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21 Ways to Ask a Coworker on a Date

21 Ways to Ask a Coworker on a Date

It might shock you to hear this, but one third of your life is spent at work. The average person spends 90,000 hours in a workplace during their lifetime. 

It’s no wonder then that so many people end up dating their coworkers.

If your colleagues are the people you are around most often, it is only natural that you get to know them well and that flirtationships begin to blossom. 

Plus, nothing makes a boring day at work more exciting than making eyes at your new good-looking coworker over the top of your computer screen.  

And, as long as you respect your workplace policies on socializing with coworkers, there is nothing wrong with developing feelings for someone who just happens to work in the same building as you. 

That said, it is obviously risky to ask a coworker on a date.

If they say no, you’ll still have to make small talk by the water cooler on a regular basis, which could be awkward. 

For your best chance of landing a date with someone you work with, ask them to get together to do something laid back and casual.

If things go well, you can up the romance. 

 

21 ways to ask a coworker on a date

  1. Hey, would you be up for grabbing a drink sometime after work?
  2. Are you watching the game later? I’d love to join if you are. 
  3. I’ve really enjoyed getting to know you over the last few weeks. Would you be up for getting together outside of work sometime? 
  4. I hope this isn’t too forward, but would you like to grab a coffee together sometime? 
  5. Do you have plans for lunch today? 
  6. I was thinking of stopping by the bar after work today. Would you like to join me?
  7. I’ve loved our chats in the break room. Any chance you’d want to continue them over a beer sometime? 
  8. You’re single right? If you’d be interested in grabbing a bite sometime, I’d love to get to know you a bit better in a more casual setting. 
  9. You know that place I was telling you about on Main Street? There’s a great band playing there on Friday, and I was wondering if you’d like to go see them with me. 
  10. So, I hope you don’t think I’m overstepping, but I’d love to take you out sometime. Would be interested in getting together outside of work? 
  11. I’m a little scared to ask you this because I hope I haven’t misinterpreted anything, but would you like to grab a drink with me this weekend? 
  12. I swear I won’t make things awkward if you aren’t interested, so there’s no pressure to say yes at all, but would you want to go see that movie we’ve been talking about at the cinema this Friday after work? 
  13. In addition to being beautiful, you’re highly competent and intelligent, and I’ve found myself developing real feelings for you that I can’t keep to myself any longer. Can I please take you out for dinner on Thursday?
  14. So, when are we going to get together to talk about how we really feel about all our colleagues? 
  15. Hey there, my favorite coworker, any chance you want to be my favorite coworker over a drink this weekend? 
  16. Hey! So…you know that Friends marathon we keep joking about having? I’m being deathly serious about all that––want to come over and make popcorn and binge watch season 1 sometime? 
  17. Hey, I hope this isn’t weird, but I noticed you always come to the office with climbing gear and I’m short a climbing partner this weekend. Would you like to go the climbing gym together on Saturday? 
  18. Hey! I got your number from Samantha. Hope that’s okay! I’ve loved talking to you during lunch breaks and was wondering if I could take you out for a proper lunch (no Tupperware involved!) this weekend. Let me know  
  19.  Hey! I heard you’re big into hiking (and I also heard you’re single and think you’re really pretty), so if you ever wanted to go hit the trails with another enthusiastic, single hiker, you know where to find me
  20. Hi I just wanted to tell you how much more enjoyable I find going into work ever since you started at the company. I always look forward to seeing you in the morning and to talking during coffee breaks. I really think we have the potential to be something, so if you feel the same, I’d love to treat you to a coffee that isn’t instant sometime. 
  21. Hey! It’s Ben from the office. Were you serious about wanting to see that cove I was telling you about? I was thinking about heading down to the coast on Sunday, so let me know if you’d like to join! 

 

How to ask a male coworker out

In 2022, it is just as accepted for a woman to ask out a man as it is for a man to ask out a woman. 

