Should you date someone from work?

Is it okay to date someone you interact with on a daily basis? Will it be too awkward if you break up?

So you’ve decided you want to date someone from work.

It happens to many of us, at one point or another.

When you spend every day with the same group of people, you form bonds with them. Especially at work or in university classes where you and your peers frequently team up to solve problems, it can be easy to develop feelings for someone you suspect you may be compatible with.

However, you have almost certainly heard the advice that you should never date someone from work in case things get messy. Breakups can cause a maelstrom of emotions that can be hard to manage in a professional or a school environment.

So… what shall you do?

To date a coworker, or not to date a coworker?

That is the question!

And it’s what we’ll be figuring out today.

In this post, we’re going to cover…

  • understanding why people say you should never date someone from work,
  • recognizing the worst-case scenario if you were to break up,
  • determining whether the reward is worth the risk, and
  • learning how to avoid as much potential awkwardness as possible, no matter what you choose.

Before we cut into the meat of the issue, however, we need to take a step back.


Why do people say you shouldn’t date someone from work?

Most of the time when you hear this advice, it’s coming from a place of good intentions.

Your friends are likely trying to gently bring you back down to reality with reminders that not every relationship works out for the best, and sometimes breakups can get messy.

On the surface, they may be right.

Dating coworkers or peers from your university cohort, for example, opens you up to potential awkwardness down the line.

Yes, you may break up. And yes, it may change the group dynamic.

But… that’s okay, yeah?

Sure, we want to be skillful about how we relate with others.

But once we’ve applied skill, if things don’t work out, that is generally totally okay, a learning experience worst-case scenario. ;)

In this article, we’ve been talking about overcoming fear of failure. But if you often find that a lack of confidence is holding you back, you should definitely download our free ebook.

In the ebook, we discuss a variety of techniques you can use in your dating life to boost your confidence and become a Benevolent Badass. Yay!

Once you’ve checked out this free ebook, read on to find out why it’s almost always going to be better to act with confidence and bravery, and take the leap.

Let’s dive in!


Step 1: “What’s the worst that could happen?”

This question sounds simple, but it’s key!

Before you proceed in any work-related situation, do take a moment to think through things.

Keep in mind the following:

  • Some workplaces don’t like interoffice romances. Would your job or hers be at risk if you began a relationship?
  • Emotions are sometimes difficult to manage during passionate beginnings or painful endings. Would your work be affected if you were to get swept up?

If the idea of pursuing your workplace romance makes you wonder if either of you could be jeopardizing your futures, you should absolutely take caution with the decision of whether to proceed.

If you do proceed, be sure to discuss the situation and possible risks with her, too, so you both approach things calmly and rationally from the very beginning.

That way, you have started a strong basis of working through situations with calm logic together.

But, in most cases, there are no workplace rules preventing coworkers from being together. Therefore, your future and hers would not seriously be at risk by starting a relationship.

Which means…


The worst thing that can happen is that you may feel awkward at some point.

That is absolutely something you can handle!

As the logical, analytical creature you are, you already possess the tools you need to overcome challenges and cope with setbacks, should any occur.

Unless we’re talking serious bodily harm as a consequence, fear is a tragic reason to avoid doing something your heart truly wants to do.

Part of the human experience is to learn and grow when things don’t go according to plan.

Feeling awkward is just a byproduct of being out of your comfort zone.

Instead of worrying, “What if it doesn’t work out?” you can ask yourself…

“What if it does work out?”

What if it’s actually amazing?

If you do decide the reward is worth the risk, move on to Step #2!


Step 2: Remember the most important part of any relationship:

No matter what, be a person who treats others well AND who associates with others who do the same.

Drama and awkwardness happen when people in a relationship act immature or petty.

By conducting yourselves with respect, wisdom, and grace, the two of you can bypass most of the potentially painful or uncomfortable situations that may arise.

Even if you break up, the separation is much more likely to be amicable and smooth if you have a strong foundation of treating each other with kindness.

This step is important not only for the health of your relationship, but also for the group dynamic of the community you are both involved in.

At work, for example, after a breakup, your coworkers may feel forced to “choose sides” if there is apparent drama that carries over into the workplace.

Or, if the two of you stay together and the relationship is strong, your coworkers may need time to adjust to the new group dynamic where the two of you function as an item.

By keeping things respectful with everyone involved, you will be eliminating much of this potential for awkwardness.


It’s a good idea to take things slowly.

Dating a coworker or someone within any close-knit group does carry an inherently higher risk than dating someone you don’t interact with on a daily basis.

That is simply how it is.

That’s why it’s wise not to rush just because you already know each other.

Instead of leaping in with both feet, take your time and enjoy the process of getting closer at a gradual pace.

This means it’s wise to take the physical side of your relationship slowly, too.

Physical relationships compound feelings that already exist, which tends to accelerate the speed at which relationships develop.

Even if you go into a relationship thinking you’d like to take things slowly emotionally, it’s hard to follow through on that plan once you’ve made things physical.

That’s because with physical intimacy, it’s likely that one or both of you will develop much deeper feelings for the other person.

This happens even in one-night situations where neither party expects to develop feelings. So it’s especially true when you’re starting from a place of building a real relationship together.

Take your time and savor the experience of truly getting to know your partner.

Taking things slowly gives both of you time to process and properly handle all of the feelings that may be emerging.

In turn, having the time to process these new and powerful emotions makes it much more likely your relationship will remain respectful and your group dynamic at work will remain peaceful.

You’ll likely find it’s more fun to slowly explore a budding relationship with your partner, too!


Conclusion on how to date someone from work

Man and Women Working - Date Someone From WorkDating a coworker is fine, as long as…

a) your jobs are not at risk, and
b) the two of you act with grace and treat each other (and your group!) with respect.

Just be sure to weigh your options carefully before proceeding. Once you have decided to take the leap, relax and know that, whatever happens, you will be able to learn and grow from the experience!

Let’s recap today’s post.

We covered…

  • evaluating the risks of starting a relationship at work,
  • realizing that, likely, the worst that can happen is a feeling of awkwardness, and
  • understanding that, if you treat each other (and the rest of your group) well, you are taking care of everyone involved.

But, the one point we should mention again, is…

Things very well could work out for the best!

So it’s almost always going to be worth it to gently pursue next steps in a potential fulfilling relationship.

Now, ready to take charge of your dating life, coworker-wise and otherwise? Our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead,” is a great first step here at Introverted Alpha.

Ready to elevate your dating skills to a whole new level? That’s exactly what we do inside our Launch Your Dating Life program. Talk with us in a 1:1 phone call (apply here), and we can see if the program is right for you!

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Kelly from IA
Kelly is resident writer here at Introverted Alpha, which is known as the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of our 22-page ebook inside the blue box just below.

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