13 Respectful Ways To Ask A Coworker For A Date

Office Affairs | | , Copywriter & Content Writer
Updated On: December 28, 2023
how to ask a coworker out

Office romances may seem clichéd to some, but they are quite common. It is common to feel warmth for someone when you spend practically all of your time with them. So do you want to go on a date with your coworker? Are you wondering how to ask a colleague out? If they say yes, would it only be a passing fling?

From Jim and Pam to Amy and Jake we have seen office romances blossom on screen, but in reality, things may not always end well. It’s important to strike a balance between your personal and professional lives, especially when they run concurrently. According to research, Dillard and Witteman (1985) found almost 29% of respondents had had a romance in the workplace and 71% had either had a workplace romance themselves or had observed one. Many companies are amenable to office relationships. However, there may exist a few regulations, so make sure you read them before you start thinking about how to ask a colleague out. 

13 Respectful Ways To Ask A Coworker For A Date

It can be quite a task to ask a coworker out without making it awkward for both of you. Make sure your feelings and intentions are crystal clear before you make your move. The key is timing! You can’t just casually enter a room and ask someone out on a date without preparation or context. In the same way, you can’t randomly ask a coworker out over a text or in person. It will make things uncomfortable for you both. 

We promise this, though. It is not as tough as it seems. Here is your trustworthy guide to how to ask a colleague out.

Related Reading: 15 Signs Your Male Coworker Likes You

1. How to ask a coworker out? Wait for the right opportunity 

The first step is to ascertain whether they are single or not. This will help you avoid embarrassment. You can look them up on social media to see if they are dating someone. You can also approach a common friend who you can trust for assistance. Ask them if they are aware of the relationship status of the coworker you wish to ask out.

Start a casual conversation about this subject if you and this colleague are close enough. A good way to start a conversation is to find out what they are doing on the weekends and whether they have any plans with their partner. If they claim not to be seeing anyone, you can shoot your shot. However, if they say they are seeing someone, it is your cue to stop and move on.

2. Dress your best

If you are prepared to ask your coworker out on a date after learning that they are single, know what to wear – look your best. On your big day, it’s acceptable to take an additional 10 minutes in the shower. Wear your best cosmetics, best perfume, best hairstyle, best shoes, and make sure your attire is appropriate for the workplace. Also, groom yourself! You may make a favorable impression by doing this. Carry some mints or mouth fresheners before you approach them.

Be careful not to overdo it though. Your other colleagues may ask you what’s so different about today, and that is not something you want.

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3. Rehearse: Know what you are going to ask in advance

If you are certain that you want to go on a date with your colleague, make plans in advance. Don’t go and make an impromptu plan. It will be easier for you to plan something fun if you are aware of their interests, hobbies, and favorites. Make it as casual as you can. Impress them on your date, this may be your last chance.

You can ask them out to see a play if you know they enjoy theatre. It won’t be difficult to ask your coworker out on a date if you are well acquainted with them. For instance, our 26-year-old reader Aiden knew that his colleague, Betty, enjoys going for plays on her days off. He mentioned it casually during a conversation one day in the break room by stating, “Hey Betty, I’ve been wanting to watch a play for a while, and now it’s coming to our town this weekend. Do you wish to accompany me?”  

Also, before you ask your coworker out, rehearse. Write things down or make mental notes so that when it comes time to ask a coworker out without making it awkward, you don’t blow your chance.

4. Where to ask them out? Somewhere quiet

How to ask a coworker out and where you do it, are both really important. It is also very important to be sure if you can handle dating a coworker as there are many risk factors involved. Find a place where you both feel secure and at ease. Ask them to meet you somewhere with few or no people at all. They might feel pressured to say no or yes if you ask them out when they are surrounded by other colleagues. This is your only chance to ask them out, so ideally, you don’t want to blow it. 

If you can see they are busy, that’s not the right time to pop the question. You don’t want them to pay less attention to you when you ask them out on a date. Take your time, but try not to take too long. (You don’t want your coworkers to suspect you, do you?)

If you can’t find any apt place in the office grounds and meeting them outside is not a possibility, you can always ask a coworker out over a text.