However, because of the continued influence of traditional gender roles, it can be intimidating as a woman to approach a man––let alone a male colleague––and ask them on a date.

But if you’re a woman and have developed a crush on a male coworker, don’t let old-school gender roles stop you from making a move!

After all, who doesn’t want to date a smart girl

Many men feel uncomfortable asking out their female coworkers because they want to make them feel respected as professional colleagues and because they are aware that unwelcome advances are often considered harassment.

For this reason, it may well be that a male coworker is waiting for you to make the first move. 

Here is a list of a few things you could say to get the ball rolling. 

 

1. Hey, would you be up for grabbing a drink sometime after work?

This is a straightforward way to ask out a male colleague. It doesn’t beat around the bush or cause them to question whether you’re asking them out. 

Basically, what this way of asking out a male coworker means is, “From what I’ve learned about you so far, I think you’re interesting, and I would like to get a drink with you to see whether or not we are romantically compatible.” 

 

2. Are you watching the game later? I’d love to join if you are. 

If you know that the male colleague you are into is a big sports fan, you could ask him if you can join him to watch a game sometime. 

Watching a game (preferably in a local sports bar) is a super casual way of spending time with someone you want to get to know better. 

There’s no pressure to talk the whole time, and if you decide you aren’t really that interested after all, you can just talk about the game, and you won’t even have wasted an evening. 

While most people who are planning to ask someone out worry about things like how many days in advance to ask for a date, when you’re suggesting a casual get together with a colleague, you don’t need to think about these kinds of formalities. 

 

3. I’ve really enjoyed getting to know you over the last few weeks. Would you be up for getting together outside of work sometime? 

This phrasing emphasizes that you are inviting your colleague to change the way you hang out by taking your relationship of the workplace and into your normal, private lives. 

It is helpful to acknowledge this crossover from colleagues to personal acquaintances (with the potential to be more) when asking a coworker out on a date. 

 

4. I hope this isn’t too forward, but would you like to grab a coffee together sometime? 

If you are worried that the male colleague you have a crush on might not be into you or might think you are being presumptuous by asking them on a date, you can preface your question with the disclaimer, “I hope this isn’t too forward.” 

This shows respect for their right to say no and that you are sensitive to the professional boundary you are asking them to cross. 

 

5. Do you have plans for lunch today?

If you like one of your male colleagues and would like to give them a sign that you’re interested in them romantically, why not just ask them if they want to eat lunch together during your break from work? 

Whether you’ve brought something from home or are going to your workplace cafeteria, sitting together over a meal in a very casual setting is a great way to get to know someone without the pressure of a formal date. 

Since you already spend so much time together, there’s no real need to worry about how long a date should last.

Even twenty or thirty minutes will give you a better idea of whether you’d like to pursue things further. 

 

6. I was thinking of stopping by the bar after work today. Would you like to join me?

When you’re asking someone out, it can be easier to let them know you have plans to do something and ask whether they want to join than it is to ask them expressly whether they think the two of you should do something together. 

By telling them you’re going to the bar either way, you’re also letting them off the hook in terms of you their responsibility for you enjoying your evening. 

If you phrase your interest in getting together outside of work as a situation in which they just happen to join you at a place you’ll be at regardless, you’re letting them know that you having a good evening doesn’t depend on them. 

 

7. I’ve loved our chats in the break room. Any chance you’d want to continue them over a beer sometime? 

This is a simple, mature, and respectful way to ask out a male coworker. 

By beginning your question with “Any chance…” you are letting them know that you don’t take it for granted that they will say yes. 

 

8. You’re single right? If you’d be interested in grabbing a bite sometime, I’d love to get to know you a bit better in a more casual setting. 

When you want to ask a male coworker out, it is always best to check whether they are single first. 

The last thing you want is a hostile girlfriend eyeing you up suspiciously at your next office Christmas party. 

Once you’ve established that he isn’t in a relationship, you can suggest getting to know them in a casual environment. Since you’ve already made it clear that you’re interested in him––you wouldn’t have asked if he were single otherwise––you don’t have to make fancy plans. 

