with this answer. Over 20% or all married couples met at work. monster.com/career-advice/article/love-at-work. Dating at work can be done well and it's a major connection point
    – Hilmar
    Commented Aug 24, 2022 at 7:10
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    @GuntramBlohm: it's perfectly normal and accepted to date at work in the US as evidenced by the fact that 20% of US married couples have met at work
    – Hilmar
    Commented Aug 24, 2022 at 7:11
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    @GuntramBlohm when the OP is worried about being "friend zoned" and says he will explicitly tell the coworker that they will not be friends if rejected, clearly they lack the maturity to prevent this from affecting their professional relationship.
    – sf02
    Commented Aug 24, 2022 at 10:40
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One thing I would add to existing answers is that you should pick a time when you really don't expect to be working alone together, or spending a lot of time together in a small group. Just before the trip would clearly be a particularly bad time, but consider other situations as well.

At best it would be awkward to be forced to spend much time together, but it could be much worse if it goes particularly badly . Either or both of you could end up being very worried about the effects on your career. Don't forget she may have been found attractive by less thoughtful people in the past, and ended up having a hard time of it.

Instead, reckon on a time when you'll be able to demonstrate gradually that your subsequent behaviour will be somewhere between politely professional and respectfully friendly depending on how she behaves.

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My suggestion is that just be a bit more patient. Wait for some time, maybe one month minimum. Till then revisit your thoughts, observe her closely, and then you will be able to easily grasp whether the feeling is mutual or uni-directional. Thanks!

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    I fail to see what this adds to the top voted answer that was posted several hours before
    – gnat
    Commented Aug 24, 2022 at 11:52
  • I just mentioned what I thought is correct. I have no concern with any of the answers.
    – GMD
    Commented Aug 24, 2022 at 11:59
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    What makes you think people can "easily" grasp whether the feeling is mutual? If you have an easy way to see, you should probably put it in your answer. Most people find it quite difficult to figure that out.
    – Erik
    Commented Aug 24, 2022 at 13:22
  • It is a feeling and everybody has a different experience. For example, she will try to long the conversation, she will remember what you like or dislike and on and on. Secondly, yeah, sure I'll try to answer in depth in the future.
    – GMD
    Commented Aug 24, 2022 at 13:29
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Don't ask her before this trip thing. And don't be sizing her up during the trip, however handy the work is. It's a pity there no one else on that trip to keep you honest. You have some reflection to do before making your next move.

Wilfully mixing work and personal relationships is really foolish. The operation of a good workplace hangs or falls on a basic human (physical/mental/emotional/moral) trust between people of all ages, sexes, marital statuses, creeds, races and capabilities. Cultivating this "trust environment" and guarding against all dangers to it is primarily the role of HR and management. But all employees really have an interest in maintaining it: a stable workplace is best for everyone. Indeed the workplace - rather than home, school or college - is where most of us first learn how to relate fairly and purposefully with other people. It shows us when to offer assistance to others and in what manner to do so. This seems boring as a mound of earth when we are first compelled to do it. Yet it is something that stands us in good stead when dealing with strangers in the world around us, at bus-stops, train stations, airplanes, hotels, walking down the street, on vacation, etc. And of these humble encounters many loves are born.

All that said, we live today in a world where I guess > 80% of women work outside the home through choice or necessity. This leads to more social mixing and more sober and no-nonsense engagements between men and women of the same age during the day. It may happen that two people with an irresistible attraction will meet. Unlike commenter Erik, I have never had any problem in (most palpably) knowing when an attraction was mutual. But maybe that is just a reflection on how people like me see these things and not a general human faculty.

Whatever you do, you have to recognize that if this attraction between you and the other party becomes a "works relationship" then, at work, it will not simply be something that concerns you two alone. Other people will feel that challenging either of you - even on fair grounds - risks falling out with the other. Some colleagues may see it as an ambitious move on your part and/or a threat to their own. I doubt if HR will be keen on it as it would set a precedent for other works relationships and all the complications thereof.

It seems to me that if you both look into each other's eyes and see a reflected love then it's going to be so much easier for you to have this forever if one of you gets a job elsewhere.

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