How to Casually Ask a Coworker Out (coffee or drinks)

March 30, 2023

Navigating the dating scene can be difficult under the best circumstances, but the workplace can add an extra layer of complexity. With the amount of time we spend at work, it's no surprise that romantic feelings can develop between coworkers. 

If you find yourself crushing on a colleague and want to know how to casually ask them out, this guide is for you.

One example if you're already texting them is to meet up for coffee before work. You can mention you're picking up some for coworkers and need a hand but want to know if they want to tag along: 

"Hey I'm doing a coffee run tomorrow, do you want to grab one with me then help me bring them over?"

This gives an "excuse," which makes it casual as it takes the sting out of any rejection. We'll go over more examples of how to do this and how to ask them in person (if you don't yet have their number).

What to Know Beforehand

There are a few things to keep in mind before we start. Asking a coworker out needs to be done more cautiously, as you don't want to make future time spent together awkward if you get rejected. You may not want to "Rizz her up" like you would with someone you just met.

Gauge their interest

Look for subtle signs of flirting or indications that they enjoy spending time with you. Pay attention to their body language, tone of voice, and how they interact with you. 

Remember that some people are naturally more friendly and outgoing than others, especially if they have to be due to the nature of their job. It's essential to differentiate between platonic and romantic signals.

Get to know them better first

Get to know them personally by engaging in small talk and participating in shared interests or activities. This will help make it easier to ask them out and give you more to talk about if you go on a date. 

In most cases, you should text them for 1-2 weeks before asking them out.

Also, if you have work events, try to speak to them there as things will be a bit looser. This can help you two talk without being too busy with your job.

Keep it casual

When you're ready to ask your coworker out, keep the tone of the conversation light and chill. While being direct is ideal for cold approaching, it doesn't fit as well in this sense. Having a reason/excuse like asking (if you work in a restaurant) to grab a drink scoping out the new "competition" down the block. 

This approach allows your coworker to respond without feeling pressure and allows you both to test the waters before committing to something more serious.

Be prepared for rejection

No matter how well you plan or how strong your connection seems, there's always a chance that your coworker won't be interested in pursuing a romantic relationship. Brush it off and move on. 

If you can, stay friends with them- as they may have friends themselves they could set you up with.

Company policies

Some organizations have strict rules prohibiting dating among employees, while others may require you to disclose the relationship to HR or a supervisor. Make sure you're aware of these guidelines and prepared to follow them.

You may also want to avoid asking out your boss (or someone you're a boss of), as things could get messy.

Examples of What to Say

Unless you work in a restaurant like the example above, asking them out for drinks will be a bit less casual since it's an obvious "date." Therefore, be straightforward if you go this direction. Something like 

"hey would you want to grab a drink this weekend?" can be done in text or person. 

It may be challenging, but it's quick and puts out the guesswork.

There's also the choice of inviting them out as a group first. It's not exactly a date, but it's time spent getting to know each other outside the office. 

"Kate and a few of us are meeting up after work tomorrow if you want to tag along.

Any time you can spend with them in a laid-back environment makes asking them out easier.

Finally, there's the option for coffee (like in the indirect example in the intro). 

"Want to grab a coffee before work?

If you want to gauge interest, go alone but send her a text asking if she wants you to pick her up one (though at least ask some others so it's not weird).

You can also do work-related things together without being part of your job: 

"hey I have to drive out to UPS to pick up some supplies; want to keep me company?".  

Of course, make sure it's clear this isn't some work task that's expected of them.

If you're reading this, you probably prefer not to ask directly for a yes or no answer. This is fine, as it's better than chickening out and not doing it at all. 

If you're young and haven't dated much, experience is everything- but try to not get too invested in it working out with any one person. For more examples (unrelated to her being a coworker), check out How to ask a girl out for coffee.

How to Ask Out a Coworker Casually Over Text

This depends on your age a bit, but we are all basically at that point where text is deemed normal in almost any scenario. Honestly, it's recommended. Ask them out by first talking to them and seeing how receptive they are, then text: 

"we should hang out sometime.

There's no reason to make it more complicated than that.

That being said, naturally increasing your interactions with them will still be a more suitable option. Most of the coworkers I've asked out happened rather organically. After all, there's no rush since you'll see them regularly anyway.

If you don't have their number, talk to them through social media and go from there. Try not to push it, though, and first have a handful of conversations to see how receptive they are.

If they're engaged in what you're saying, have thoughtful replies and start conversations themselves- ask for their number. Or, better yet, offer yours: 

"here's my number btw I dont think I have yours added yet.

If they're not very receptive or talkative- shake it off. There's no reason to ever get hung up on any one person or continue pursuing a lost cause.

Go For it!

As I suggest with cold approaching- success comes from the action, not the answer. Asking someone out is always difficult when you're new at it, but the world opens up to you when you get some experience. 

Putting yourself out on the line like that isn't easy, so you should be proud of doing so regardless of the result. Best of all, it'll be a bit easier next time too.

Lastly, check out how to approach a girl that likes you if you already know she's interested. It goes over some direct method which may help make the process easier.

Best of luck, and don't sweat it!

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