A causal place for a bite, like a burger bar or deli, is a great place for a low-pressure first date. You will know a date went well if your male colleague asks you on a second date by the end of it. 

 

9. You know that place I was telling you about on Main Street? There’s a great band playing there on Friday, and I was wondering if you’d like to go see them with me.

Asking someone to go on a first date to do something specific takes the pressure off the “date” element of the evening. 

If you both like a band, you’ll enjoy going to see them regardless of the company. 

So, if you realize you aren’t compatible, there’s no harm done and it will be less awkward in the office the next day, because at least you’ll still have a common interest to talk about!

How to ask a female coworker out

If you want to ask a girl out but are wondering whether asking a coworker out is harassment, it is important to read up on your workplace’s policies on socializing between coworkers. 

Most employers are broadly supportive of office romances between colleagues so long as both parties are consenting, no one person has direct professional authority over the other, and the relationships do not interfere with workplace productivity.  

However, make sure you double check your company’s policy! Also, always accept “no” the first time. 

If you like a female coworker and you ask her out and get rejected, don’t continue to pursue her, and certainly don’t make inappropriate comments or make her feel unsafe in her place of work.

Here are a few respectful ways you could ask a female coworker to hang out. 

 

10. So, I hope you don’t think I’m overstepping, but I’d love to take you out sometime. Would be interested in getting together outside of work? 

When asking out a female colleague, it is a good idea to add a disclaimer before the question. 

By telling her you hope she doesn’t think you’re overstepping, you’re showing her that you respect her right to say no and to draw a boundary between her personal and professional lives. 

This will allow her to consider whether she wants to take you up on your offer without worrying that she will face consequences––professional or otherwise––if she declines. 

 

11. I’m a little scared to ask you this because I hope I haven’t misinterpreted anything, but would you like to grab a drink with me this weekend? 

Beginning your request for a date with a female colleague by humorously adding that you’re a little scared to ask her out shows your vulnerability. 

Whether she is into you or not, she will appreciate this insight into how you think and will feel closer to you personally. 

In all likelihood, if you are sensitive enough to look into how to best to ask the coworker you’re crushing on out, you haven’t misinterpreted anything, and you will only be gaining plus points by showing off your sensitive, thoughtful side. 

 

12. I swear I won’t make things awkward if you aren’t interested, so there’s no pressure to say yes at all, but would you want to go see that movie we’ve been talking about at the cinema this Friday after work? 

If you’ve already been speaking to the woman you like about a specific event, exhibition, or movie that you’re both interested in, you have an easy in to ask her if she’d like to go see that with you. 

By telling her in a lighthearted tone that you won’t make things awkward if she isn’t interested, you’re letting her off the hook easily if she doesn’t want to date you. 

And if she does, you’re just showing her that you are a kind and considerate person who would never want her to feel like she has to do something she doesn’t want to. 

 

13. In addition to being beautiful, you’re highly competent and intelligent, and I’ve found myself developing real feelings for you that I can’t keep to myself any longer. Can I please take you out for dinner on Thursday?

If you’ve been crushing on one of your female colleagues for a long time and have developed a close workplace friendship––or at least a good working relationship with her, you can lay your cards all out on the table when you ask her out. 

By expressing exactly what it is that you like about her, you are giving her a clear idea about how committed you would be to making a relationship work and showing her that you aren’t just asking her out without thinking.

 

14. So, when are we going to get together to talk about how we really feel about all our colleagues? 

If you don’t know the female coworker you’ve developed a bit of a thing for all that well, but you sense that you have a similar sense of humor and similar opinions about many of the goings-on in the workplace, you can ask her out using this funny line. 

 

15. Hey there, my favorite coworker, any chance you want to be my favorite coworker over a drink this weekend? 

Often when you develop a crush on a coworker there’s a lot of flirty, workplace banter involved. 

If you have told the girl you like that she’s your favorite coworker, you might try out this line when asking her out. 

