5 non-awkward steps to ask a coworker out

Updated on August 9, 2023
how to ask a coworker out

If you are wondering how to ask a coworker out on a date, you might be imagining all sorts of scenarios of how to do it and what will happen after you essentially communicated that you have romantic feelings about the person.

This can turn into a major source of anxiety and frustration in your day-to-day life if you don't take any action.

For example, what if you ask your workplace crush out through a romantic gesture, but they say no? Things will surely get a little awkward after that, right?

Well, this doesn't have to be the case. Here you will find a step-by-step guide on how to ask a coworker out without making it awkward that actually increases your chances of getting a positive response.

Is it appropriate to ask a coworker out?

It is appropriate to ask a coworker out on a date as long as you can take a rejection and your professional relationship won't be affected after that. You also need to consider what your company policy says about employees dating. Some employers have a strict no-dating policy.

It would be great if your coworker responds to your feelings and agrees to a date. According to this survey by SHRM, workplace romance in the USA has been on the rise in recent years, with 33% of the participants saying that they are currently dating a coworker (or have dated in the past).

But you have to be prepared for rejection in case your coworker says no. If that happens, your ego might be a bit bruised, but it would be in your best interest to remain professional.

Don't let your emotions get in the way. If you continue to bother your coworker, they might find your behavior to be quite toxic.

Survey on asking a coworker out

We asked over 200 professionals if they would ask a coworker out on a date despite knowing that if they are rejected, they might end up in an awkward situation. Here is what we found out.

poll about should you date a coworker

A total of 224 professionals took part in our survey. The majority said that they wouldn’t ask a coworker out and risk awkwardness.

  • 87%% said no.
  • 13% said yes.

Is it OK to date someone you work with?

It is okay to date someone that you work with as long as your relationship does not violate company policy. Another thing to consider is that romance in the workplace can get in the way of professional duties. A failed romantic relationship between coworkers can have numerous negative implications.

Attraction between coworkers is perfectly normal and somewhat expected. People who work together and face the same daily challenges have a lot of shared social context between them.

This can turn into the basis of a beautiful life-long romantic relationship.

The main concerns of employers when it comes to employees dating is conflict of interest, sexual harassment at work, defamation, and eventual legal consequences.

That is why some resort to strict no dating between coworkers policy.

If your employer finds out that you are dating a coworker, one or both of you might be asked to resign in case the relationship violates company policy.

On the other hand, some employers may be fine with their workers dating. However, they might require a love contract to be signed.

How to ask a coworker out casually in 5 non-awkward steps

How to ask a coworker out casually in 5 non-awkward steps

If you tell your friends that you have a crush on one of your coworkers, they might tell you to “just be yourself” and “just ask them out” – this is probably the worst possible advice that you can get.

If you follow it, you will totally make the situation awkward, which is exactly the opposite of what you are trying to achieve.

Instead, here is a more logical, less awkward 5-step approach that actually increases your chances of becoming close to the person that you are interested in.

1. Check their social media profiles

You might feel a little dirty about doing this, but it is a necessary evil. Go to Facebook, type in your coworker's name in the search bar, and find their profile.

Go to the About section of their profile and check their relationship status.

If the person is in a relationship, it would be very unwise of you to ask them out on a date.

If their relationship is not specified, then move on to their most recent photos in case they are accessible. Check if your crush has multiple pictures with the same person.

Are they holding hands? Are they hugging and kissing? Do they appear like a couple? It's probably because they are.

But if their profile specifically says “Single” and the photo check does not reveal any red flags, then you can move on to the next step.

2. Become workplace “friends”

In case you are not particularly close to your coworker, then it would be better if you get to know them a little bit. To achieve this, use every possible opportunity to socialize with them at work.

For example, in case they are a new employee, it would be perfectly appropriate to introduce yourself whenever you get the chance and shake hands. Here is what else you can do from then on.

  • Greet them whenever you see them and smile
  • Talk to them by the water cooler about work and the weather
  • Sit next to them in the lunch area and chat casually about stuff
  • Make small talk in the elevator instead of just being awkwardly silent
  • Walk with them on the way to a meeting room and chat about work

Use these brief moments to build rapport by talking about work but make sure to slide in appropriate personal questions from time to time. Here are some examples:

  • Where did you grow up?
  • Do you have any siblings?
  • Where did you go to college?
  • What kind of music do you like?
  • What are your hobbies and interests?

The point is, to ask genuine questions that you are curious about. After all, you'd like to get to know the person a little bit before you make the decision to ask them out.

The purpose of socializing at work with the person you are interested in is to build rapport and a basis for the eventual date invitation.

This may take 2 to 3 weeks, depending on how often you are able to socialize with your coworker.

3. Follow them on social media

After a week or two of socializing and building rapport with your workplace crush, it would be perfectly fine to send them a friend request on Facebook or follow them on Instagram, where you can text them directly outside of work.

