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I have developed strong liking towards my co-worker for the past week since I met her and I cannot stop thinking about her. Although we only chat about work during work I want to ask her on a date. But at the same time I do not want her to feel awkward after that and spoil the current relationship which can hamper the work. How do I approach her without making her feel awkward or should I just ignore the feelings and concentrate on work? We both are working as an analyst at a fintech firm. This is also our first job out of college.

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    Are you sure company is ok with it? Some companies may have rules against these kind of relations. Also, if you chat strictly about work only, this might not be best idea. – Ege Bayrak Jan 31 at 13:26
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    After dealing with the matter of company policy, the rest of this question will just be interpersonal skills, for which there is a Stack Exchange site that has dealt with this in many different questions. – Luke Sawczak Jan 31 at 13:31
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    @LukeSawczak Just because a Q is on-topic on another site doesn't mean it shouldn't be here :) This situation is common enough that we would benefit from keeping it – rath Jan 31 at 13:39
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    I would argue strongly that this question should remain on Workplace. Asking out a coworker is very different from asking out people you know through other channels and must be done within the context of the workplace environment and relationships. – dwizum Jan 31 at 13:53
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    What if you succeed, end very badly, and then you still have to work together every day? – Thorbjørn Ravn Andersen Jan 31 at 14:46
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Don't do it unless you are willing to risk your career.

A lot of answers are saying to check if your employer has a "no fraternization" policy. However, lack of policy doesn't really protect you. Even if your employer does not have a specific policy against it, if your request to go out on a date is unwelcome, it can still be considered harassment...and once you ask her, there is no way to undo it if it doesn't go well.

  • I don't think anyone mentioning relationship policies has any intent to imply that the existence or lack of such a policy would offer any sort of protection. The policies are being mentioned purely because it's something you should know about, if it exists, and you're potentially about to enter a relationship. At any rate, this doesn't really answering the literal question being asked. – dwizum Jan 31 at 20:40
  • @dwizum My point is that you shouldn't do it whether there is a policy or not. If a policy exists saying you can't fraternize then you shouldn't. If no such policy exists, then you still shouldn't. If the employee asks her out anyway, they are risking their career no matter what the policy says. So knowledge of the policy does almost nothing for the employee. – David Cram Jan 31 at 21:31
  • Okay, thanks for the clarification. Although, I think my last sentence still applies - the OP didn't ask if he should do this, he asked how to do it. If you'd like to frame challenge you could provide some more backing or explanation as to your position. Or maybe you can expand on your answer in a way that does actually address the "how" question. Editing in either of those ways may help your answer to be more helpful and attract a more positive score. – dwizum Jan 31 at 23:42
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    @dwizum The OP did ask if he should do this: "or should I just ignore the feelings and concentrate on work?" – Jon Bentley Feb 1 at 0:41
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IMHO, you shouldn't.

I had this experience before, and I was successful in asking her out and we started dating, BUT, after a few weeks or months, if something bad happens out of your workplace e.g. a bad discussion about your relationship it is VERY hard to keep everything straight at work. I.e it is very hard to separate personal life and work life, even if you both are very mature, some weird behaviors leak here and there. You both just got out of college, so I assume you may not have enough experience to be able to emotionally handle all situations.

In my case, we broke up after 4 months, and we kept working at the same office, later she left the company because when we broke up, it was very hard for her.

And as other mentioned, some companies policies do not allow dating and even if they do, this situation might not go well on you socially speaking (like it did not go for me).

Now... if you really wanna go for it:

I would recommend you start small personal conversations during work (on appropriate environments and schedules of course). When you stop talking because you need to head back to work and you feel both of you wanted to keep talking - you feel incomplete, then you have a good sign that you both would like to continue this conversation later on.

From here on, I would continue talking during work until I find an opportunity to say something like:

Hey, this restaurant nearby just opened, do you want to check it out?

Asking her out during work lunch is a good idea even if other colleagues come in together, because you all will have the opportunity to talk about other things that are not related to work, and you may have the opportunity to know more about her and vice-versa. These small steps may lead you into a more personal, 1-to-1 lunches, dinners, etc...