Related Reading: 55 Awesome Date Ideas For Friday Night!

5. If you’re thinking about asking out your boss/subordinate, don’t

thinking about asking out your boss

Workplace romances, as exciting as they sound, can quickly turn into nightmares. It’s risky enough to ask a coworker out, but if the person you want to ask out is your boss or subordinate, it’s a no-no.

If your boss is attractive and you have feelings for them, keep them to yourself. Things could go wrong in more ways than you can think since you are not in an office romantic drama. No one would want to engage in casual or intimate conversations with you as they’ll worry that the boss will find out. Dating your boss could make you a pariah. Also, they hold the authority here, therefore if you choose to mix personal and professional lives, it may risk your livelihood. Workplace awkwardness is something we don’t want if your supervisor rejects you.

It’s worse to ask out a coworker who is your subordinate. Because you are the employer, your employee may feel pressured to comply in order to keep their job. Overstepping the line between employer and employee is not acceptable. You don’t want your employee to keep searching if their boss likes them romantically in the working hours, do you? This could be a source of harassment for your subordinate and foster an unsafe and hostile work environment for them. Additionally, it is incredibly disrespectful and highly likely to ruin your reputation and business. 

According to research, women were more cautious and less motivated than men about their involvement in workplace romance. Men had a more favorable attitude toward it. Studies also illustrated that workplace romance in the form of mutually committed relationships positively affected employee performance. The partners worked hard to create a favourable impression on their employer.

6. Be yourself

Your coworker spends a lot of time around you, just like you do. Even if you have never spoken, they are aware of you and at the very least have noticed you. If you try to act fake around them, they will notice. So, the best course of action here is to be yourself. It’s quite normal and acceptable for you to feel anxious, but don’t mask it. Dealing with a crush at work can be a little difficult.

Simply take a deep breath if you are feeling anxious and keep going. They must be experiencing the same feelings at the moment if they are also interested in you. Asking someone out on a date requires confidence

7. Here’s how to ask them out on a date

Here it comes, the hardest part. You might feel a lot of anxiety and trepidation. The process may be daunting. But you don’t have much to lose, though, in the end. The worst-case scenario is that they will graciously decline your request and say ‘no’.

Here’s how to ask a colleague out: “How’s your day going?” is a good way to start a conversation. Ask “What are your weekend plans?” If they seem free, go ahead with – “Would you like to go on a coffee date this weekend?” or “Do you want to go watch some movie over the weekend?” If they are interested, continue with “Great, what time would you like to meet?” or “Great, let us plan it out”.

Let them know it’s okay if they are busy or uninterested before you excuse yourself gracefully.

8. Ask a coworker out for lunch or coffee – but casually

You can always choose to ask them out discreetly if you believe that asking them out directly will lead to awkwardness between you two. It can be helpful to ask a coworker out for lunch or coffee(Trust me coffee date is the best idea for the first date, it will help you to chat and there will be near to zero awkwardness), go to a movie or museum on the weekends, or just ask them if they’d like to attend any local festivals with you – without making it sound like a date.

You can ask a female coworker to hang out with you if they do not have any plans for the weekend. You can ask a male coworker out too. Additionally, getting to know them and socializing with them outside of work could be helpful in taking things forward (and can also be counted as an unofficial date).

9. Here’s how to ask a coworker out: Have friendly conversations first

Your ability to comprehend them, their likes and dislikes, and their hobbies will improve the more casually you converse with them. Your relationship with them can grow stronger by engaging in polite conversation with them over coffee or lunch breaks. The more time you spend talking, the more you learn about them and vice versa. You may be able to ask them out eventually as a result of these amicable conversations.

Don’t hesitate to ask a coworker out for drinks if you are friends. But make sure you are a little casual about it. Our reader, Nathan, a 29-year-old medical technician, likes Pat, but they never really hung out after work. He shares, “So one day, I decided to ask Pat if he wanted to chat over a coffee after work. It worked, he said yes, and we talked for hours.” You can also ask if they want to celebrate a project’s completion with a few drinks this weekend. Keep it as casual as possible so that if they say no, neither of you will be embarrassed.