The next step is to slide into their DMs which is easier than you think it is. Simply comment on their story or start a conversation with a genuine personal question.

Hopefully, they will be happy to respond, and this can turn into a meaningful online conversation that furthers your relationship.

4. Probe carefully and gauge their reactions

At this point, you have a workplace dialog going on, and you can text them at any time. It is time to start probing.

If you have previous dating experience, then you will be able to gauge how your crush is reacting to all this attention they are receiving from you.

If they seem cold and distant, barely reacting to you when you engage them (probably out of politeness), then you can take that as a hint that they are not interested in you.

To avoid any awkwardness, it would be best to take a step back and not ask them out just yet. Simply be there for them, and focus on being good friends.

However, if they are responsive and pleased when interacting with you, then they might be giving you subtle signals to keep doing what you are doing.

Here are some signs that your coworker might be interested in you as well.

  • They ask you personal questions
  • You engage in long, meaningful conversations
  • They text you at random hours of the day
  • They like your social media stories and pictures
  • They ask you about your plans for the weekend
  • They seem to be open to the idea of hanging out

Still, even after all of this positive feedback that you are getting, your workplace crush might see you as just a good coworker and a friend.

However, if they have experience in dating, they might already have an idea that you are attracted to them but are probably waiting for you to ask them out. At this point, there is only one way to find out.

5. Ask them to hang out casually

The key to asking your coworker out on a date without making it awkward is to make it seem like it's not a big deal.

For example, you can text them that you will be going to an event this weekend, and they can tag along if they are free, you know? No big deal.

Instead of asking them out, simply give them the opportunity to join you in whatever you are doing to eliminate all the awkwardness.

It could be going to the gym, a walk in the park, or seeing an art exhibition. If they are interested in you, they wouldn't miss out on a chance to spend time with you outside of work.

If they are busy, they might say something like, “Hey, I am busy on Saturday, but I am free on Sunday.” This is a clear indication that they would be happy to meet you outside of work.

Simply make plans for the day when they are available.

If they give you an excuse for not being able to come without any specifics when they are available, then you can take that as a hint that they are currently not available for a date.

You might feel a little hurt after a rejection but stay consistent and don't let this affect your behavior towards your coworker. Remember that this is a person that you are genuinely interested in.

They might not be romantically available (at the moment), but you can still be good friends. Eventually, they might start to appreciate you a lot more and start seeing you as a potential partner.

How to ask a female coworker out

Ask a female coworker out on a date only after establishing some rapport at work. Give them the time to get to know you a little better.

This way, they will be more likely to go out on a date with you, or at least they will be more forgiving and sympathetic in case they turn you down.

And take “no” for an answer in case they tell you that they are not interested in you. Otherwise, they might file a formal complaint against you if you continue to bother them.

How to ask a male coworker out

If your male coworker is hesitant to ask you out, you can take things into your own hands. Ask them out casually if you feel like you have a great connection.

They will be happy to hang out with you outside of work. Asking them out might give them the needed confidence boost to take the lead.

And if you feel like the person is sending you mixed signals, check out the 33 subtle signs a male coworker likes you.

How to ask a coworker out over text

Texting is probably the best way to ask a coworker out because it minimizes awkwardness and provides psychological safety.

If you are not entirely certain that your crush is into you, then you can try a more casual approach. You can text them something like:

Hey, I'm going to [event/activity] this Saturday afternoon, wanna join?

Or, if you are feeling confident, then you can try a more direct approach. For example:

Hey, are you free this Saturday? Wanna hang out?

The best part about being confident and direct is that there is no room left for doubt. Your coworker will know for certain that you are interested in them.

Hopefully, they feel the same way about you. Also, they will respect you for being honest and direct rather than beating around the bush.

Having a massive crush on one of your coworkers can be quite stressful. Here are some useful tips on relaxing after work in case you are dealing with a lot of pressure lately.

How to get a coworker to ask you out

How to get a coworker to ask you out

If you would like to avoid taking the lead (and all the perceived associated awkwardness) by asking your coworker out, then there are certain things that you can do to make them ask you out instead.

The main idea is to show them in every way possible that you are romantically available and that you like them a lot. Here is what you can do to achieve that.

  1. Form a workplace friendship with the person you like.
  2. Change your relationship status to single on Facebook.
  3. Add the person as a friend and follow them on Instagram.
  4. Text them regularly and like their social media stories/photos.
  5. Engage in meaningful conversations about common interests.

Hopefully, your coworker will realize what all this attention means, and they will make a move. And in case the person you are interested in happens to be one of your superiors, then here are the signs that they might be attracted to you.

On another note, If you suspect that one of your coworkers has a crush on you and they are bothering you, then you can take a look at our guide on dealing with coworkers who annoy you.

Written by:
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galin office topics square
co-founder / office worker
Alex has been an office worker for more than 10 years. He is dedicated to helping other office workers to achieve the perfect life-work balance through well-being, effective communication, and building productive habits.

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