Keeping the light-hearted, funny tone of your conversations going will surely make hermore likely to say yes, because you are reminding her of how much fun the two of you have together.  

 

How to ask out a coworker over text

If you want to ask out one of your coworkers but can’t quite find the right time to do so in the office without it being awkward or drawing attention, sending them a text is often your best bet. 

However, it can be difficult to convey the right tone over text, especially when it comes to something as potentially sensitive as asking out a work colleague. 

Here are a few things you could text a coworker to ask them out on a date. 

 

16. Hey! So…you know that Friends marathon we keep joking about having? I’m being deathly serious about all that––want to come over and make popcorn and binge watch season 1 sometime? 

If you have already joked in person about getting together with a colleague you have a thing for, it shouldn’t be too hard to ask them out over text. 

After all, people only joke about things there is some degree of truth to, so if you and a colleague often talk about meeting up to do something, chances are that there’s a genuine desire to do it on both sides. 

They won’t be trying to get out of your date, since they’ve clearly been hoping you’ll ask. 

This cute text, which can of course be adapted to fit a wide variety of circumstances, allows you to transform a private, in-person joke into real-life plans. 

 

17. Hey, I hope this isn’t weird, but I noticed you always come to the office with climbing gear and I’m short a climbing partner this weekend. Would you like to go the climbing gym together on Saturday? 

If you notice that a coworker you’d love to get to know better is into one of the same things you are, use this to your advantage! 

If you don’t get much of a chance to talk to them at work, you could send them a quick text telling them that you’ve noticed they share an interest of yours. Then, it naturally follows that you would suggest getting together to do that thing. 

Whether it’s sport climbing, bowling, or a video game, sharing an interest in an activity is an excellent way to get to know someone. 

 

18. Hey! I got your number from Samantha. Hope that’s okay! I’ve loved talking to you during lunch breaks and was wondering if I could take you out for a proper lunch (no Tupperware involved!) this weekend. Let me know  

If you are texting a colleague who hasn’t personally given you their number, it is always good to tell them where you got their contact details from. 

If you’ve gotten to know your colleague during lunch breaks, you could ask them out by making a cute reference to the time you’ve shared together, for example, eating out of Tupperware. 

 

19. Hey! I heard you’re big into hiking (and I also heard you’re single and think you’re really pretty), so if you ever wanted to go hit the trails with another enthusiastic, single hiker, you know where to find me

When asking a work colleague on a date over text, it is probably wise to be clear about the fact that you are asking them to get together because you like them in a romantic sense. 

Especially if the activity you are suggesting is not necessarily romantic in nature, you don’t want to confuse them by having them think you’re just wanting to get together as friends. 

Complimenting their looks and making reference to their single relationship status will certainly get the right message across. 

Additionally, the fact that you have checked her relationship status makes a good impression since it shows that you aren’t someone who wants to date married women, which speaks to your morals.

 

20. Hi I just wanted to tell you how much more enjoyable I find going into work ever since you started at the company. I always look forward to seeing you in the morning and to talking during coffee breaks. I really think we have the potential to be something, so if you feel the same, I’d love to treat you to a coffee that isn’t instant sometime. 

If you want to sincerely express your interest in a colleague over text, letting them know how much you look forward to seeing them every morning is a sweet thing to say. 

You can combine serious and humorous feelings to show that even though you genuinely like them, you also don’t take life too seriously. 

Joking about treating a work colleague to a real coffee is a cute approach to asking someone out if your place of work only has low-grade coffee. 

 

21. Hey! It’s Ben from the office. Were you serious about wanting to see that cove I was telling you about? I was thinking about heading down to the coast on Sunday, so let me know if you’d like to join! 

It is common for people to express and interest in things they aren’t really too bothered about. And this is especially true when it comes to small talk in a work setting. 

So, if you suggested plans to a colleague you like and they seemed interested, it is a good idea to double check their level of interest via text. If they’re up for it, you can nail down plans.