Related Reading: How To Date A Girl At Work? Follow Our Tips!

10. Don’t rush anything 

Make sure you understand what you are getting involved with. Finding a balance will be necessary if you discover that even the coworker is interested in you. Although it’s not against the law, some ground rules must be established before dating is initiated at work. Office romance can go sour at any moment, you never know. Don’t expect them to answer you immediately. They might need time to process your feelings and align them with the fact that you’re colleagues.

The risk of dating at work must be carefully considered by both of you. If things start to go south, it might have an impact on your career development, therefore it’s important to be smart about it. Don’t rush things for the sake of a moment’s excitement. That’s our most important tip on how to ask a colleague out.

Office Affairs

11. Don’t let your feelings affect your work

If you are interested in someone, they are always on your mind but in your case, they are always around you too. It is very normal to feel butterflies when someone you are interested in passes by. Will things work out? Will things remain the same if they don’t? ‘How to ask a colleague out’ becomes your mental refrain. You must not allow your emotions to compromise the caliber of your work. As it may hinder your professional development, make a very conscious effort to keep your mind and heart on opposite poles. Office affairs can spell trouble for you.

Jules, a 24-year-old software developer, went through a rejection recently when she asked out a coworker. She shares her lesson, “There may be a time when you don’t want to see or speak to your coworker because you tried to ask them out and it didn’t work out. But treat their ‘no’ as professionally as you can, there’s nothing to be embarrassed about. You can’t not interact with them if they are on your team. So don’t let this interfere with your professional life.”

On the flip side, they may have said yes. In that case too, don’t hover around their desk to talk to them when they’re trying to work (and when you should be working too), don’t gaze into each other’s eyes during office meetings, don’t flirt with them in front of others all the time. Maintain their and your own dignity at work.

Does My Crush Like Me

12. Don’t discuss work on a date

You may have mutual acquaintances from the office and belong to the same professional network, but when you ask a coworker out for drinks, keep your workplace or team gossip to yourself on the date. Your time with them right now is personal.

It’s crucial to maintain a healthy work-life balance. You could come across as having no life outside of work if you spend your date talking about work or colleagues or your boss. Moreover, it is somewhat off-putting.

13. Know when to stop

Leave it alone if a coworker tells you they are not interested in you. You can’t make someone fall in love with you by repeatedly asking them out. Additionally, it will create a hostile or unpleasant work environment. You only get one chance to take a shot, so if it doesn’t go well, it doesn’t go well. Don’t take it as a challenge and start bugging or flirting with them. Not only is this an indecent thing to do, you also risk losing your job if they file a complaint with the HR.  Can a “No” mean something else? NO. its a very straightforward answer.

Just smile and tell them you accept their response. Don’t make them anxious about your reaction. They deserve to have a safe environment to come and work in. Although it is initially painful, ease the tension between you two by being as polite as you can and carry on with your normal behavior after this.

Key Pointers

  • Casually asking a coworker on a date
  • Know your company’s policies before taking any decision
  • Keeping your personal and professional life separate, know when to stop
  • Do not take advantages of your position in the company to harass your subordinates

Remember to check your company policies before you make a move on a coworker. It is not worth risking your job for a casual fling. 


1. Is it appropriate to ask a coworker out?

It is not inappropriate to ask a coworker out but if it’s your subordinate or your boss, it is better to stop. It consists of its own set of risks and as long as you are ready to take them and if it’s truly consensual, it is alright. Keep in mind that the power dynamics between you two are skewed, and if you know it’s only a fling, it’s not worth jeopardizing your job.

2. How long should you wait to ask a coworker out?

If you keep wondering how to ask a coworker out, but are not sure ‘when’ to do it, wait until you are completely sure about your feelings. Once you think it’s the right time and place and an opportunity arises, you can ask out your coworker. The results may not always be positive so it is better if you are prepared for the aftermath.

3. How do you know if a coworker likes you?

You would know when someone is interested in you from their body language and the way they talk to you or behave around you. If you are still unsure, you can talk to mutual friends or ask the colleague directly.

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