  • You may want to add to the story who ended it and why, as she was the one who had to leave. – Thorbjørn Ravn Andersen Jan 31 at 14:46
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    @ThorbjørnRavnAndersen it doesn't sound like she had to leave, just that she chose to because working with an ex was uncomfortable. That can be true regardless of who ended it or why. – Kat Jan 31 at 22:29
  • @Kat I did not mean that the employer forced her to leave, but that she chose to of her own free will. Most likely because she felt uncomfortable, and I think that the story why is very relevant here. – Thorbjørn Ravn Andersen Feb 1 at 2:28
  • @ThorbjørnRavnAndersen she chose to leave because she became more emotional with our relationship than I did, so when I decided to break up with her, she could not handle very well (at the time I was 23, she was 22). A few weeks on, working together was being very harsh on her, so she decided to leave the company. I had bad social problems as I mentioned because everyone thought I was the reason she was crying at the bathroom, and indeed I was. People started thinking I was a bad boyfriend, and even the CEO came to me to understand the situation. – renanAlmeida828 Feb 3 at 13:19
  • @renanAlmeida828 So she fell in love with you, and you didn't so you broke up, and then she had to work with you every day? I probably would have left too if I were her. – Thorbjørn Ravn Andersen Feb 3 at 13:24
23

Lots of people date coworkers. You spend a significant portion of your life at work and may naturally develop feelings for people you meet there. It can be natural to try to pursue these feelings, but the workplace is a pretty special context for meeting a significant other and that context needs to be kept in mind at all steps and phases of the relationship.

Your question was,

How do I ask co-worker out on a date?

While this question is directly answerable, it makes sense to consider the bigger picture of workplace romance. Namely, consider the following:

  • Does your company have a policy about relationships? Many employers require them to be disclosed, at least, and there are sometimes very specific limits based on position or role (i.e. a supervisor may not date a subordinate, or two people on the same team may not date).
  • Are you ready for this to not work out? Are you ready to keep working with this person if they say no? Or if you date for a year and then have a messy breakup? The fact that you've said you can't stop thinking about them may in fact mean that you have genuine feelings about this person, but that may also mean it will be very difficult for you to handle a rejection. You need to be ready to let this person go before you take the step of initiating a relationship.
  • Do you have an "exit plan" based on that point? Before you even think about how to ask, consider how to handle no, while maintaining a professional environment.
  • It's hard to give advice about feelings, but the difficult part right now is that you only know your own feelings. You don't know how your coworker will respond, or how they will handle rejection or future relationship issues. Even if you think you are mature enough to handle a "no" or a future breakup, you're taking a gamble on the other party having the same capability. Since you are the one initiating, you need to make sure your "exit plan" includes your coworker being very upset by this, to the point that they can no longer work with you. In other words, it's not fair to initiate a relationship and then expect the other party to handle things in a way that you'd be compatible with.

Also, it's worth considering that once a relationship has started, you will still be coworkers, and you will need to be able to handle that role without interruption or issue. You will also need to handle the fact that the workplace rumor mill loves to talk about workplace romances. If you two date, you need a plan for handling rumors and discussions about your relationship. If your relationship makes it past infancy, be ready to consider the following, and discuss these points with your new significant other:

  • Have guidelines about how you two interact with each other at work. Make it clear between the two of you that you are employees first while you are in the office. You must still be able to get your jobs done and be productive. Sometimes, this means having strict rules: maybe you two can agree to not talk about relationship matters while on the clock. Make sure you can focus first on getting your job done.
  • Have guidelines for how you act in front of coworkers. Some people are uncomfortable showing affection in any way in front of coworkers. You don't want to try try to hold hands as you walk across the parking lot on your way in to work if your significant other would be uncomfortable with that. Talking about this ahead of time clears the air and sets expectations so you won't feel rejected when they pull back from your attempt at holding hands.
  • Have guidelines for what you share with coworkers or how you talk about your relationship with them. Some people are friends with lots of people at work and will naturally want to talk about things like the amazing date they went on last weekend. Other people will feel really uncomfortable if their significant other is telling others at work about their dates. Again, clear the air upfront and set expectations.

