How to Ask Out a Coworker With Confidence? Navigating Workplace Romance

This post contains affiliate links. If you click and buy we may make a commission, at no additional charge to you. Please see our disclosure policy for more details.

Sharing is Caring!

You joined this organization a few months back. Everything was going well in your office. You were happy with your professional relationship with your colleagues. Then this girl or guy joins your team. And since then, you have been crushing on them.

Is this your story? Have you developed a soft corner for one of your colleagues? Do you want to ask them out on a date?

Well, workplace romance has become common these days. And why won’t it be? You literally spend almost all your day in the office. And during that time, developing feelings for someone is natural.

But, you know, workplace romance can be tricky. You have to be very careful that you maintain the perfect balance between personal and professional relationships.

Also, you need to ensure you don’t embarrass yourself in front of your colleagues. If your coworker you are crushing on doesn’t accept your proposal for a date, you have to handle the situation cleverly while maintaining your self-worth.

Now, you may ask, “How to ask out coworker” properly so that the chances of getting rejected are slim?

That is what I’m going to discuss here. But before I begin, remember one thing, while most offices are okay with workplace dating, there are some that have an anti-dating policy in place.

So, it would be great if you could have a look at your employee handbook once. Also, you can ask your HR if there is any policy regarding workplace dating.

How to Ask Out Coworker for a Date?

Now that you know there is no rule against dating in your workplace, it’s time that you look for ways you can ask your office crush out on a date.

Here I have come up with some tips to help you out. Also, I have included some do’s and don’ts so you don’t make fun of yourself in front of your colleagues.

Excited already, huh? Let’s get started, then.

1. Confirm That Your Coworker is Single

Confirm That Your Coworker is Single

This is the first thing that you should be sure about before planning to ask your coworker out. Know if they are already seeing someone, as this will save you two a lot of embarrassment and, of course, time.

How close are you with your coworker? Are you friends with each other on social media?

If so, then you can check there. Social media platform such as Facebook lets you add your relationship status.

Also, you can check their recently-uploaded pictures and see if there are pictures of their potential girlfriend or boyfriend.

If there is someone in your workplace who is close to your crush, you can take their help and ask them to find out if they are seeing someone.

And if nothing above works, you can ask your coworker directly. You can say something like, “So, what are doing this weekend? Do you have plans with your girlfriend/boyfriend?”

And you will know for sure if they are single.

2. Feel and Dress Your Best

If you are now sure that your coworker is single, it’s time for you to prepare yourself to ask them out.

Wear your most beautiful dress. Of course, make sure that it is appropriate for wearing at your workplace.

Shower and spray a heavenly-smelling perfume. To look your best, you can go for a haircut a few days before you plan to ask them out. This will give you that freshly-groomed vibe.

When you look good and smell good, it boosts your confidence level. And you may get “yes” as an answer. Who knows?

3. Rehearse in Advance

Rehearse in Advance

When it comes to dates, planning in advance is always better. Of course, that doesn’t mean that impromptu dates are not fun. I like unplanned dates.

But since we are discussing workplace romance here, it would be better if you plan everything so that you can skip the embarrassment and awkwardness.

Planning becomes easier when you know their likes, dislikes, and hobbies. Make it seem casual, so if they are not interested, they don’t make a scene out of it.

If your coworker likes watching Marvel movies, you can start by saying, “You know, I have been waiting to watch this Marvel movie since its trailer was released. And it is releasing this weekend. Do you want to join me?”

No matter what you say, always plan and rehearse in advance so that you don’t miss your chance or make it look awkward.

4. Ask Them Out at Someplace Quiet

You don’t want to create a scene at your workplace, do you?

And for that, the safest bet is to ask your coworker out where there are very few to no people at all.

If you ask them out when they are surrounded by other colleagues, they may say “no” as an answer, stressing what others would think. Also, hearing “no” in front of all these people can be a bit embarrassing for you.

Also, don’t ask them out when they are busy working on some priority project, as the chances are that they will not hear you with full attention and might reject your proposal.

This is your only chance, and you don’t want to blow it, right?

You can ask them to meet you at the cafeteria when it’s almost empty. And if nothing works, you can ask them out with a text.

5. Don’t Ask Your Subordinate or Boss Out

Don’t Ask Your Subordinate or Boss Out

If you are a K-drama fan like me, you might have watched tons of them in which the boss falls in love with their employee, and they end up being together happily.

But your life is not a K-drama. No matter how much the idea of workplace romance seems exciting, it could be very tricky in real life. There are a lot of things you need to take care of, and one of them is having a balance between personal and professional life.

Do you find your boss attractive? Do you think it would be great if you could date them?

Keep your thoughts to yourself. It’s better not to approach them, as it can have a negative effect on your career. Also, the chances are that your colleagues will avoid you because they may think that whatever they say to you, you will rat them out to the boss.

Dating your subordinate is even trickier. They might be forced to accept your offer as you are the employer. You should not, in any way, cross the line between an employee and an employer. This can even ruin your business and reputation.

6. Just be Your Real Self

You spend a lot of time in your office, which means you spend a lot of time in the surrounding of your coworker whom you are crushing on.

It can be that you don’t talk to each other. But they are completely aware of you being there. Maybe they also check you out.

So the best you can do is be yourself. Don’t fake it, as they may catch you being unreal.

If you are feeling anxious, that’s okay. It’s pretty normal for people to be a bit tense when it comes to asking someone out. Also, your coworker might experience the same if they also feel the same way about you.

7. Be Casual

Be Casual

You don’t want this entire “asking out” thing to be a scene in your workplace, right?

And for that, what you can do best is to keep it casual and not too noticeable.

If they like coffee, you can ask them casually, “I’m going to have a cup of coffee at the newly-opened café opposite our office building. Would you like to accompany me?”

Coffee dates are great as first dates. And the chances of getting rejected in this case are little, especially if they like you too.

Also, if they feel awkward to meet you outside the office, you can ask one or two of your other colleagues to join.

8. Don’t Rush Things

Know what you are getting into while asking your coworker out. If they are interested in you, talk to each other and think of a way to keep a balance between your work life and your personal life.

You know, your workplace romance can fail at any time if you rush things.

If your coworker hasn’t answered you yet, don’t ask them again. Give them some time to process what you have asked. They should think about the pros and cons that come with dating their colleagues.

And if they agree and you start dating, don’t rush things. Think before you start taking things to the south.

9. Don’t Let Your Feelings Hamper Your Work

Don’t Let Your Feelings Hamper Your Work

When you develop feelings for someone, they are always in your mind. And as we are talking about office romance here, they are always around you.

Seeing the person you like looking at you or crossing you can give you goosebumps. But that doesn’t mean you will let your feelings play with your work caliber.

When you are at a meeting, flirting with each other in front of colleagues can hamper your reputation and risk your career.


Human feelings are complicated. We don’t know how and when we fall for someone or what makes us attracted to someone.

And so, I don’t blame you if you have grown feelings for your coworker and want to know “how to ask out coworker?”

Try the tips I have shared here. And don’t forget to tell me if they agree to go out with you!

Sharing is Caring!

Leave a Comment