Texting a Coworker You Like or Crush at Work [Guide]

You’ve developed a crush on one of your colleagues.

But how do you flirt with a coworker? How do you text your coworker outside of work?

You don’t want any trouble at work or an awkward letter from HR.

In this article you’ll discover exactly how to text that coworker you like without getting into trouble.

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Is dating a coworker a good idea?

In a lot of companies, dating someone in the workplace is not allowed. So before you do anything, I recommend you read up on your company’s policy on office romance.

By checking your organization’s rules and policies on romance, you’ll know for sure if dating and texting a coworker is inappropriate.

That said, A 2017 Stanford study shows some interesting data.

More than 15% of people in a relationship found their partner at work or via their work relations.

It makes sense, doesn’t it? You spend a lot of time at work. You see your co-workers regularly and have at least something in common.

There are some risks, however.

The pros:

  • Because you see each other so often, you know your colleagues quite well. Everyone is relatively reliable and trustworthy.
  • Thanks to the environment, you know how your coworkers handle pressure and deal with conflict. Which is great to know before you decide to date someone.
  • You can easily build rapport with someone without having to break up your routine.

The cons:

  • You first have to show interest and figure out if someone likes you back. If this goes wrong, you might expect some difficult talks with management.
  • If you’re dating someone at work and it goes wrong, you’ll be seeing that person 5 days per week. Which is not only uncomfortable, it could lead to awkward and even dangerous situations that threaten your livelihood. Depending on the circumstances, you could lose your job.

When is texting a coworker you like appropriate?

Showing interest in a coworker is risky business. There are several things you NEED to manage:

  • You don’t want to come across as creepy or pushy.
  • You don’t want to have a working relationship with someone that had to turn you down.
  • You don’t want everyone to know you are into that specific coworker.
  • You don’t want to create conflict or difficult work situations.
  • You still want to have a professional relationship with your colleagues.

Therefore, you have to be extra careful.

Texting a coworker outside of work should NEVER be your first step in trying to get her attention. It might feel intrusive and weird, and you don’t want that kind of situation at work.

It’s only appropriate to text a coworker outside of work if:

  • You’re already flirting back and forth.
  • You have a good reason to text her or mentioned you’re going to text her for a specific reason.
  • You’ve built some rapport one-on-one.

Texting her out of the blue is tricky. So first you want to make sure you have playful, slightly flirty interactions. This shows there is some mutual interest.

Next, you want to have a good reason to text. Not a random ‘hey what’s up.’ Preferably something your coworker is expecting.

For example, you talked about food and she mentioned she liked Indian food. You followed up with a flirty: ‘I know the best Indian restaurant in town. It’s a little secret no one knows. I should totally take you there sometimes.’ Based on her response you’ll know if she responds cold or positive.

Now you could spontaneously text your coworker:

Remember the place I told you about? I just saw they have a great new menu. We should totally go. Are you free on Friday?

Need some help on building an emotional connection with your workplace crush? Check out my next article (it’s about texting, but the principles apply to real life too):

What if you’re friends with your coworker already?

What if you’ve known her for some time and you even do stuff outside of work as friends?

What you feel as romantic and/or sexual arousal, she may see as strictly friendship.

The big difference is sexual tension.

You might feel it simply for the fact that you find her physically attractive.

But a woman usually needs more. She actually needs flirty and playful banter between the two of you. Maybe even some light touching.

If you’ve been meeting as friends but you secretly like her, first create these playful vibes between the two of you.

How do you find out if you’re in the friendzone or not?

Check out this video I made with 6 signs:

Best way to text a colleague outside of work

Remember, you want to avoid awkward situations at work at all costs.

And to get with your coworker, there are two hurdles you need to overcome:

  • You have to start texting your coworker without her wondering why on earth you are texting her outside of work.
  • You have to start flirting and showing romantic interest without creeping her out or crossing professional boundaries.

So which one comes first?

It depends. There are two routes to dating your coworker.

The first is creating a more flirtatious vibe in real life with your co-worker at work when you’re one-on-one and then moving to texting and meeting outside of work.

The second is meeting outside of work with your crush and other colleagues for fun social gatherings (and texting to arrange the details) and establishing a more flirty vibe with her during those gatherings.

The most important thing in both cases before you start texting a coworker is this:

Have good rapport with the person you fancy from work.

Without good rapport, your texts will only feel strange and will likely create awkwardness in the office.

Only if the two of you DO get along well, can you send her an after work text.

So where do you start?

1. Invite your coworker to a social gathering

One way is by inviting her to a social gathering with other co-workers.

“But Louis, how is that romantic?”

It’s not. Before you even get close to dating, I strongly advise you get to know your crush outside of work and see if she’s truly a fit for you. So test the waters first.

Hey, Josey. A bunch of people from work are going to get together for drinks on Friday evening. We’d love it if you could join us. Let us know if you can make it!

If she’s busy she may take a raincheck. But it’s highly likely she’ll show up for a gathering eventually. And when she does, pay close attention if she’s giving you any signs of interest.