Those things out of the way, we can get back to your actual question: How do you ask out a co-worker?

Ultimately, your approach needs to be within the above framework. It's probably a good idea to begin with some work-centric interactions, or at least work-related interactions. If you have a cafe in the office for lunch or breaks, ask if you can sit with them and make small talk. It should be clear if there are feelings of interest, although you need to make sure you're not just getting excited and misinterpreting a friendly coworker for someone who is interested in you. If you feel that these casual interactions are going well, you can follow the natural progression and ask something like,

Hey, I'm having fun chatting with you, would you like to get together outside work some time? Maybe we can grab coffee or hang out this weekend.

The wording is subtle but important. While it's fine to start with work-centric interactions as a way to test the waters, when you decide to actually ask the other person out on a date, you need to make sure they understand you're asking them out on a date, and not just trying to continue workplace conversation or work-centric interactions after hours, or be "friends" if what you're after is a more romantic relationship.

The timing of when you ask can also be important - ideally, you'd ask when there isn't a strong work focus required (i.e. don't ask at the beginning of the morning standup, or during a project meeting). Asking while on a break, or at the end of the day, is appropriate because it's less likely to distract from work topics or cause a scene.

Once you've asked the question, you need to respond appropriately to the answer. In fact, it's arguable that your plan for responding to their answer is probably more important than the actual words you use to ask them out. This is especially important within the workplace context and ties back in to the first bullet list above. If the other person says no, you need to be ready to consider the following:

  • Continue having professional and productive work interactions with them every day. Instantly trying to avoid them as much as possible will just make things awkward for everyone. If you can't bear to be around this person, much less keep working together after a "no," then don't ask.
  • DO NOT bug them, pester them, or try to change their mind. Don't suddenly be extra nice as a way to win them over. Don't show them preference in work activities. No means no.
  • Respect their privacy. Don't talk to other coworkers about how this person rejected you. Don't badmouth this person or treat them any differently. Don't give the rumor mill any fodder.
5

You've only known her for a week and you've only talked about work issues, and you want to ask her on a date even though you know pretty much nothing about her. From a female perspective, it sounds like you're objectifying her a bit. I would be very uncomfortable if a male coworker under those circumstances asked me out. Women have historically struggled with being taken seriously in the workplace, and this situation would bring up several questions for me. Does this guy respect what I bring to the table as a coworker, or am I only a romantic interest to him? Is he agreeing with me because he really thinks my ideas are good, or is it because he's trying to curry favor with me?

Or worse: is he some kind of creepy stalker who's obsessed with me? I once worked in an office where we had one of those, although was fortunate in that it wasn't me he was obsessed with. She finally wound up taking a restraining order out on him after he was fired for his behavior and persisted in trying to contact her afterward.

How do you know she doesn't already have a boyfriend or a girlfriend? She might not wear a ring, but that doesn't mean that she's not already in a serious relationship. How do you know that there's not an immediate deal-breaker (religion, politics, etc.) on either side? This is not like high school where you can get your buddy to ask his sister if she knows anything. Trust me, you do not want to get the office rumor mill cranked up. She will not appreciate finding out about it through the grapevine and it runs the serious risk of torpedoing any kind of relationship, workplace or otherwise.

Get the thought of dating her out of your head for the time being and give her the respect of getting to know her as her own person first, instead of just obsessing over her as a possible object of your affection.

  • Funny you said "curry a favour" given the OP's Country of origin. Although I completely agree, given it's only been a week of them knowing each other, I would personally take it slow. – Monstar Jan 31 at 23:03
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May I ask you a bold and improper question?

If she says yes, you may ask: “Would like to meet outside work, in a personal capacity?

If either question is answered in the negative — it happens — reply with something like “Very well, I hear the answer and I will not ask again.” This has two purposes. First, it is an acceptance that the relationship is professional and can comfortably stay professional. Second, it says that if she should change her mind — it happens — it is for her to take some action, not you.

Good luck.

But know that disappointment is likely, even though not certain.

4

I will start by saying it's ill advised to do so, but, if you must....

First make sure it's okay with the company, many have "no fraternization" clauses in the employee handbook, check that first.

You may want to casually ask HR about it, but keep in mind HR IS NOT YOUR FRIEND

Then, any approach you make to your coworker should be outside of company hours, perhaps as you are both leaving. You do not want to create any awkward situation during company hours, should anything go wrong.

If your coworker says no, do not bring it up again.

2

How? Very, very carefully.

The big problem is that you have a very strong liking for her, but she doesn't have a strong liking for you. She barely knows you. In that situation, trying to ask her out on a date can badly misfire. From her instantly disliking you to reporting you to HR for harrassment, anything is possible if you are unlucky. I would spend some time being a good colleague first so that she knows you and appreciates you as a colleague; that reduces your risk significantly and improves your chances for success. Also by that time you should know her much better and not think of her constantly and you may figure out this is all a bad idea.

If you are rejected - which is the most likely case - one thing you must not do under any circumstances is to hold that against her and treat her badly for it. That's what a low life would do. (And the fear of this happening is what makes the situation uncomfortable for woman).

Next consider what happens if you actually manage to take her out, you get together, and after some time you split up more or less amicably. Perhaps less. That would be no problem if you are both adults acting adult. Many people are not. So this would be a significant risk for you (and for her). Worst case you will have to leave your job about it. Be aware of that.

Now the best case is you find the love of your life... Your company might not like it. It may have consequences for one of you. Prepare for that. If she's the love of your life you shouldn't have a problem finding a new job if needed.

1

Let's get you a few simple steps forwards.

  1. Suggest a group outing, plan it, and ensure a safe environment for both yourself and the person in question. Don't just include the person in question. A group outing to a restaurant/bar after work or on a weekend is a good start. This does an important step of setting up a neutral ground where you can speak with the person 1-1 outside of the context of work.
  2. If the person is receptive to such outings, increase the frequency. Again, make sure to ensure everyone is included. By only focusing on the person, you remove that safe place.
  3. Be sure to speak more with the person during such outings, but don't single them out. Talk to everyone evenly. If there is chemistry, it'll make itself apparent there.
  4. During one of such outings if they are going well, speak to them privately / away from the group if possible. Make it clear what your intentions are (ie: I'm interested in seeing you) but also maintain that safe space (ie: I don't want this to affect our work, I respect your decision)
  5. Set up and maintain clear boundaries regardless of the outcome. It's unprofessional to let personal feelings bleed into the workspace in most, if not all workplaces.

I think we've explored all the reasons to not do this, but let's be honest, we've all thought about this at some point. I've done this myself and it didn't go so well, but life keeps going. My co-worker asked out somebody else and it worked out well for him.

It all boils down to how well you're able to separate work and life.

Weigh your decision carefully here. If you really believe that this is an opportunity you cannot pass up, go ahead but tread lightly and be respectful.

When a person confesses their attraction to another, we hand them responsibilities that they (oftentimes) do not want. Do your part and maintain that level of professionalism in the workplace, and save all such discussions/talks to outings that are out of the workplace.

0

There are various reasons why it is advised not to build a personal romantic relationship with a colleague. If you really want to be in a relationship, the best idea would be either of you switching to a different organization and then be in a relationship. This is not required for you to start interacting with them, but this is going to be the need in the future should you both get along.

Are you onboard with the idea of switching jobs (assuming the fact that the other person would not be), if you two get along and proceed towards a relationship? If yes, then you can proceed with socializing them, otherwise, as you said, forget about this and concentrate about work.

Now, given that you understood and are OK with the path forward, you can start talking to her - the best place to start is to talk about common interests, maybe in the beginning it'll be the new business areas or new ventures related to the analysis you do, slowly moving in to the personal hobbies etc. Just like any other relationship, you need to invest (time and effort) into it.

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    You make some valid points, but you are not really answering the "how do I approach" part. – TheRealOha Jan 31 at 13:51
  • @TheRealOha Added a paragraph to address that part. – Sourav Ghosh Jan 31 at 14:43

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