Perhaps form a team for a friendly pool tournament or pub quiz, so that you’re forced to spend time together.

Is she single and do the two of you really hit it off? Send her this text the same evening:

Hey, Josey. I had a really good time with you tonight. And this may sound a little crazy because we’re co-workers, but I’d like to take you out sometime. Just the two of us. No hard feelings if you’d rather not. Anyway, have a great weekend!

The beauty of this text?

  • It’s complimentary.
  • You’re showing that you’re aware of the risks involved of dating someone in the workplace.
  • You’re not trying to force anything by telling her it’s okay to reject you.
  • You’re clear in your intentions. It’s about exploring chemistry, not a casual hook-up.

Which reminds me, if you just want to jump into bed with your colleague, forget it. Sex is not worth the potential risk of losing your job.

2. Have one-on-one time at the office

Depending on the layout of your office, it shouldn’t be too difficult to have some natural one-on-one time with your crush.

  • If she’s in an individual office, you might walk in with some work-related question. Which leads to some casual talk.
  • Maybe you have a meeting with others and both arrive early or stay afterwards for a bit.
  • You might meet her by coincidence in the hallways or at the coffee machine. Make sure to have some question or small talk ready.
  • You could randomly invite her for a lunch if you’re grabbing something outside. Nothing weird.

There’s usually enough moments in the day to get to know each other a bit. It might take several weeks or even months, but that’s fine if you’re seriously interested.

When you build some rapport, you can move towards getting slightly more flirty. And when she flirts back it’s a sign you could move things to text and meet outside of work.

How to flirt with a coworker over text

Again, we need to manage risk. Imagine you have a coworker that you’re just friendly with, and you’re texting her.

All of a sudden you start flirting. That’s risky! What if she isn’t in to it. You might just have created a very awkward work situation with a colleague.

There are a couple of strategies to flirt with your coworker over text with as little risk as possible:

1. Start flirting very carefully and monitor her response

One way is to make a small flirty comment and pay close attention to her reply.

If she replies back in a flirty or playful way, you’re good.

You can slowly start flirting a bit more. Take your time. Don’t go all-in. Monitor her responses every time.

If she replies dryly or ignores your playful remark, you should be careful and back off for a bit.

So you’re coming to the office party as well right?

Yeah totally!

You’re not going to wear that Christmas sweater you wore last year right? I can’t promise I won’t stare at Rudolph’s big red nose all the time!

Haha, I bet you would. Well, Rudolph’s already staring at me from the closet for a couple days, so who knows…

This is an example of a quite harmless joke. But still it’s playful.

And her reply is also playful. So that’s a good sign.

Check out this article with more on flirting over text:

2. First flirt with her one-on-one

If you’re one-on-one (whether it’s at the office or at some party) and you flirt a bit, it’s way easier to see if she likes it.

Since texting lacks body language and tonality.

And since you’re seeing each other quite regularly at the office, it isn’t weird talking to her and adding a bit of playfulness.

Is she receiving it well and being playful back? Great.

When you move to text, it’s only natural that you continue your playful and flirty way of communicating.

3. Become the flirty guy

This is more important than you might expect.

Imagine you’re a quiet, more introverted guy, and you like your coworker. The step to going from casual talk to flirting might be huge.

Even more important: your coworker might not expect it at all. Because it’s so different from how you normally communicate.

This also means it might very quickly be awkward or feel inappropriate.

Now imagine the typical flirty guy at the office. He flirts with everyone. It’s just his way of being. He doesn’t even have a romantic intent.

Everyone will accept it. It’s just a fun guy. And it doesn’t even mean anything. Although, let’s be honest, it IS attractive.

Which of the two will have an easier time pursuing a coworker crush? The latter of course.

So do you have to turn into the office Don Juan? No.

However, it does help a lot if you become more open and playful in your way of communicating with everyone.

How to tell if a coworker is interested through text

Wanting to know if a colleague likes you over text is already a red flag. You shouldn’t be looking for signs of interest over text. You should be looking for signs of interest in real life.

After all, real-life chemistry is the only type of chemistry that counts. And you already see each other quite regularly at the office.

Before you decide to take the plunge, wait until you feel fireworks in real life.

That said, it’s still good to know if she likes you over text.

That knowledge can help you from ruining the rapport you built up by accidentally talking about stuff she seriously dislikes.

The three signs that really show me if a girl likes me are the following:

  1. She replies quickly to my texts.
  2. She tells me things without having been asked.
  3. She asks me questions.

If you can spot these signs in your convos, she’s probably into you.

For 19 more signs on how to recognize if someone likes you over text, check out this article:


Dating a coworker makes total sense. But it’s risky as well.

Before texting a coworker, make sure you build rapport in real life. And preferably have at least some indication she’s interested in you, based on some playful real-life conversations you’ve had together.

When you text your coworker, build the playfulness up very carefully. Let your coworker also invest. You want to only move forward if you have clear indications that she likes you.

This way you prevent awkward situations at work.

Louis Farfields

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